Archive of Our Own ^beta

Chapter Text

“Left turn! Left! Damn it, Sarah, you missed the turn again.”

David Jacobs was having a rough day. He’d known for a while that his father planned to have him take over this particular delivery, but Harlem was much farther away than anywhere else he’d tried to get to at night. The darkness certainly didn’t help his (admittedly poor) navigational skills, and his sister Sarah’s remarkable inability to process his last-second directions compounded that.

The couple of weeks he’d spent doing the driving for his father wasn’t helping either. It had been too dark for him to ever recognize where he was going, and his father’s navigation had kept him from actually memorizing the exact route they’d taken. 

David wished he could use a flashlight to see the map better, but the entire goal of this operation was to not get caught. He held it closer to his eyes, squinting.

“Hey, what street are we on now?”

“Think I have a clue?” Sarah shot back. “My eyes’re on the road, not the signs. ’Sides, it’s too dark to read them quickly.”

David groaned and returned to the map, then peeked out over it. “Bear?”

“Yeah?” she replied, staring straight ahead.

“I think we’re lost. Scratch that. I know we’re lost.”

Sarah sighed noisily. “Son of a bitch. I’ll pull over in that alley so you can get your fucking head screwed on straight.”

David opened his mouth.

Sarah cut him off. “Ha, ha. No. Screwed on properly. I’m not letting you make that joke again.”

David groused, crossing his arms childishly as she carefully pulled into the alley.

Once she parked, Sarah made grabbing motions at him. “Gimme.”

He reluctantly handed over the map, taking the opportunity to look at his watch. “Shit!”

“Hm?” She looked up.

“It’s three forty-five.”

The faint color David could see in the dim light drained from her face. “Fuck.”

David rubbed his eyes with the heels of his hands. “We were supposed to be there almost two hours ago.”

“Shut up and let me concentrate,” Sarah said, shushing him dramatically. She intently studied the map, tracing out the route they’d drawn earlier. Her brow furrowed. “ Głupek ! Go check the sign on the corner behind us.”

David grumbled in protest but obliged, deftly hopping out of the truck and tipping his hat over his eyes. Hopefully, he couldn’t be seen by onlookers. But, even if he was, they wouldn’t be able to identify him. He peeked up at the sign. 170 th and Audubon . David hadn’t seen or heard of these streets before. He slunk back to the truck, sliding back in and quietly shutting the passenger door.

“So?” Sarah prompted.

“170 th and Audubon.”

“Damn it, bałwan , you got us to fucking Washington Heights! We gotta get out of here before the Irish hear!”

David did not panic. His years of training kept him calm and collected. “You figure out how to get where we’re going?”

“Pretty much,” Sarah answered.

“Step on it.”

She revved the engine, pulling out of the alley and speeding south to Harlem. David tipped his hat over his eyes and slid back in his seat, figuring he could catch a brief nap on the drive.

Sarah must’ve glanced over at some point. “Look at you, Mister Big Mob Man,” she mocked. “So mysterious in your long coat and hat. I’m so afraid.”

David didn’t look up. “I could kill you without opening my eyes, you know.”

She laughed. “You’d be dead before you got your gun out. I’m not stupid, you dewdropper. You know the only reason I’m not doing these runs myself is because I’m not a man.”

David rolled his eyes. Sarah took his silence as acquiescence.

About five minutes later, he realized he wasn’t going to get any rest. He decided he might as well enjoy the view and looked out the windshield.

Harlem didn’t look that different from the Lower East Side—perhaps a little less crowded and a little cleaner, but otherwise similar. Light glowed in various windows, and music spilled into the streets from the parties in apartments above. Most of the theaters and speakeasies had closed for the night, leaving the sidewalks barren but for the occasional loiterer or clandestine lovers. David averted his eyes, more to respect their privacy than to avoid recognition. No one here should know who he truly was. He didn’t have to worry about protecting his anonymity—in Harlem, it was a given.

Sarah took a couple turns, eventually backing them into a long, nondescript alley. “This should be it,” she said, head out the window. The rearview mirror was useless—the planks hiding the liquor in the back of the truck blocked the view.

David nodded to acknowledge he heard her, then quickly realized that she couldn’t see him. “Excellent.” He took a deep breath and began to get into character.

Don’t lie about your name or that you’re in the mob , his father had told him. Use your naiveté to your advantage.

He was now David Jacobs, twenty-five-year-old mob novice. His father had gotten hurt doing another (nonexistent, but this proprietor didn’t need to know that) run, and David was taking over his bootleg runs. He tugged at the chain around his neck, checking to make sure that his father’s key was still there. Everything was in order. David allowed an echo of anxiety in—he needed to make sure that his tardiness was as plausible as possible—then opened the door and crept around the side of the truck. He felt around for the edge of the removable panel. Finding it, he pried it off to reveal stacks of cases of scotches and brandies and all sorts of liquor. Rothstein’s European connections certainly paid off.

David pulled out four crates, stacking them. He replaced the panel, picked them up (not too heavy, thankfully—years of mob training had ensured he had more upper body strength than immediately apparent), and carried them slowly towards the back door.

Using the key to get in would be too easy. He needed the runner switch to be apparent. This proprietor needed to trust him if David was to protect this speakeasy for the foreseeable future.

He briefly wondered what this place was actually called. His father had only given him and Sarah an address and curt instructions on the process. David spotted the flowerpot that apparently had a lockbox hidden in it. This was shaping up to be easier than he’d thought.

He set the stack of crates beside him at the door. Knocking would probably be the best move. David checked his watch. Four AM. Shit.

He knocked gently for several seconds, pausing to listen for a response.

Nothing. David knocked slightly harder, then paused again.

He sincerely hoped the third time would be the charm. David was far from defenseless, but he didn’t have the energy for a proper fight tonight.

David knocked for the third time, harder than before.

Whoever was behind the door opened it a crack, shoving a pistol through. David remembered to appear frightened seconds before he caught the slight shine of a pair of eyes behind the gun.

“Who are you?” the man growled. David had to admire his bravery for not dropping his gun, opting to shake like a leaf. “You lost?”

David jumped slightly, pretending to not have noticed the door opening.

The door opened wider, and David was now greeted with a glare from a slim, Black man. This must be the proprietor. “Harlem’s a little far north for ya, pal. Start talking.”

David now remembered that his father had indeed unintentionally dropped the name of this man in his instructions. “You’re Jack, right?” he peeped. Sarah was probably laughing at him if she could hear him. David made a mockery of actors everywhere.

“Who’s askin’?” the man snapped. David briefly went cross-eyed, clocking the pistol aimed right between his eyes. He could read this man—certainly Jack—like a book. David wasn’t going to get shot tonight. He just needed to stay quiet and listen. “This ain’t a good part of town for a white man like yourself. Scram.”

Ah, yes. David still had to state his purpose. That might be important. He translated his quaking physicality into a tremulous tone. “I—I’m Mayer’s son.” That wasn’t a lie. “Here for Rothstein.” Also true. “I got lost.” An unfortunate truth. “First day.” Not technically a lie, but also not quite true. “I, uh. I’ve got your delivery.” One hundred percent true. Lying by omission was one of David’s more disreputable hobbies.

The look of pity on Jack’s face would have made David break down in laughter had he not had that trained out of him years ago. Jack still didn’t lower his pistol, though. Smart. “Bring it in. I can show you the ropes.”

There was nothing for David to do but obey. He leaned down, picking up his stack of crates without so much as a grunt. David could feel Jack’s eyes burning into him.

Jack opened the door, guiding him into a small antechamber. “Don’t let the door slam behind you,” he cautioned softly before leading David down the stairs into the speakeasy. David revoked his previous evaluation—letting him into the actual club was not the brightest move on Jack’s part. Also, he’d lowered his gun in the process of guiding him in. Didn’t he know David could kill him in three seconds if he wanted to?

He didn’t. David’s theatrical skills must have been better than he thought. They descended down another set of stairs, cleverly hidden behind some curtains on the stage, into a storeroom. David’s arms were starting to burn a little.

“You can set them here,” Jack instructed. David set down the crates, making sure his relief was obvious. “Come with me. I got a few questions for you.”

David mutely complied, following Jack back up to a pair of stools on the stage. He had to restrain his amusement. After all, he was putting on quite the show. Jack sat on one of the stools and gestured to the other. David sank down, releasing some of the artificial tension he’d built up.

The look in Jack’s eyes signaled that he may be in for a slight interrogation. Good thing he was prepared. He’d probably only have to tell one or two lies, and his tried-and-true strategy of word vomit was looking like the best tactic for this particular operation.

“First: where’s Mayer?” Jack prodded.

The father question. David knew it was going to come up early on. “He, uh.” David hoped his hesitation would come off as nerves, not lying. “He got hurt on one of his other runs. Asked me to take over.”

He watched Jack contemplate. The excuse sounded rational even to David, who knew that his father was sleeping at home, happy to finally have nights off. It may also have helped that David was the spitting image of a young Mayer Jacobs. Sarah and Les took more after their mother. Jack must be done thinking—he’d adopted a more neutral expression. “Alright, pal. Got a name besides Mayer’s Son?”

David allowed himself to be caught off guard. His cheeks burned (though he wasn’t sure quite how or why that was happening), and he looked down at the floor in a hopefully convincing imitation of bashfulness. “I—I’m David. David Jacobs.” A truth, but not one a novice would admit willingly. “Shit, I’ve already fucked this up. First day in the mob I didn’t know my father was a part of and I’m already bad at it.”

Jack was very clearly overwhelmed. David mentally patted himself on the back for the effectivity of his acting.

“Whoa, whoa, Davey—slow down.” David was not prepared for the way this new nickname sounded coming out of Jack’s mouth. His voice was rough with exhaustion, though still lovely to Davey. David. David may indeed need to slow down. He shouldn’t start carrying a torch for a man he’d just met like a common harlot. “Mouthin’ off like that’ll get you lead poisoning real quick.” This was, indeed, true. David had offed his fair share of talkers. “Real walkin’ mouth you are.”

Davey didn’t like the way his heart had started thumping in his chest. He’d have to play it off as part of this anxious persona he’d assumed. “It’s—Fuck.” David wanted to bite down on the foot he’d just shoved in his mouth. “Pa told me not to argue.” Also not untrue. This had been a part of his undercover training.

“I’ll call you Mouth.” Davey was officially goofy. This was bad. This was very bad. “How’s that?”

Jack’s nickname-giving skills left much to be desired. Davey still nodded, realizing he could cover his tracks with the new name.

“Okay, pal. Mouth,” Jack continued. “Here’s the deal. Your pop knew how to keep this a quick and clean operation.” If only Jack knew just how true that statement was. “You gotta do the same, or you’ll be worse off than him in a matter of minutes.” No shit. “Got it?”

Did Jack seriously think this hadn’t been beaten into his head already? Davey had to remind himself that he didn’t know he was a career mob man and nodded silently.

“You got his key?” Jack asked. “Didn’t know he had a replacement, so I don’t have a copy.”

Davey nodded again, pulling out the chain he’d hidden under the neck of his shirt.

“Good. That unlocks the door you were pounding on so loudly.” Davey had figured, but it was always nice to have confirmation. “Don’t do that again—you’re lucky you didn’t get caught tonight.” Davey knew Rothstein paid off every cop that patrolled the surrounding blocks of this club to keep from raiding it. He’d never get caught. “Unlock the door, drop the booze inside, and hightail it on out. Once you hit Central Park, you’re golden.” Jack had so obviously never left Harlem for any significant amount of time. Even in the dark, Davey knew his way around better. “Don’t wanna be caught dead out here, white boy. Get me?”

Davey couldn’t counter any of this aloud, so he nodded.

Jack was clearly getting frustrated. “I know you got a mouth, boy. Use it.”

Appearing properly intimidated was never a bad idea when it came to characters like this one. “Got it,” Davey mumbled, then paused. There was never a bad time for a stupid question, either. “I should lock the door on the way out, right?”

Jack evidently wanted to slam his own head into a wall. Davey barely kept himself from laughing. “Got no brain in that head of yours, Mouth? You leave it unlocked, we’re all dead, and Rothstein has your head and your father’s.”

Davey cowered, though he knew Rothstein was so very far from ever having his head. He was too valuable. “Um, okay. So. I unlock the door, drop the booze, lock the door, and scram?” Playing dumb was always so much more effective than he thought it would be.

Jack was all business. “Two AM sharp every Sunday.” Like Davey would forget his one delivery time. “Cash’s in the lockbox in the flowerpot. I assume you know who to take it to.” The biggest perk of taking this job was that Rothstein would let him keep the profit instead of his father. “I shouldn’t see hide nor hair of you if you’re doing your job right.”

Odd as it was, Davey was disappointed. He did want to get to know Jack better, though he knew he should keep their relationship strictly professional. Realizing he’d momentarily zoned out, he blushed, nodding. He knew Jack was trying to read him and hoped he was fronting well enough that Jack wouldn’t immediately find him out.

“You’ll get used to it, kid,” Jack added. “Trust me.”

Davey hated condescension, especially from people who held no real authority over him. “Don’t call me kid,” he snapped. “You ain’t that old yourself.” Fuck. He’d need to play extra dumb to cover this mistake. “Also, how’re you gonna know when I drop the booze off?”

Jack’s eyes hardened. “You’ll be on time. The less we see of each other, the better. Capisce?”

Davey blinked, pretending he hadn’t overheard enough conversations with the Italian mafia to know what Jack meant.

“Capisce, y’know?” Jack was really trying.

Davey blinked again. He didn’t like making Jack feel stupid, but he didn’t see another way out of this mess he’d made.

“Damnit, I’ve been around the Italians too much.” So they had an eye on Jack. Davey wondered if the Irish did, too. “Be on time. I should see no trace of you when I check the back at 2:01.”

Now would be an excellent time for Davey’s singular gripe about this job. “So much for a good post-Shabbos sleep,” he grumbled under his breath.

“What was that?” Jack asked innocently. 

Davey wasn’t sure if he’d actually understood him or not, but compliance was never a bad idea, so he held his tongue.

“That’s what I thought.” Davey hoped he’d never have to tell Jack how comical this all felt. “I’ll see your next dropoff next week. Now get outta here before anyone notices you’re gone.”

Davey slid off his stool and raced towards the stairs, then quickly turned back for one last look. He tried to memorize Jack’s face and how at home he appeared here. Jack briefly made eye contact with him. Davey didn’t want to be caught, so he kept going, closing the door behind him and locking it as fast as he could.

He’d taken long enough that Sarah had turned off the truck’s engine. As he slid back into the passenger seat, she started the engine.

“So?” she inquired. “How’d it go?”

Davey sighed. “Not perfectly, but better than I thought. I doubt he knew I was lying.”

Sarah turned, looking him over. “You’re in love.”

Davey grimaced but nodded. 

He wouldn’t allow the sinking feeling he had when he thought about how he’d never see Jack again to consume him.

Chapter Text

Davey’s next few deliveries went by more smoothly—Sarah had practiced the route a few times before their next drive so that they wouldn’t get as lost. Each time he unlocked the speakeasy’s back door, he secretly hoped that Jack would happen to be nearby. 

Davey was disappointed every week.

He had, however, managed to fall into a routine that sped up the process, so at least he minimized the amount of time he was nearest to that aching pull of the tether this Jack had already managed to sink into his heart. Sarah and Kath had started making bets as to how heartsick he’d come back from runs. Sarah usually won, but Davey wouldn’t give her the satisfaction of knowing that.

Davey prepared himself for another uneventful evening as they trundled towards their destination. Stretching as much as he could inside the truck’s cabin, he attempted to loosen up and wake himself up.

“Don’t block my view!” Sarah hissed, batting with one hand at Davey’s arms.

He let his arms go limp, peeking out the side of the truck. Davey loved the smell of the night air. Something about it was invigorating, which was probably helpful considering his particular career path. Soon, he spotted the turn into the alley. It was too hot for his usual uniform of coat and hat, but by this point Davey knew it was unlikely he’d be spotted at all.

Sarah slowly backed into the alley. Davey considered getting into character (as he did every week) but figured that, since it had been three weeks with no sign of Jack, he wouldn’t need to worry about it. Worse came to worst, he was decent enough at improvising his way out of most sticky situations.

Sarah parked, leaving the engine on. “You got this, Mister Big Scary Mob Man,” she whispered, giving him a gentle tap on the head. 

Davey shrugged her off, opening the passenger door and hopping out. Efficiency was his most pressing goal, so he jogged to the back of the truck. While he pried the false end off of the lumber pile, he listened for the music and voices that came from the apartments above. The chatter usually covered any noise he made, and the music was always a nice background to his deliveries. Tonight, he could hear saxophones and trumpets and the odd piano blazing away, battling the night’s heavy darkness. 

He remained lost in thought while he began stacking crates. As he set the third crate on his pile, he heard a small clunk! behind him. 

Without a second thought, Davey whipped out his pistol, aiming it at the source of the sound. Fuck keeping a cover. He needed to keep himself alive. “Don’t make me come find you,” he growled, approaching the sound slowly, gun first. 

Whoever was there wasn’t moving. Davey sincerely hoped it was Jack—that was the only reason he hadn’t just shot at them. However, he needed to get moving. “I’m not going to repeat myself. You got five seconds before you’ve earned yourself lead poisoning.”

Lo and behold, Jack emerged from the shadows, hands in the air. Davey was relieved, though also concerned. Why would Jack be outside the speakeasy at this time of night? He then remembered that, in Jack’s eyes, he was inexperienced and naive. Davey let himself physically relax, mentally keeping himself on alert as he tucked his pistol back into the waistband of his pants. He plastered an easy grin on his face. “Jack! To what do I owe the pleasure?” His volume was measured—loud enough for Jack to hear, but quiet enough that his voice didn’t echo through the alley.

Jack unconsciously shifted his weight from foot to foot. Davey could tell something was up. “We, uh,” Jack began. “We’ve got some negotiations to talk, Mouth. Why don’t you bring those inside?” He gestured to the stack of crates beside Davey. “I can help if you’d like.”

Davey paused, calculating. He was almost certainly walking into some sort of trap. But, he remembered, he couldn’t afford to overthink anything. “I guess I wouldn’t mind some help,” he replied. “Can you take these? I’ve got a few more to get out of the back.”

Jack nodded, then picked up the stack of crates Davey had already set aside. He headed to the back door, propping it open and stepping inside. Davey retrieved four more crates and replaced the false end on the lumber pile.

He picked up the stack, on edge. Something very clearly wasn’t right. Davey reassured himself that his gun was within easy reach and that he could kill nearly any threat (except Sarah). Marching himself towards the door, he could hear the faint noise of a pistol being cocked. Davey quickly made a plan.

Feigning obliviousness, he stepped over the threshold.

Two men—one lanky, tall, and redheaded, the other short and squat with strong Italian features—aimed guns directly at him.

Davey hoped his gasp in mock surprise came off as authentic. To sell the act further, he dropped his entire stack of crates, wincing at the clatter of a bottle shattering in the bottom crate. He pretended these two strange men—probably from the Irish and Italian mob, respectively, if appearances were to be believed—were Rothstein, Pulitzer, and his own father looking at him in disappointment and shook like a leaf.

“I’d put those down if I were you,” Davey threatened. Wait. That was Spot Conlon, one of Costello’s men. Damn it. He was one of the few privy to the knowledge of exactly how dangerous Jack’s operation actually was, and Davey would bet that Costello had weaseled his name out of Rothstein at some point. This was very bad. Davey’s name and face should never have been connected outside of Rothstein’s inner circle. He paled, still shaking, but Spot and his companion obeyed, lowering their guns.

Thankfully, Jack saved the day before Davey had to do any explaining. “So, boys. What’s going on here?” he asked, leaning against the doorframe. “You trying to scare my runner off?”

The redhead squeaked incoherently, and Davey was grateful for all the training he had to hide his amusement.

Spot, however, was not so easily intimidated. “Nice to finally meet the infamous Mouth,” he said, looking Davey up and down. 

Davey felt viscerally uncomfortable and channeled that into his character. He turned to Jack, making sure his slight sense of betrayal was blatantly obvious, layering in some of his falsified fear on top. “Was this the only reason you offered to help?”

Jack opened his mouth, gaping like a fish, then closed it again. He must’ve been caught—Davey knew when it came to mob coercion, there weren’t very many effective defenses. “I—that is, uh—y’know, you people”—he gestured to Spot and his companion—“are really hard to say no to.”

“I see,” Davey replied, placid. That didn’t excuse the fact that Spot Conlon, of all people, had managed to confront him, but Davey knew the fear of God a man like that could put into his victims.

An awkward silence settled in—Spot clearly wanted to say something, but, when Jack wasn’t looking, Davey shot him a glare that he hoped was intimidating.

After a few moments, Spot’s compatriot took him by the arm. “We’ll, uh. We’ll be going now. See you later, Jacky-boy,” he said, quickly pulling Spot deeper into the club, probably to a hidden raid exit. Jacky-boy! Davey wanted to laugh. What a nickname. He’d thought Jack had been bad, but these two were so much worse.

Davey returned his attention to Jack, who gestured at his stack of crates. “Why don’t I, uh. Take care of that for you. There’s a wet rag on the bar if you could take a moment to mop that up.”

Now that Davey was fairly certain he was alone with Jack, he didn’t want to leave, so he obliged, setting to work on the spill. He took his time, almost worshiping the task.

Finally, he could faintly hear Jack humming a tune, getting louder as he approached. Davey stood up, turning to the door out to pretend he didn’t hear. Jack stepped into the room. Davey hesitated. Kath was going to win the bet tonight—he hadn’t known Jack could sing . “That’s a nice tune,” he said, trying desperately to hide his feelings. “See you around.”

With that, he swiftly climbed the stairs out, shutting and locking the door behind him. Sarah had turned the truck’s engine off while she waited, and she revved it as he slid back into the passenger seat.

She got right to the point. “What took you so long?”

“Irish and Italian guys pressured Jack into cornering me.” Davey figured concision was his friend.

Sarah slammed on the brakes. “Who?”

Davey recovered from his brief whiplash. “Didn’t know the Irish guy, but Spot Conlon was there.”

“He’s with Costello now, ain’t he?” Sarah floored the accelerator.

“As of late, I believe. Seemed like he put two and two together. Don’t like how he knows my real name now.”

“You gotta be more careful, palant ,” she warned. “Soon the entire city’ll know who you are.”

Davey didn’t burst often, but Sarah had a tendency to know exactly how to set him off. “You think I don’t know that? The fact that my security rests on whether Spot fucking Conlon keeps his goddamn trap shut gives me hives! Fucking hell, Bear. Leave me alone.”

“I’m just—”

Davey stuck his fingers in his ears like a child, pouting, and turned away from her.

She huffed and kept her eyes on the road. The truck’s cabin was silent the whole drive back to the Lower East Side.

Sarah pulled into the alley behind Rothstein’s warehouse, checking their surroundings before turning off the engine. “Come over.” There was no room for negotiation.

“Fine,” Davey whined dramatically. To be fair, her apartment was closer to the warehouse than his, but spending the night at hers meant having to deal with Kath, too. The issue wasn’t that he didn’t like Kath—quite the opposite, in fact—but that she and Sarah together were a force to be reckoned with, and he was rather exhausted.

Still, Davey begrudgingly obliged, playing the part of a responsible adult as they quickly made their way to the back door of her building and silently raced up the stairs. They were becoming well-practiced with this maneuver, as much as he was loath to admit it. Sarah’s apartment was just easier to crash in than Davey’s.

Sarah got to the door of apartment 5B first, slipping through it sideways. Davey followed and shut and locked it behind him.

“Welcome back,” Kath said, taking a drag off her cigarette. She sat on a sofa facing away from the door, and Sarah immediately collapsed on top of her. Davey couldn’t see her face, but Kath’s head tipped downwards towards Sarah. “Rough night?”

“Yeah,” Sarah acquiesced. “But we still have business to attend to. David?”

Davey sighed and flopped on the couch opposite them, swooning mockingly. “I caught a glimpse of his shimmering eyes and well-kept mustache and I surrendered my heart to him! I only wonder how long I’ll carry this torch—”

“We get it, Shakespeare.” Sarah tapped Kath’s nose. “You win, for once.”

A slow smile spread across Kath’s face. “Excellent. May I claim my prize?”

Davey groaned. “Get a room.”

“That was the plan until someone dragged you here,” she shot back.

Sarah made her trademark puppy-dog-eyes, and Kath softened. “Not that I’m not happy to see you, David.”

Davey rolled his eyes. “Sure.”

“You saw him tonight.” Kath’s tone was all business. “That’s unusual. Did something happen?”

Davey clutched a throw pillow to his face, trying not to scream.

“All I got out of David here was that Spot Conlon saw him and put two and two together,” Sarah said.

Kath paled. “Spot Conlon?”

Davey sat up, setting the throw pillow on his lap. “Spot Conlon, my former paramour, the king of Brooklyn, my worst teenage mistake—call him what you will.”

“Seems he’s gotten involved with Costello,” Sarah helpfully added.

“He didn’t know of your… involvement, did he?” Kath asked.

“Spot knew me as David Jakobwicz, a Polish-American perfectly average teenager. I doubt he knew anything was amiss, since I claimed to be busy with homework whenever Aba needed me for another job.”

“So this is a problem.” Kath seemed to have decided to give the understatement of the year.

“What, the fact that I’m now running deliveries to the most dangerous speakeasy in the city and have just been discovered by my schoolyard boyfriend who is now a member of the fucking mafia and in cahoots with the Irish mob? Couldn’t be that.” Davey was stretched thin. Exhausted, stressed, and sick of being reminded of his failures by his sister and her girlfriend, he opted for the guest room, where he could hopefully fall into the bed that was unofficially-officially his in the wee hours of Sunday mornings. 

“Wait!” Kath exclaimed, stopping Davey in his tracks. “We do need to plan some sort of intervention.”

Davey made a whining noise like a kicked puppy. “Can’t you do that? I’m tired.”

“Fine, fine,” she replied, waving him off. “But you’ll have to go along with my plan.”

Most of Davey’s job to begin with was following orders, and he reminded Kath of that.

“Fair. But you have to tell Rothstein.”

Shit. Davey did not want to tell Rothstein.

Sarah saw the fear in his eyes. “Or you could tell Aba, who’ll tell Rothstein for you.”

“Can’t I just go put the fear of God in Spot or something? I feel like that’d be easier and keep you from losing a brother.”

“David,” Kath interjected, suddenly much darker. “You’re much too valuable to my father for Rothstein to kill you.”

Davey returned to his sofa, flopping back down with a grunt. He couldn’t walk out of this conversation now. “Damn.”

“You should at least tell Aba.” Sarah reached over and poked at Davey’s side. “He’ll know what to do.”

“Kath…” Davey sighed. “We’re going to have to accelerate things, won’t we?”

“Twenty-six is on the older side of maidenhood,” Kath replied, picking at her nails. “Besides, we did know we’d have to do it eventually. It might make our living situation easier, too.” She tapped at Sarah’s nose.

Davey rubbed at his eyes with the heels of his hands. “Guess I’ll go ring shopping, then. Got any requests?”

“Not particularly. It better be expensive, though.”

“Why did I expect anything more?” Davey rolled his eyes. “I’ll see what I can do.”

“Thank you, honey,” she said, overtly batting her eyelashes. “Til death do we part, and all that bullshit.”

“Of course, sweetheart,” he responded in the same facetious tone. “I’m ready for your ball and chain.”

Sarah huffed indignantly.

“At least you have an option out,” Davey shot back. “I’m stuck with this one for life.”

“Or until Rothstein and my father are dead,” Kath added.

Sarah abruptly sat up. “Let’s not think about that.”

“Am I… free to go now? I’m so tired,” Davey whined.

“Sure,” Kath said, shooing him towards the guest bedroom.

Davey enthusiastically obliged, planning to dive bomb the soft queen bed. He couldn’t indulge in his youth often, so he compensated by being especially childish around Kath and Sarah.

He landed ungracefully, limbs flying everywhere. The duvet was heavenly . Davey needed to ask them where they got it—his own bed was not nearly as comfortable. As he (reluctantly) got up to close the door, he could somewhat make out the sound of conversation. He closed the door silently, then leaned against it to eavesdrop.

Sure, Kath and Sarah probably wouldn’t appreciate his listening in, but they had to know by now that Davey would do anything to obtain extra information.

“…I think I should go check in, at least,” Kath was saying.

“I don’t know,” Sarah replied. “It’s far, and you’d be alone…”

“Don’t you trust me? I may not have been raised with quite the degree of training you had, but I’m no dumb Dora. Besides, you know I’ve done lots of intelligence work.” This was obviously a battle Kath intended on winning. Perhaps she could figure out if Jack would be at all romantically inclined towards him. Not that that would be central to her self-imposed mission, but it would be nice to know so Davey could figure out whether to attempt to put out that torch he’d lit.

Oh. Perhaps she could figure out a way to distract Jack for a night so Davey could take care of Spot and his companion. She and Sarah did have those parties… but how could they justify inviting a strange Black man?

Maybe Jack could sing for them. Davey felt dirty for even having to think of excuses to get Jack in the room. But he had, to be fair, learned that Jack had quite the musical skill.

Davey’d gotten so wrapped up in his far-fetched ideas that he’d zoned out momentarily. He pressed his ear back to the door, hoping he hadn’t missed out on too much.

“...No, Bear, I won’t tell him.”

Sarah murmured something in response, but he couldn’t catch it. Perhaps that was for the best. Was Kath implying that there was something she wouldn’t tell Davey? Or was this “him” someone else? Now that Davey thought about it, she most likely was referring to her father. But he wasn’t the only person she could keep in the dark.

Davey’s sleep-deprived brain could not continue to process all these questions. Whatever Kath was planning, he’d eventually be looped in on it. Or so he hoped. She was often better at keeping secrets than he gave her credit for. They were playful and childish around each other to cope with the fact that they’d soon be forced into marriage, so Davey often forgot how intimidating she could be.

Satisfied, he quickly prepared for bed, sinking into the satin sheets. As he drifted off, the echoes of a gentle tune and the glimmer of a dark pair of eyes crossed his mind, soothing him into sleep.

Chapter Text

Davey usually loved visiting for Shabbos with Sarah, but approaching the front door of his childhood home alone on a Monday afternoon was daunting. He knew his parents loved to see him, and Les never hesitated to pepper him with questions about his latest exploits. The weight of Spot’s knowledge sat heavy on his shoulders; the resistance pulled his fist away from the door before his knuckles had touched it once.

He knew he looked like an idiot. The curious stares and annoyed glares from several passersby in the hallway in front of his parents’ apartment had shown him as much. How hard was it to knock on a door?

Just as he’d worked up the courage to knock, the door swung open. Davey tumbled into the apartment, tugged by the shirtsleeve. By the time he’d regained his bearings, he had collapsed into an armchair, Les staring down at him.

“Nice to see you again, palooka,” Davey prodded. He never gave up an opportunity to give his younger brother a hard time.

Les, predictably enough, scoffed indignantly. “Was wondering when we’d see you around here.”

Davey casually crossed one leg over the other. “What can I say? I’m a busy man.” He could tell that Les was having a hard time restraining himself from questions and smirked. “Lots of secret business I’ve got to take care of.” Perhaps that “secret business” was figuring out how to romance a bartender from Harlem, but Les didn’t need to know that.

Heavier, socked footsteps thudded from the back of the apartment. Davey went on guard, though his casual posture wouldn’t show it.

“Aba’s missed you,” Les said, settling into another armchair and inspecting his nails. At seventeen, he’d started to pick up some of their father’s mannerisms in an attempt to appear more grown-up. Davey didn’t have the heart to tell him that this wasn’t exactly the behavior of on-the-job mob men.

“Dawidek!” 

Davey looked up into his father’s eyes.

A warm smile stretched across Mayer’s lined face, though Davey could spy a hint of worry behind it. “What brings you here?”

Davey glanced at Les, then back to Mayer. “Figured it’d been too long since I last visited for anything besides Shabbos.” He still wasn’t sure how much information Les had on his current occupation as an undercover bootlegger.

“Lesław, why don’t you go get your brother and myself something to drink?” Mayer directed.

Les protested. “But—”

“Now, Lesław.” He gave Les the look that Davey remembered so well from his early days of training: obey, or else.

Les scurried off to the kitchen, loudly opening and closing cabinets. Davey took his head in his hands.

“Dawid ? Dawidek, look at me,” Mayer instructed.

Davey peeked through his fingers.

“What’s wrong, son?”

“Who said anything’s wrong?” Davey asked, trying to play off his nerves. “Can’t a fella surprise his pa every once in a while?”

“When was the last time you visited outside of Shabbos?”

Davey had to think for a minute, counting on his fingers. “Uh. Passover?”

“Passover!” Mayer exclaimed, throwing his hands in the air. “Uh. Passover?’ he says! My eldest son hasn’t visited home since Passover! That was April! It’s August, Dawid!”

Davey deflated a little, cowed. In the meantime, the kitchen had become suspiciously silent. Glancing in the direction Les had gone, he quietly changed the subject. “Has Les joined the family business?”

Les, miraculously enough, had chosen this opportunity to return, two mugs in his hands. “Have I what? Also, here’s your oranżada,” he said, handing the mugs to Davey and their father.

Mayer tipped his head in thanks, then returned his focus to his elder son. “Not in your particular capacity, but he’s yet to take on any real work.”

“But he knows?” Davey pressed, earning a quizzical look from Les.

“Some,” Mayer acquiesced. “Enough to get by, should need be.”

A plan began to fall into place in Davey’s mind. “And if I were, hypothetically, in a bit of a bind… would he be in a position to, say, lend his big brother a hand or two?”

Les’s eyes went wide. “What—”

“Lesław, my boy! I can’t believe I’ve forgotten—we were supposed to borrow some sugar from the Gliksmans. Can you go get it?” Davey knew this was one of Mayer’s classic diversion tactics—the Gliksmans’ son Henry was one of Davey’s few childhood friends and frequently helped him on the job.

Les hung his head, disappointed. “Yes, Aba.” He raced out of the apartment, slamming the front door shut behind him.

“What’s going on, son?” Mayer gave Davey a gentle, fatherly smile. “You need my help with something?”

Davey scratched the back of his neck. “I… uh… yes. It’s, um. It’s about the job.”

Mayer, confused, thought for a moment. Recognition dawned on his face. “Ah, yes. The job. How’s Harlem treating you?”

“Quite well, actually,” Davey replied. “But…”

“But what?” Mayer prompted.

“But… the Irish and Italian watchmen pressured Jack into cornering me. Don’t think the Irish guy had any idea who I was, but…” Davey didn’t want to keep going.

Mayer’s eyes bored into him. 

Davey sighed. “You remember Spot Conlon?” He couldn’t bear to look at his father.

Mayer hummed for a moment, thinking. “Little Italian kid? You knew him from… I don’t remember. He came around here once or twice, right?”

“He ain’t a kid anymore, but otherwise yes. Got himself aligned with Costello, of all people. He was there. Pretty sure he put some pieces together that he shouldn’t have.”

“That’s quite the situation, son.” Davey couldn’t place Mayer’s placid tone. After a long silence, he continued. “What are you going to do about it?”

Davey froze. “What am I going to do about it?”

Mayer nodded sagely. “What are you going to do about it? I am retired. This is your job now. What are you going to do?”

Davey paused, allowing his thoughts to coalesce into a plan. “I’ll… take care of him. Bring some boys up with me to the club, catch him there. I’ll stay out of sight while they... stress the importance of keeping secrets. Could I bring Les along?”

An approving smile spread on Mayer’s face. “I can barely control him as it is. He’s yours for the taking.”

Les was never going to be able to thank Davey enough for this.

Right on cue, the front door slammed open and Les skidded in, a small jar of sugar clenched in a fist. “Wha’s hap’nin’?” he asked around the cookie still stuck in his mouth.

Davey grinned. “I’ve got a job for you.”

Davey lounged in his armchair, paging through his well-worn copy of Howards End. Yawning, he stretched, setting the book gently in his lap, then checked his watch. Midnight—too early for sleep. He returned to the novel as Henry proposed to Margaret, devouring the same scene he’d read a thousand times as if he’d never seen it before. Davey didn’t often have time to himself, so he enjoyed taking the few moments of solitude he had to remind himself of art, beauty, love, and pain. He didn’t know quite why he felt such a strong tie to this particular book: perhaps it was the importance E.M. Forster placed on finding and establishing a home and family, or perhaps it was his particular narrative voice.

The phone rang, interrupting Davey’s ruminations. He sighed, carefully marking his place with the special ribbon he used only for this book, and pushed himself up, meandering over to his candlestick telephone. Taking the transmitter in his right hand and the ear phone in his left, he sat at his desk. “Hello?”

“David?” Of course it was Sarah. No one else called him at this hour unless he was on a job. And, even if someone were calling him about the deliveries, it’d be Sarah anyway.

“Bear, what’s going on? It’s rather late.” Davey yawned loudly into the mouthpiece.

“I’m bored.”

“That’s what you have Kath for, isn’t it?”

“Kath’s… not here at the moment,” Sarah replied after a brief hesitation.

“When will she be back?” Davey didn’t want to leave the comfort of his apartment, especially at this time of night.

“I don’t know. Probably late. Please come over? You can stay the night if you’d like.”

“What’s in it for me?” He knew she had to have something up her sleeve.

“I’ve got a tasty bowl of raspberries here and you’ll be sorry to miss out on them.”

Damn. Raspberries sure would be worth the short hike to her apartment. Davey’s icebox didn’t work particularly well, and Kath and Sarah had recently obtained a real refrigerator. “Fine,” he relented. “But no funny business, you hear?”

Sarah giggled. “See you soon.”

The line went dead, and Davey gratefully hung the ear phone back up on its stand. Standing up, he rolled his shoulders, searching for anything he might need to bring with him. Keys—stashed in a pocket. Book—he could live without it for the night, so he tenderly slid it back into its place of honor on his small bookshelf. Though it was fairly warm, he still slid his shirt and vest back on, quickly buttoning up the fronts, then threw his lightest coat over. Oh—and he couldn’t forget his hat. Blindly, he snagged one off his coat rack, hoping it would at least somewhat match the rest of his outfit. He laced up his shoes, opting to forego his spats for the sake of efficiency, and wearily trudged out the front door of his apartment, locking it behind him. 

Thankfully, it was only a few blocks to Kath and Sarah’s place. Davey darted through the familiar back alleys and hidden pathways, avoiding as many main streets as possible. By this point, he’d memorized every possible path between their apartments, careful not to repeat the same one too frequently.

Having reached their apartment building, he pressed the buzzer. The front door almost instantly clicked open, and he raced up the stairs. Davey took pride in his athletic capabilities: despite having practically sprinted up five flights of stairs, he hadn’t broken a sweat and was only barely breathing harder.

He tapped lightly at the door to Kath and Sarah’s apartment, then let himself in, shut the door behind himself, and hung his hat on the coat rack. Oh. That was the hat he’d chosen. At least it was dark out—Davey prepared himself for the shame of wearing a mismatched hat with his coat the next morning.

Sarah lounged on the couch facing the door, eating raspberries off her fingertips. “Was wondering when you’d get here,” she said through a mouthful of fruit. “How are you?”

“I’m fine,” Davey replied, settling on the couch opposite her. “Bit tired.” He paused. “Hand over the berries, will you?”

Sarah replaced the raspberries she’d eaten on her fingertips, then passed him the bowl. “How’s Aba?”

He groaned. “Upset that I don’t visit more.”

She raised an eyebrow.

“Pretty much told me to solve the problem myself. Les is coming with.”

Sarah’s eyes went wide. “You didn’t.”

Davey popped a raspberry in his mouth. “I sure did.”

“Kid’ll owe you for life.”

“That’s the plan.”

Sarah took a deep breath. “Isn’t that a little cruel?”

“You should really know by now that that’s just how life in the mob works. And hey—it’ll keep me in his good books for a good while. One more person I know I can trust. That list is getting shorter by the day, somehow.”

She opened her mouth to protest right as the front door swung open.

“Honey, I’m home!” Kath whisper-shouted. After closing the door, she swung her arms wide. “Come give mama a little sugar.”

Sarah grimaced a little, nodding her head towards Davey.

“Oh!” Kath exclaimed. She took a moment to collect herself and hung her coat and hat on the rack by the door. “No rule that you can’t give me a kiss while he’s around, anyway.”

Sarah ate another raspberry off her index finger. “Don’t wanna get up,” she grumbled.

“That’s no problem at all,” Kath said, settling beside Sarah, who only lifted her head long enough to rest it in her lap. Pressing a delicate kiss to her forehead, Kath began to absentmindedly stroke Sarah’s hair.

Sarah purred softly.

“Gross,” Davey grimaced.

Kath took a deep breath.

Davey tensed.

“I paid him a visit.” Kath’s gaze bored into his head.

“Who?” Normally, Davey could somewhat pick up on Kath’s vague statements, but he was too exhausted to think tonight.

“Your man.” 

Sarah cackled gleefully.

Davey’s hackles rose. “You didn’t.”

“I sure did.” She giggled, ruining any sultry effect she’d been going for with that red lipstick she was so fond of.

“Kath, I can take care of my own business,” he protested.

“Are you sure about that? You seem to be stuck in a bit of a bind at the moment.”

Davey didn’t like when Kath was right. “What did you do?”

“Turns out your fella has quite the set of pipes.”

Davey blinked. “What?”

“You didn’t tell me this Jack of yours was a singer. And quite a good one at that.”

Davey couldn’t follow. “He’s just the bartender—though I did hear him hum something nice once.”

“Oh, and he did pour me quite the drink. Lit it on fire and everything.”

He couldn’t tell if Kath was being serious.

Sarah tapped Kath’s nose. “Is Jack trying to steal you away from me?”

“No, darling,” Kath replied, “I’m yours for good.”

Davey made a gagging noise.

“Oh, get off your high horse,” Sarah admonished. “We have to listen to you pining all day—let us be sickening in peace.”

“Fine, fine.” He paused. “How’d you end up hearing Jack sing?”

“He said something about doing a favor for the owner—couldn’t get more out of him than that,” said Kath.

“Interesting.” Davey mentally kicked himself for missing out on Jack’s performance.

“Oh, and I invited him over next Sunday,” she added.

“You… invited him to your salon?” Davey parroted back.

“I did indeed. I thought my little canary here”—Kath tapped Sarah’s nose—“could use a new duet partner.”
There was something dangerous hidden underneath her light tone. Davey picked up on what she was implying.

“And I could use some time to take care of the Irishman and the Italian.”

“Indeed.” Kath’s glittering, sharp-toothed smile returned. “You’re welcome.”

Davey mentally took roll again. Les had, remarkably enough, managed to not get lost on the longest subway trip he’d ever taken. Henry Gliksman was there, standing resolutely beside Bill and Darcy, Kath’s old friends. Perfect. 

He glanced across the 57th Street subway stop again, making sure they weren’t being watched.

Was that Jack in a swanky blue jacket heading south?

Not wanting to waste any more time, Davey waved his men (and boy) along subtly, and they quickly ascended the stairs to the El, which they’d take the rest of the way to Jack’s speakeasy. Hopefully, Spot and his companion would be there tonight.

Davey’s mind wandered as the El trundled up towards Harlem, wondering what Jack was doing at Kath and Sarah’s—if their usual guests had welcomed him, and what he was performing.

Les kicked at Davey’s ankle. “I think we’re almost there.”

Davey tuned in to the garbled announcement from the conductor to confirm. “So we are.” He nodded to the other men with them. “Ready?”

Darcy and Bill nodded, and Henry gave him a subtle thumbs up. This wasn’t their first rodeo.

Davey slunk off the train, not checking to see if his entourage followed. The plan was simple: he’d keep watch, since Spot and his companion knew who he was. Darcy, Bill, Henry, and Les, in the meantime, would work together to encourage Spot to forget about Davey. If that message happened to be shared with his mysterious companion, so much the better.

Davey kept his head down as he casually meandered towards Miss Medda’s and the fire escape on the back of the building. The neighboring apartments, again full of light and life, allowed him to slip through the back alley unnoticed. He scrambled up the fire escape as quietly as possible, then found a good spot to perch on top of the building, watching both the alley behind and the street in front of it for any signs of trouble.

Les and Henry slipped into the building next door, planning on using one of the escape routes in. Davey watched as Darcy and Bill entered through the front door. Hopefully, Spot would already be inside. 

Davey tensed, on guard. Everything seemed to be going to plan. Or, as much of the plan as he knew. It was always safer for everyone to have plausible deniability—he’d simply asked his men to make sure Spot (and, perhaps, his companion) wouldn’t go looking where he shouldn’t. 

Five minutes passed agonizingly slowly. Davey, ensconced in shadows, crouched perfectly still, all impulse to fidget trained out of himself long ago. He longed for distraction but kept his focus: this was supposed to be a quick, one-and-done job, after all.

Several minutes ticked away on Davey’s pocket watch. His fingers itched to do something—he wasn’t used to feeling quite so useless. Typically, he’d be closer to the action, but he’d blundered his way into this mess (well, Jack had, but that was beside the point. This was Davey’s problem now.) and couldn’t rescue himself for once.

Why did Costello have to pick Spot Conlon in particular to keep an eye on this joint? He had to have other cronies. A little speakeasy in Harlem didn’t seem to be Spot’s typical scene, but, then again, who was Davey to judge? Miss Medda’s was by far the riskiest establishment around. Of course the Italians needed good eyes on it.

A few more minutes passed. Davey watched a basement door on the building next door swing open as two figures scampered out. One was too short and squat to be anyone he’d brought with him—this must be Spot and his companion, thoroughly convinced, escaping the scene. Perfect. Davey peeked over the opposite side of Miss Medda’s—there, indeed, were Les and Henry, stationed outside. Bill and Darcy would stick around the club for a while longer to avert suspicion. Davey would stay longest of all to make sure everyone made a clean escape (and to make sure Jack got back safely, though he didn’t mention that when they were planning the job).

An hour passed. Davey had watched Darcy and Bill jovially exit the club with several friends they’d made, and, one by one, the lights had begun to turn off in neighboring buildings. A muffled saxophone crooned, melancholic, as a silhouette, illuminated by moonlight, staggered into the alley. The hairs on Davey’s neck stood on end.

As Jack (still in his recognizable outfit from earlier) approached, Davey realized that he wasn’t hurt—just very, very tired. A night at one of Kath and Sarah’s parties could certainly do that to a man. Davey watched to make sure he got in the back door, then decided to call it a night. Jack was safe, his men were ostensibly safe, and Davey was now safe from Spot.

Davey leafed through Howards End for the fifth time that Thursday, but nothing stuck out enough for him to reread. He groaned, disentangling himself from his armchair. It was time to peruse his (rather meager) bookshelf for another option. Conveniently, as he slid Howards End back into its place of honor, his phone rang.

“Hello?”

“Greetings from Sarah Jacobs’s Fun Factory,” Sarah’s voice crackled over the phone.

Davey rolled his eyes.

“I can hear you rolling your eyes. Tell me you had fun plans for tonight and I’ll leave you alone.”

“I…”

“Please tell me you’ve at least picked up a different book.”

Davey chose not to respond.

Sarah sighed loudly. “Come and see Jack sing tonight, David. He’s quite lovely.”

“So Kath’s article said,” he replied. “What’s in it for me?”

“A night not spent bored off your ass? Come on. It’ll be fun and you can claim it’s work related.”

Mentally, Davey had already relented, but he didn’t want to give Sarah the satisfaction of knowing that. “Perhaps I like being bored off my ass.”

“No, you don’t, głupek. I’ll be at your place in fifteen minutes. Be ready.”

Davey heard the line go dead as she hung up. He set the ear phone back on the transmitter and then took a deep breath. What would he wear? Davey didn’t want to dress too obviously like he was in the mob, but he also didn’t want to stand out too much.

He wandered over to his wardrobe and sifted through the various jackets, coats, and shirts that he’d managed to collect throughout his years of high-level defense and infiltration. Ah. There it was. His sleek black tuxedo, a bit dusty from disuse. Davey grabbed the matching shirt and pants and dug through drawers to find his cummerbund and bowtie. Perfect. He threw them on and rushed out of his bedroom back to his small parlor.

A light knock tapped at his door.

“Come in!” Davey called, tying a shoe.

The door creaked as Sarah waltzed in, all glitz and glamor under her long coat. “Ready to go?” she asked.

“Calm down, Bear. You gave me fifteen minutes to get ready—let me get my coat and hat, then I’ll be good to go.”

Sarah mock-tipped her hat at him. “Of course.”

Finally fully dressed in coat and hat, Davey nodded towards the door. Sarah clapped in joy, tugging him out. He locked the door behind them before continuing to the El, arm in arm with his sister.

Entering Miss Medda’s from the front was a rather strange experience for Davey. He hadn’t seen the club in operation before, and the combination of smoke, glitter, and constant movement was disorienting. 

Sarah grinned beside him. “Isn’t it the tiger’s spots?”

Davey allowed himself a moment of slack-jawed awe. “That’s certainly one way to put it.”

The crowd’s chatter was nearly overwhelming.

“Why don’t you get us some drinks?” Sarah shouted over the hubbub. “I’ll find us some seats.”

As Davey approached the bar, he noticed that everyone patronizing the place was white. Oh, right. This was another of Rothstein’s stipulations for leniency. Waving over a bespectacled bartender, he ordered a sidecar for himself and a Mary Pickford for Sarah. Davey scanned over the club while he waited for the bartender to mix the drinks. He recognized some faces from Sarah and Kath’s parties—it seemed that Kath’s article had made Jack rather popular all of a sudden. Eyeing the tables near the tiny stage where the band was tuning up, Davey searched for Sarah. Why on earth had she chosen a table in the front row? Davey supposed she did quite enjoy schadenfreude, particularly when it was his pain involved. He wasn’t sure how he’d react to being so close to Jack so publicly, but he supposed he’d find out soon enough.

“Here you are, sir,” the bartender interrupted Davey’s thoughts, pushing two mugs over the bar.

“Thanks,” Davey answered, passing him more than enough cash to cover the drinks. “Keep the change.”

The bartender smiled slyly, sliding one of the extra bills into a vest pocket.

Davey approached Sarah’s table cautiously, taking care to ensure he didn’t spill the drinks. Setting them down gently, he peeled off his trench coat and suit jacket, which had become stifling in the hot air of the club.

Sarah sipped at her drink. “He’ll be on soon,” she said, answering his unasked question.

Davey stared into his mug to avoid responding.

“You really missed out at our party last weekend,” she continued. “Shame you had to miss it.”

“You know I had business,” he replied curtly.

Suddenly, the band began a bright, familiar vamp. Davey started. Sarah chuckled quietly beside him; he elbowed her in frustration.

Jack stepped out, resplendent in a blue jacket. Davey couldn’t tear his eyes away from the stage. He wondered how long it’d take Jack to notice him.

“Hello, hello!” Jack greeted over the music. Davey was going to pass out. Normally, he could keep his cool in nearly any situation, but Jack was a particular weakness he had a hunch he’d never overcome. “Welcome to Miss Medda’s. I, obviously, am not Miss Medda—she’ll be on once you’ve had your fill of me. I’m Jack the Singing Bartender, and I’ll be your opener tonight!”

The crowd went wild. Davey was totally out of his element.

“You’re the cream in my coffee; you’re the salt in my stew…” Jack began.

Just then, Jack caught Davey’s eye. Several emotions passed quickly over Jack’s face as he recognized Davey.

Davey noted how Jack glanced quickly back and forth between himself and Sarah. How had Jack not connected the dots before?

He applauded Jack for his ability to continue performing while clearly having an emotional revelation, almost getting lost in his analysis of the situation enough to miss the next line of the song Jack had been humming the day they first met.

“You will always be my necessity: I’d be lost without you.”

Chapter Text

Davey sat in shock through the rest of Jack’s set. He was an enthralling performer, and Davey wanted to melt into the music. He could feel Sarah’s self-satisfied smirk the whole time, but he couldn’t bring himself to care. Jack crooned through a set of ballads that had Davey letting his guard down little by little like the amateur he was pretending to be. 

Before Davey knew it, the band had stopped playing. “Thank you all!” Jack shouted over riotous applause. “I’ve been Jack the Singing Bartender, so I’m off to the gin mill until tomorrow night. Now, enjoy the real star of the show—Miss Medda!” With that, Jack left the stage as the speakeasy’s namesake entered. 

Sarah poked his shoulder, and only his well-honed mob instincts kept him from jumping out of his seat. “Miss Medda is excellent, but why don’t we scram and catch your fella out back? Don’t want to be seen here for too long or Aba’ll be unhappy with us.”

Davey pretended to contemplate Sarah’s proposal for longer than necessary until she handed him his coat and hat and shepherded him out the front door. Once they were both bundled back up, she put her arm in his long enough to steer him around the block and towards the alley behind Miss Medda’s. Davey started to sweat, and he wasn’t sure if it was nerves he hadn’t felt since he was a teenager or the warmth of the night.

Regardless, they fell into their usual step, walking just loudly enough to make their presence known but not so loudly that it was obviously intentional. Davey peeked out from under the brim of his fedora. Smoke curled up into the night air from a dark figure in a starched white shirt—it had to be Jack—until he froze, stubbed his cigarette out, and started patting all of his pockets like some rube who’d just come to the big city for the first time. Jack started to look up, and Davey had to hide his schoolboy grin in the shadows.

Sarah’s presence at his side urged him forward. In a matter of moments, they stood before a cowering Jack Kelly.

“Hello, Jack,” she gushed as Jack visibly relaxed. “That performance was the duck’s quack. We should really come out here more often to see you!”

It was only Davey’s well-honed instincts that kept him from jumping. Sarah’s elbow caught him in just the right spot to make him wheeze. “Take off your hat, bałwan,” she hissed into his ear.

Wordlessly, Davey removed his hat.

Jack made a noise that Davey could not process.

“Jack, meet my brother David. He’s had to hear me blabber on about singing with you all week, so I figured I’d show him what I was talking about. David, this is Jack,” Sarah interjected to fill the silence. 

Davey watched Jack process Sarah’s cover. When he wasn’t performing, Jack seemed to think in a way that was immediately visible on his face.

Davey spent so long focused on parsing Jack’s expressions that he briefly missed his outstretched hand, which he shook with the grip he used to scare the living daylights out of his own men. Hopefully it’d hide Sarah’s involvement with their family’s more unsavory dealings. “Nice to meet you, Jack,” he said, hoping Sarah wasn’t choking back a laugh beside him. Davey schooled his expression into something resembling the nerves of a first-time bootlegger.

“My pleasure, David,” Jack replied, shooting a metaphorical bullet through Davey’s heart. He hadn’t realized quite how much he’d come to treasure Jack’s nickname for him.

Davey could feel Sarah’s eyes on him but couldn’t bring himself to care. “I’m trying to convince David here to come to the party this week, but he always says he’s too busy or tired,” she piped up. “I thought you might be helpful with that.”

Davey wanted to kick her.

A grin spread across Jack’s face. “C’mon, Mac. I can show you how to have a good time if you show up.”

Davey let himself blush in the name of keeping his cover, then sighed. “Guess I’ll have to find out somehow, since I seem to be Mr. Has No Fun.” 

Jack and Sarah cheered quietly at his expense.

“We’ll see you Sunday, Jack. Remember: same time, same place,” Sarah said, taking Davey by the arm. She replaced her hat; he quickly followed suit as she escorted him down the alley.

Jack faintly wished them a farewell.

Davey could sense they were being watched as they walked, so he relaxed into his usual vaguely intimidating stride as best he could.

“The hell was that for?” he hissed after they’d turned the corner.

“You’ve missed far too many of our parties of late,” Sarah replied innocently. “Besides, I thought you liked him.”

“That’s not the issue,” Davey grumbled as they made their way towards the El.

That Saturday, Davey had just finished loading Rothstein’s latest imports into the truck he and Sarah took up to Miss Medda’s when he heard a steady, familiar gait approaching. “Mr. Pulitzer,” he greeted without turning around.

“David,” József Pulitzer answered. 

Davey could hear the false smile in his tone, so he jumped down from the back of the truck and turned to offer his hand. Pulitzer took it and shook it firmly.

“What brings you here tonight, sir?” Davey asked. Typically Sarah was his only company this late at night, but she usually arrived shortly before they needed to leave. Often, Davey loaded the truck alone.

“Can a man not visit his future son-in-law without an agenda?” Pulitzer said with a brittle laugh.

Davey gritted his teeth. “Right, yes, of course, sir.”

“How are you and my daughter these days? I haven’t seen you much as of late,” Pulitzer probed.

Davey did not like the direction this conversation was going. “I have seen Katherine when I could, sir, but this new assignment has kept me busy.”

Pulitzer hummed thoughtfully. “I fear your time apart these last few months has started encouraging her towards… ill-advised pursuits. She’s taken to writing, which would be tolerable if she didn’t insist on publishing so much of it. And word on the street is she was spotted socializing with unsuitable men.”

Davey nodded gravely. “I see, sir.” Kath’s trip to Miss Medda’s seemed to be endangering them both.

“Excellent,” Pulitzer said, reaching into a pocket of his summer coat. “You’re a clever young man—it’s high time you settled down, anyway. I’m glad we’re on the same page.” With that, Pulitzer placed a small box in Davey’s hands, turned on his heel, and left the warehouse.

Davey’s heart dropped. He knew he’d been putting it off for a long time, but he thought he could buy another couple of years before this happened. Warily, he opened the box. 

Inside was the most ostentatious diamond ring he’d ever seen. Possibly a Pulitzer family heirloom, but more likely a personal reminder to Davey that he’d been dragging his heels about the betrothal for far too long.

A lighter set of footsteps approached. Davey hurriedly shoved the ring box into a pocket. “Hey, Bear,” he said, affecting his best nonchalance.

Sarah narrowed her eyes. “Good evening, palant,” she replied suspiciously.

Davey shook his head minutely.

Sarah sighed. “Let’s get moving.”

Davey gave her a weak smile in thanks, closed the hole in the false lumber pile in the back of the truck, and swung into the passenger seat.

Sarah silently hopped into the driver’s seat, flicked the engine switch on, and steered them out into the night.

Normally, Davey enjoyed the extra time he got with Kath and Sarah before their Sunday night parties. Today, though, the small black velvet box burned a hole through his pocket, into his stomach, and down through the floor. He was proud of himself for keeping any hint of composure at all, and especially for never running off to vomit from the stress.

Sitting on the bed in Kath and Sarah’s spare room, he pulled the box out and inspected it. The velvet felt new, and the ring inside shone like—Davey couldn’t afford to think of Jack and his beautiful eyes right now. Ensuring the ring was properly wedged into its cushion, he closed the box again and started tossing it from hand to hand. Maybe, if he wished hard enough, its contents would miraculously disappear.

Someone suddenly opened the door. Davey dove down onto the bed in an attempt to hide the box between his chest and the duvet, earning himself a slightly tweaked nose for his troubles.

“Hi,” Kath said, stepping in. “I knocked, but I guess you didn’t hear.”

Davey blushed uncharacteristically and refused to look up.

“Sarah said you’ve been off since last night, so I figured I’d drop by and check on you before your man gets here,” she added.

Davey peeked up slightly and maneuvered the ring box under his leg, then sat up. “Is that so?”

“David Jacobs,” Kath sighed. “You lost the ability to lie to me a long time ago.”

“I—look. I know we’ve been… anticipating this for a while. I just—I’m sorry this is the way it has to go,” Davey eked out.

“Spit it out,” Kath replied. “What’s really turned you into such a sap?”

Davey took a deep breath and set the ring box in front of him on the bed. “Your father visited me last night when I was packing up the truck. Gave me this. Also said you’d been seen with other men—what kind of trouble have you been looking for lately?”

Kath sighed and sat beside Davey. “I would say I’m sorry, but I don’t regret my independence. We’ve always said middle aisle-ing it won’t change anything. If anything, it gives us a little more security.”

Davey leaned his head on her shoulder. “I suppose you’re right. I’m just—I don’t know how I’m going to explain this to Jack.”

“Jack’s not stupid, David. This engagement may surprise him, but I know he’ll listen and understand when you get the chance to explain.” Kath took Davey’s hand and squeezed it. “Anyway, just for the hell of it—I wouldn’t mind if you got down on one knee.”

Davey rolled his eyes but dutifully slid off the bed and knelt in front of her. “Katherine Ethel Pulitzer, I’m sorry this is the worst proposal imaginable.” He opened the ring box. “Will you do your reputation, your father, and my father the honor of marrying me?”

Kath, unsmiling, plucked the ring from the box. “Wow, this must’ve been the most expensive thing in the Diamond District.” She slid it on her finger. “I guess it’ll do. Let’s share the happy news tonight.”

“Sorry again to start your night off like this.”

“David, we are victims of circumstance. Besides, we knew this had to happen eventually,” Kath soothed him. “Now I need to change into something that’ll match this, and you need to get off your knee and get ready to see your man.”

Kath saw herself out, and Davey beleagueredly dragged himself to the closet where his usual outfit for these parties had started gathering dust.

Putting on the suit felt like putting his armor back on—he’d forgotten how much he let his guard down with his sister and now-fiancée. Each piece he donned hid lanky schoolboy David Jakobwicz and brought back another fragment of mob-hardened David Jacobs, fiancé to one of the wealthiest heiresses in New York City. Of course, when he saw Jack tonight he knew he’d crack a little and become Davey Jacobs, pseudo-mob rube and outstanding torch bearer.

The simple black and white of his suit would both complement whatever Kath decided on wearing and allow him to disappear into what tended to be a more ostentatiously-dressed crowd, should he need (and, given the news he was about to have to announce tonight, he would).

Just as he finished securing his plain gold cufflinks, someone gently knocked on the door.

Davey grumbled under his breath. “I’m decent,” he announced to his visitor.

Sarah gently stepped inside the room and shut the door quietly behind her. Wordlessly, she sat on the bed and patted the space beside her. Davey, following her lead, sat next to her and leaned his head on her shoulder. Though he’d just finished putting on his armor, she’d stripped it away again in a matter of seconds.

“I’m sorry about your apartment. I know you liked it,” she said.

“I—what?” Davey’s mind had been so occupied by fear and panic that he lost the ability to read subtext.

“Your apartment, David. The one you’ll be moving out of after your wedding,” Sarah clarified.

Davey’s apartment was the least of his concerns at present. “I just—I thought we had more time. I need more time. I didn’t want it to happen like this.”

Sarah pulled him into a hug. “You’ll be okay, misiaczku. We know what’s real and that’s what matters. Besides, weddings can take a long time to plan. Things don’t have to change immediately. I’m always in your corner—don’t forget that. For now, though, we all have a bit of a show to put on.”

Davey nodded into her chest, feeling like he was six years old. He didn’t understand why he was moping this much either, but something about the way the ring had been put into his hands still didn’t sit right. He finally sat back up, wiping the tears that’d been forming out of his eyes.

“There we go,” Sarah encouraged. “I know this may sound a bit absurd, but, for tonight—pretend it’s Jack. Treat her the way you want to treat him. Pretend it’s what you always wanted. The more you sell it now, the safer we all are later.”

Davey nodded, building up the iron bars around his heart once more.

Sarah pulled him up to his feet and gently shepherded him into the living room, where she produced a deck of cigarettes. “For your nerves,” she explained.

Davey took two out of the box, handing one back over to her. Sarah nodded gratefully, put the box away, pulled out a lighter, and lit both of their cigarettes. Davey took a long drag. As with many of Sarah’s ideas, it did, in fact, help.

He let himself sink back into the loveseat he found behind him, his nerves melting away with each puff.

What felt like hours but couldn’t have been more than thirty minutes passed. Eventually, Kath joined, having really put on the Ritz with a glittering golden dress that nearly outshone the rock on her hand. Plain cigarettes were, of course, too plebeian for her, so she popped one in her cigarette holder, which Sarah lit for her.

Smoke curled up towards the ceiling and through the air, beginning the gentle haze that muted the sharper elements of Kath and Sarah’s parties. Time flowed like molasses as people started filtering in. Davey knew that Kath and Sarah had put on the record player and started greeting guests at some point, but he couldn’t tell when. Sarah had left the deck with him, so he lit the end of each new cigarette with the embers of the previous, tossing the stubs into an elegant ashtray on the table beside him. Someone handed him a drink. He sipped at it, letting the burning sensation of the alcohol wash away his anxiety swallow by swallow.

Just as he was about to light up another gasper, someone took him by the arm. Davey turned towards Kath, who had taken his left bicep at exactly the right angle to make the ring on her right hand glaringly obvious. She had a look of determination about her as she pulled him to his feet, and he let Sarah’s words from earlier wash back over himself. Pretend it’s Jack. Pretend it’s what you’ve always wanted.

Davey let a nervous but giddy smile slide onto his face, gently lifted Kath’s cigarette holder from her right hand, and tapped it against his glass a few times. The room fell silent.

“Welcome, everyone!” he shouted over the record player.

“It’s about time you showed back up!” Henry Gliksman called from the back of the room.

A laugh rolled through the crowd.

“It’s a shame—I was busy avoiding you, Hank!” Davey joked back. “But that’s not why I’m here. I’d like to give a toast”—he raised his mug—“to my fiancée tonight. Katherine, here’s to you!”

Davey knocked back the rest of his drink as the crowd cheered, then pulled her to his side and gave her a quick kiss on the head.

“Nice one,” she whispered into his chest before pulling away to look up at him.

“Go show off your rock,” he replied quietly. “Your father spent a lot on it.”

She laughed, then seemed to whirl away into the crowd. Henry had appeared at his side at some point and gave him a strong thump on the back, which almost made him choke—Davey must’ve had more to drink than he realized.

They exchanged pleasantries, skillfully avoiding the many elephants in the room. Davey’s brain felt fuzzy and warm. Pretend it’s Jack echoed over and over and over again. Bill and Darcy soon joined them, and Davey was grateful for the sort of guard they formed against other guests. His companions knew certain truths of the situation, particularly the game of respectability they all had to play so that their more brutal dealings would go unnoticed. Davey’s usual air of stoicism and stillness was serving him well on a night that had him feeling more jumbled than he ever had before.

A beam of light came in—the door must’ve opened. The record player stopped. Davey subtly turned slightly to watch. If Sarah could see him, she was going to rib him for this later, but he could live with that. There stood Jack, backlit by the stairwell lights, in a deep blue jacket that for some reason made Davey want to step out on a fire escape and drink in the midnight air. Kath quickly swept Jack away, and Davey, to keep up appearances, returned to his conversation.

The piano and Sarah’s voice began to soar over the crowd, Jack joining soon after. Davey couldn’t focus on anything, so he lit up another cigarette. The smoke softened the sharp edges of the background noise and chatter. He nodded along with Bill, Darcy, and Henry’s conversation, laughing where appropriate.

An arm slid into his—Kath returned to his side. 

Pretend it’s Jack, Sarah’s voice echoed in Davey’s mind.

“Sorry, fellas, but this gal’s feeling a bit lonely,” Kath said, tugging at Davey’s arm. “We’ll see you around.”

Davey could only mutely wave goodbye to his friends and stumble along behind her. She guided him to the loveseat nearest to the piano, which had been left miraculously vacant, and sat them down.

“Remember, we’re in love. This is the happiest moment of your life,” she hissed in his ear. He sensed her smile, usually reserved for Sarah, as she slung her arm around his shoulder.

Davey, thinking of Jack, leaned down and kissed her cheek.

“As long as we keep saying something to each other, you don’t have to kiss me,” she whispered.

Davey laughed quietly. “I suppose this works.”

He kept his eyes on her, trying to remember enough of the English language through his haze as she kept chatting with him. He dutifully laughed properly and eked out a few words every now and then, so the most he could pay attention to of Jack’s performance was the slowing tempo of each song and the melancholy that seeped into the music over the course of the set.

The music stopped, and Davey felt a gaping hole open in his chest.

“Thank you all for having me here, especially Kath and Sarah,” Jack shouted over the applause in the room. Davey turned away from Kath; he felt he’d canoodled with her enough for the night. Some people around him cheered. 

“ I, well. You all may know that this isn’t the only place I perform,” Jack continued. Another few people cheered—Jack must’ve become quite the celebrity. Davey wasn’t surprised, but the thought did make his hackles rise. 

“Yeah, yeah, I know,” Jack pressed on. “Sounds like the beginning of a great marketing pitch. However, I’ve just been the opener there for the lovely Miss Medda herself.”

The crowd somehow got louder, drowning out any of Davey’s worries.

Jack seemed to straighten up. “She’s been so good to me, but now she’s moving on. I don’t know if I’m allowed to let you in on all the details yet, but you all can keep a secret, right? Soon, you’ll be able to find her on none other than the Great White Way. Maybe it’s not as white anymore.” 

Davey allowed himself a quiet chuckle.

“Needless to say, she won’t be performing at her club, Miss Medda’s, anymore. But I’m not going anywhere—she’s left me with some big shoes to fill.”

Davey’s stomach dropped. Miss Medda may not have known how risky it was to put Jack into even more of the spotlight, but he did. He wished Jack—or someone—had told him earlier so Davey could’ve warned him about how monumentally stupid it was to become a well-known performer when all of New York City’s most dangerous bootleggers were in on your operation. 

Jack was looking directly at him. Davey couldn’t breathe.

Jack smiled bittersweetly. “That’s right, folks. Starting tomorrow, you can catch little old me as the headliner at Miss Medda’s all the way up in Harlem.”

“But—” Sarah interjected from beside Jack. 

Davey couldn’t bring himself to look away.

“Yes, this is unfortunately another case of good news and bad news. The bad news is that… well. You all have been witness to my final performance outside Miss Medda’s for the time being.” Someone started a quiet, good-hearted boo.

Jack’s gaze shifted to just beside Davey. “I couldn’t thank you enough for that,” he said, inclining his head to Kath. “I’ll miss being here and singing with this lovely songbird”—he gestured to Sarah—“but I’m fairly certain this is a see you later, not a goodbye.”

Davey stared, slack-jawed, as Jack pulled on his jacket and checked his pockets, suddenly hurried. Jack brusquely turned towards the door and saw himself out as Kath and Sarah called after him.

Kath elbowed Davey. “Go.”

He didn’t need to be told twice. Energized by the adrenaline of his pursuit, Davey lurched out of the loveseat and walked as quickly as decorum allowed towards the door.

Once he’d shut it behind him, he stumbled down the stairs, hearing what had to be Jack slamming the front door to the building below him. Mercifully, he didn’t trip on his way down all five flights. He shut the building door behind him, then looked both ways. Spotting a dark figure retreating to the north, he started an uncharacteristically inelegant sprint in that direction. Davey really needed to be more careful about his drinking at these parties.

“Jack!” Davey called once he was close enough to verify he was in fact following the right person.

Jack picked up his pace.

Davey grumbled but kept running. Finally, he got close enough to grab Jack’s elbow. “Jack. Please. We should talk.”

Davey could feel Jack pulling away and kept his grip firm.

“What is there to talk about?” Jack said, unaware of just how fruitless his struggle was. Davey was quite practiced in continuing tough conversations. “I have eyes.”

Oh. This was about the engagement. Davey let his affection for Jack rise to the surface. “Please, Jack,” he pleaded. “I swear it’s not what it looks like.”

“I don’t see how that’s possible,” Jack retorted, finally wrenching his arm away as Davey’s grip loosened. “Thanks for coming. Goodnight.”

Jack started running.

Davey, thunderstruck, watched him for a moment before remembering he needed to keep following. Unfortunately, the alcohol and nicotine flooding his system finally overtook him as he followed Jack’s disappearing figure into a subway station. Davey was just running down the stairs as he saw Jack, smiling, aboard the train pulling away from the station. He was too late.

Chapter Text

Davey wanted to collapse on the subway platform.

Just enough of his sense of self-preservation remained that he managed to drag himself back up the stairs, through the turnstiles, and to his apartment, which was slightly closer to the station than Kath and Sarah’s. He couldn’t bear to face another human being until he’d slept away the worst of his drunken misery.

Once he’d locked the door behind himself, Davey found that the cocktail of adrenaline and despair running through his veins wasn’t going to let him sleep anytime soon. Gracelessly draping himself across his beloved armchair, he gave heed to the thoughts racing through the sludge in his brain. Apparently, he and Kath had managed to sell their engagement well enough that Jack wouldn’t believe that it was a farce. Jack’s despondence throughout the night followed by the cruelty of his announcement ricocheted like a well-aimed bullet through Davey’s heart and mind. How had he not been informed of Jack’s promotion earlier? What good was his network of informants and criminals if something this important had bypassed his notice entirely? Had someone he knew been at Miss Medda’s at all the night this was announced?

He needed answers. Even though he couldn’t sleep, he knew he couldn’t trust himself enough in this state to actually kick off any plans. But—he could start plotting. 

Davey would likely be turned away at the door at Miss Medda’s, so a direct approach wouldn’t be possible. Kath was definitely not an option either, given her involvement in the engagement. Sarah might be able to get away with visiting, but not as regularly as surveillance would require. Henry, though…

Henry wasn’t known to Jack. He wasn’t too tall and didn’t have any particularly distinguishing features—making him nondescript enough that he tended to blend in with most crowds. Plus, Davey wouldn’t need to worry about his discretion. Henry was also sufficiently sociable to have a rotating group of people with him to hide his consistent attendance. Perfect. Davey planned to contact him the next day.

His mind wandered away from logistics and back towards Jack. He seemed inordinately upset about the engagement—were Davey’s feelings reciprocated? In some ways, that would make things easier, but others would become far more difficult. Davey wasn’t sure what to do about his world of secrets and lies, especially how to let an outsider in. His heart betrayed his mind in this case, and he was sure he could find a way to at least have some of Jack for himself.

He still did want to get in touch with Jack somehow. Attempting something face-to-face during his weekly deliveries wouldn’t amount to anything, and being too subtle risked Jack never cottoning on to his interest. There weren’t many ways to get in touch that wouldn’t risk the fragile security of the bootlegging operation, but maybe some sort of hint would work. Perhaps a note in the delivery could lead to, at least, a conversation.

Having exhausted his capacity for epiphanies for the night, Davey, now teary-eyed with delirium instead of outright devastation, dragged himself into bed. He didn’t bother undressing, though he knew he’d regret it in the morning. He’d more than earned that punishment.

Davey woke with a start. The room spun as he dragged himself out of bed to upchuck into his bathroom sink. Heaving, he groaned and wiped the back of his hand on his sweaty forehead. The sensation of his own fingers across his skin reminded him of the way he slid that ring onto Kath’s finger, and he hurled again.

Typically Davey could hold it together, but for some reason the engagement was still his weakest point. He groggily washed his mess down the drain and brushed his teeth, trying to recollect his scattered memories of his return home the night before.

Jack permeated his thoughts. That wasn’t entirely unusual for Davey these days, but he gripped the sink a little harder and worked his way further into his memory for something else.

Henry. Davey was going to seek him out once he didn’t need goggles for anything brighter than candlelight. Henry was smart and put-together in a way Davey couldn’t trust himself to be around Jack. He’d be a good source of information on Miss Medda’s while Davey was unwanted there.

Davey, meanwhile, thought back to the last of his plans. A note in the delivery wasn’t particularly secure, but hopefully he could be vague enough that whatever (or whoever) might greet him wouldn’t be beyond his capabilities of dispatching with. If luck was on his side, he’d get to see Jack. In a less lucky situation, he’d look like a fool loitering in the alley. Worst case—Davey didn’t want to think about those possibilities. Ideally, he’d walk out alive, and that was the most he could hope for.

Finally coaxing himself out of his bathroom, Davey dragged himself to his kitchen and made the largest cup of instant coffee he could tolerate. Hunched over his tiny table, he sipped at it and felt the fog slowly drip away. Even as coherent thought returned to him, Davey could not begin to compose his letter; instead, he filed a reminder to write it later somewhere in his mind.

Meanwhile, he considered how best to approach Henry. From the little Davey remembered beyond his despair, Henry had remained relatively clear-headed throughout the party, so he likely wouldn’t have been asleep for nearly as long as Davey had been. He’d heard about phone calls getting snitched on, so he likely needed to find Henry in person. The question now was just where he’d be—his apartment, with his family, or on a job.

Suddenly, Davey’s head started pounding again. In the background, he faintly noticed the sound of his phone ringing. Luckily, he could reach it without getting up.

“Hello?”

“Oh, good. You lived,” Sarah said, inducing a wince and a hopefully inaudible groan from Davey. “Ah. Barely.”

Davey grumbled. “I could hang up.”

“Oh, but torturing you through your hangovers is a particular pleasure of mine,” she replied.

Her small laugh intensified his already throbbing headache. “What’s so important?” Davey gritted out.

Sarah took a breath, and it seemed to Davey that she could possibly telepathically sense how his hangover was the smallest part of what was making this morning so miserable. “I—we—you should come over later when you get the chance.”

Sarah’s hesitant tone made Davey’s hackles rise. He rubbed his forehead, trying to will his headache to at least somewhat ease. Still, he couldn’t bring himself to speak.

“Alright, I get it. Just come over when you’re less heartbroken and more sober.” The harsh click of Sarah’s abrupt hang up had Davey automatically reaching to hang up his phone and collapsing back onto the table. No matter how much his world had been shattered over the past 24 hours, it seemed the Earth would keep on turning.

Laying face down on the table was becoming uncomfortable for Davey. He breathed in some cigarette ashes stuck to his shirt and broke out into a coughing fit, desperately trying to keep his sorely needed coffee in his body. Unsuccessful, he coughed up a bit of bile onto the sleeve of one of his few nicer shirts, sighed, and took himself to his bathroom to clean up.

Now as fresh-faced as a person could be after the worst night of their life, Davey contemplated how best to avoid Kath and Sarah without making the fact too obvious. He did need to catch Henry one way or another, and he could use the walk, so he started meandering over to Henry’s nearby apartment.

Davey mindlessly followed his usual path, looping around a few unnecessary buildings and making a few extra left turns to throw off anyone tailing him. Upon arriving at Henry’s building’s door, Davey pulled out his keys. Since his line of work was so unpredictable, it was easiest for him to have access to his men’s places, and Henry was his closest colleague besides Kath and Sarah. He let himself into the building, dragged himself up the stairs, and tapped out his usual knock on the door.

A groan came from the other side of the door. It took all of Davey’s composure to keep a wry grin off his face—at least his friends were somewhat suffering the way he was, too. He stood quietly, counting down the seconds until Henry reached the door in his usual quiet way. Even hungover, Henry kept his footing. Davey was a little jealous.

The door opened slightly. The room behind was pitch black, and Henry’s shadowed figure recoiled from the hall light.

“Come in,” he grumbled, urging Davey in. “You can’t hurt me worse than that light.”

Davey slid in the narrow gap, taking care to close the door quickly and quietly behind him.

Henry lit the half-melted candle on the single table in his tiny studio. “Electric lights are too bright right now,” he grunted.

Davey couldn’t begrudge him that, though he was curious how Henry had managed to get himself into such a similar state to him. Davey knew he’d been overdoing it, though after the day he’d had he felt it was justified. As far as he knew, Henry had not faced the same kinds of pressures that day and was far clearer-headed for all of the party that Davey had seen him at, having not succumbed to an old chain smoking habit immediately. Something must have happened after Davey’d run out to catch Jack, but now was not the time to pry—there were more urgent matters he needed to get to first. “Frankly, I’m not faring much better.”

“Cheers to that,” Henry replied flatly, taking one seat at the table and gesturing to the other. “Sit.” Davey obliged. “What brings you here, anyway? Normally you’d be at Kath and Sarah’s, not here. I mean, I’m honored, I guess, but something’s gotta be up.”

Henry sounded strangely edgy for someone as hungover as he was. Davey wanted to probe, but he didn’t have much time. “Yeah, uh. It is, unfortunately. Up. Something’s up.” Davey’s memories of Jack fleeing nearly had him tongue tied for a moment.

“Spit it out,” Henry sighed.

“Yes, sorry. I—well. You heard Jack’s announcement last night, right?”

Henry seemed to be making several mental calculations. Davey didn’t like how unreadable he was. “The singer, yes?”

“Yeah.” Davey finally felt some of his mob persona overcoming the pounding in his skull. “I need you to keep an eye on him. On Miss Medda’s. Every night. Don’t always gotta be you, but someone’s gotta be there.”

“Why can’t you? Not like too many people know you up there, and we already took care of your little problem.”

Henry was uncharacteristically defensive. Davey wasn’t sure why. “He knows me, but also I’m kinda persona non grata after last night. It’s best if it’s someone he doesn’t know. Makes you look like new audience members rather than surveillance. And even though we did somewhat take care of Spot, it’s best if he sees as little as possible of me in the near future. Don’t want him trying anything.” 

Henry softened. “Yeah, alright. You’re still their runner though, no?”

“It’s the only way I can keep an eye on their operation at present.” And perhaps also sneak a glimpse of Jack somehow, but Henry didn’t need to know that.

“Okay. Yeah.”

Davey started a bit. He hadn’t expected Henry to be so easy to convince.

“Don’t threaten me with a good time, Jacobs. You’re the one paying me to spend my evenings at a juice joint,” Henry grinned.

“Don’t go getting too zozzled, Mac,” Davey chided. “You’re still gonna be on the clock.”

“Of course, boss,” Henry replied with an oddly melancholic smile. “You don’t gotta worry about me.”

Davey tipped the hat he’d forgotten to remove in his still-addled state. “Thanks, pal. I’ll let you be. Hope tomorrow treats you better.”

Davey let himself out and nearly collapsed in relief before remembering his next stop. He didn’t have any more excuses to keep himself away from his sister and his fiancée, though he desperately wished he was in a state to invent a few more. Sighing, he trudged his way over to Kath and Sarah’s and cursed himself along the way for choosing to live so close to them.

By the time he was knocking on their apartment door, Davey hoped that whatever Kath and Sarah had for him didn’t require much effort on his part.

It seemed he was in luck. Sarah took one look at him after opening the door and swept him onto a chaise longue in the parlor, then added “You look like death warmed over.”

“Thanks, Bear,” Davey groaned.

Kath shut off as many lights as possible as she walked in. “We’ll make this quick,” she said, moving to sit on the edge of the chaise longue near Davey’s ankles. “My father pulled some strings and is now a producer on The Chocolate Dandies.”

Davey raised an eyebrow without getting up.

“Miss Medda’s show.”

Davey sat up too quickly, immediately regretted it, and collapsed back into the chaise.

“He’s working on finding us tickets to opening night—keep your calendar open for three Fridays from now.”

Davey halfheartedly saluted, and the women let him be.

The week crept by. Davey’s general sense of malaise overshadowed his work, but he hoped it wasn’t too obvious to anyone besides Kath and Sarah. As Saturday night approached, he started drafting his note to Jack in his head. It couldn’t be too specific, but there needed to be enough there that his point got across somehow.

Minutes before he needed to leave for the delivery late Saturday night, he finally scrawled out the letter.

Dear Jack,

I’m afraid I wasn’t able to fully explain myself last weekend. I can’t say much more, but please meet me at next week’s delivery.

Mouth

Davey pulled an envelope from his desk, quickly adding To Jack on it, then stuffed the letter inside. He tucked the envelope into an inner pocket in his coat, then set out for the warehouse.

Loading the truck took longer than usual. Davey needed to make sure he had a secure spot for his letter, and nowhere seemed good enough. He could hear Sarah getting antsy in the driver’s seat, so he gave up and tucked it in the middle of a case of whiskey.

As he slid into the passenger seat and closed the door, Sarah revved the engine and pulled out of the warehouse. 

Davey sat quietly, though he could feel Sarah’s frustration building.

After a few minutes, she gave up waiting for him to speak. “Got a good reason why we’re running late after weeks of efficient deliveries?”

Davey took a deep breath.

“David.”

He couldn’t breathe a word of his harebrained, half-hungover scheme to her. Not yet. It was too dangerous to let Sarah in even though Davey knew he could trust her.

Sarah grumbled under her breath at his refusal to speak, but she, too, was well-trained enough to know not to question him, as much as she wanted to.

The rest of the drive was tense but silent. Davey insisted on loitering in the shadows until the case with the letter was taken inside as Sarah drove a quick lap around the neighborhood, and he breathed a sigh of relief when he saw one of the other bartenders he vaguely recognized pick up the box.

“Oh, misiaczku,” Sarah said after she’d picked him back up. “You’re really gone for him, aren’t you?”

Davey’s eyes widened fractionally. Sarah was, perhaps unknowingly, giving him a bit of cover. He scratched at the back of his neck. “Just figured I’d see if I could catch him picking up the delivery. Guess since he hit it big he’s got other people to do it for him now.”

Sarah hummed, seemingly placated with his pathetic excuse, and they drove back to the Lower East Side in a more comfortable silence.

“...And then she kept pulling coins outta the piano!” Henry crowed.

Davey gave a quick, half-hearted grin. “Sounds fun. Also sounds like you got something to tell me that ain’t so fun. Spit it out.”

Henry sighed. “I don’t think the Irish and Italians are liking me being around,” he said, sipping his teacup of the most expensive moonshine blood and money could buy at Davey’s kitchen table. “Spot’s been a bit twitchier than usual the last couple of nights. Don’t think we scared him so good.”

Davey grimaced into his water glass. He needed to stay sober for tonight’s delivery, especially if Jack had read his letter. “Thought he didn’t know you? Bill and Darcy did the convincing, if I recall.”

Henry coughed and mumbled something indistinct.

“What was that?” Davey asked, raising an eyebrow.

“I… know his companion,” Henry gritted out.

Davey narrowed his eyes. Logically, he knew the odds were low he was the only guy who’d gotten involved with a member of another mob, but he hadn’t realized Henry could possibly have similar proclivities to him. Maybe he hadn’t been paying attention. He mentally kicked himself back into some semblance of composure. “Oh? How so?”

“Since, uh. Since around when you got to know Spot.” Henry’s cheeks were flaming.

Davey wanted to take Henry by the collar and shake him but managed to restrain himself. “He Italian too?”

Henry took a deep breath. “No. Irish.”

Davey set down his water glass with a shaking hand, then closed his eyes and took a deep breath. Opening his eyes, he leveled what he knew to be an intense stare across the table. “Why didn’t you tell me on Monday? Fuck, why didn’t you get literally anyone else to cover you? You know Medda’s is our riskiest buyer. What the fuck are you doing?”

“I didn’t see him til Wednesday, and by then if I stopped showing it’d seem stranger. Didn’t think he’d recognize me since it’s been so long. Thought Spot’d had a strong enough impression of us that we didn’t need to worry too much. Might be wrong about that one, though.”

Davey had to concede that, in any other situation, he would see Henry’s point. It was a reasonable enough conclusion to reach. But this was Jack. Jack’s life was on the line. Davey knocked his glass off the table. It shattered on the floor. He didn’t care. “That’s enough. I’ll clean up your mess tonight, and you’re going to send Finch and Jojo to replace you starting now,” he threatened. “Don’t go back. Don’t come back here, either. You’re lucky I don’t fill you fulla lead right now. Get the fuck out.”

Henry set his teacup down gently, pulled his coat and hat on, and slipped out of Davey’s apartment.

Davey locked the deadbolt behind him, then slumped against the door and slid down until he was sitting on the ground. In all likelihood, someone would be watching the delivery tonight, and it wouldn’t be Jack. The odds were high that he’d have to handle some sort of suspicion. He resolved to keep his pistol a little readier than usual that night.

“Please tell me you’ve got your gun tonight,” Davey nearly begged as Sarah steered them into the Manhattan night.

“Why wouldn’t I?” she replied, a bit confused. “What’s going on?”

“Think we might run into trouble tonight,” Davey said, keeping his eyes on the road. “Turns out Hank knows Spot’s Irish pal.”

“And?” Sarah prompted.

“And Hank’s been watching Miss Medda’s while Spot and co. do the same! Fucking hell, Bear! He’s gonna get Jack killed if he keeps this shit up!”

“Jack ain’t stupid, palooka! He wears iron just like you.” Sarah rarely dropped her proper affectation for the grittier argot of the mob, and, as much as he knew that it meant she was incandescently angry, Davey was comforted to hear it when she did. “Farthest he goes these days is maybe Midtown. You oughta worry more about yourself—I know you’re a good shot, but one gun don’t make up for six on the other side.”

“I got you, and you’re worth three of me at least,” he replied. “And Spot don’t know everything, but he does know cutting me down creates more problems than it solves.”

Sarah hummed. 

“Bear, we—well. You know we metaphorically kicked the shit outta him a few weeks ago,” Davey pleaded.

“That Irish buddy of his is a wild card, David. Could give old Spot some confidence,” she reasoned.

“Then it’s good you’re packing heat, too,” Davey said.

Sarah hummed in what sounded like agreement to Davey, so he left the conversation at that. They were nearing Harlem anyway.

In the quiet, Davey triple checked that his pistol was loaded, then cocked it and carefully slid it back into the holster under his left armpit, hoping he wouldn’t accidentally shoot his leg off during the drive.

As they trundled into the alley behind Miss Medda’s, Davey had a vague sense that someone was watching. Sarah braked uncomfortably loudly, and the truck came to a stop.

Davey took a deep breath, reminding himself that he was supposed to be a novice and not know that there was any possibility anyone else could interrupt his delivery, then cavalierly swung his door open, hopped out of the truck, and slammed it shut. 

He peeked up from under the brim of his fedora and registered some sort of human movement coming from one corner. Without thinking, he drew his pistol and fired just to the side of the person’s head, aiming to scare, not to kill. 

Spot Conlon shouted in surprise, and Davey briefly smirked, keeping his posture relaxed as he cocked his pistol and aimed it at Spot’s familiar tall, redheaded companion, who had just emerged from the opposite corner.

“Hands up,” Davey said, keeping his aim steady.

Wordlessly, Spot and his pal raised their hands. Each of them wore a ring on their right ring finger that caught what little light spilled into the alley. Interesting. Davey didn’t have time to think more about the rings at the moment, and he wished desperately that Henry hadn’t screwed up so badly so that they could discuss what was going on when he got back from the delivery. Kath and Sarah would have to do.

“Listen here, punks. You’re gonna leave this place the fuck alone if you value your lives at all,” Davey growled. “I better not see hide nor hair of you around here again. Next time I won’t miss. Are we clear?”

Spot stayed silent, but the tall man started stumbling over his words.

Sarah quietly stepped beside Davey, and he gave no indication of his surprise at her sudden appearance or the fact that she’d had her pistol trained on Spot since she got out of the truck.

“Capisce?” she added threateningly.

The two men nodded silently. Spot glared a bit at Davey. Selfishly, Davey was enjoying completely having the upper hand on Spot without having to pretend to be someone he wasn’t, though he didn’t show it.

Sarah shifted subtly, and Davey caught on to her plan. “Now scram. Separately. Follow us,” she said with none of her characteristic kindness. “And my aim’s better than his, so don’t try any funny business.”

Spot looked like he wanted to smile but knew he shouldn’t.

Davey and Sarah, true to her word, kept their steady aim and directed Spot and his companion down and out the alley with only their guns. Shortly after the pair left the alley, Sarah hopped back in the driver’s seat of the truck, and Davey continued the delivery as usual, doing his best to hide his shaking hands.

This wasn’t how the night was supposed to go—Jack was supposed to be at the back door and Davey was going to explain everything. Jack would understand and perhaps invite Davey in for a drink or potentially up to his apartment for something more. Davey hadn’t wanted to maim his teenage paramour, but Spot had left him no other option. Jack wouldn’t have been so stupid after receiving as many warnings as Spot had, though Jack also knew when things were his business and when to let things be.

After he shut and locked the back door to Miss Medda’s, Davey glanced up at the windows of the building. Most were dark with curtains drawn shut for the night, but one curtain in a fourth floor window was just barely pulled aside, revealing a familiar dark face. Jack. Davey felt all of the air leave his body. Jack had read Davey’s letter. He just didn’t trust him enough, which Davey figured he’d somewhat earned at this point.

Davey couldn’t afford to linger, so he got back into the truck, and Sarah steered them out into the night.

“David—” Sarah started.

“I’m tired,” Davey interrupted, then lowered his hat over his eyes. What more could he say?

The next Friday, Davey thumbed through the suits in his wardrobe. He’d never been to a theatrical premiere before, though he had accompanied Kath to his fair share of galas and parties and other hobnobbery, and he wasn’t quite sure what was appropriate to wear. Since he was Kath’s guest, he figured he needed to err towards wealthy Manhattan socialite rather than sharp and uncannily clean mob man.

That still left a solid third of his closet to pick through, and the knowledge that Jack would almost certainly also be at the premiere was not helping. He couldn’t go too flashy, but he needed to fit in with an artier crowd than usual.

Davey thought back to Jack’s spiffy blue jacket and the way it made him look like the most beautiful hours of the nighttime sky. The silver suit in his closet came to mind: moonlight to match Jack’s midnight. He had no idea if Jack would be wearing his blue jacket again, but, even if he wasn’t, Davey could cling to his memory of it and the possibly misplaced hope that Jack would be able to see the connection between their outfits.

Davey dressed quickly, then checked his pocket watch. He was right on schedule. Grabbing a matching gray hat off his coat rack, he slipped out of his apartment, locked the door, and headed to Kath and Sarah’s to catch a swanky chauffeured ride.

The car was idling outside Kath and Sarah’s building when he arrived. Davey breathed a sigh of relief when he noticed that the backseat was empty and slid in.

Moments later, the building door opened, and Kath and Sarah tumbled out, racing towards the car. They wore coordinating drop waist dresses—Kath in navy blue and Sarah in a yellowy gold, unintentionally echoing Davey’s mental image of the night sky. Piling in, they apologized profusely to the relatively stoic driver, who’d almost certainly seen worse. 

Kath and Sarah chatted lightly throughout the drive, somehow managing to befriend the driver in a matter of minutes. Davey mostly stared out the window as they passed buildings that got progressively more ornate as they continued north. He couldn’t tell if the vaguely nauseous feeling in his stomach was anxiety or dread, and he didn’t have time for the kind of self examination it’d take to figure that out.

Finally, they pulled up in front of a brightly lit marquee under which a thick crowd of people glittered and sparkled. The driver opened the door, and Sarah, Kath, and Davey stepped out of the car.

“Thanks, Romeo! You really are the leopard’s stripes!” Sarah gushed, waving the driver off. She beamed, then took Kath’s arm with one hand and Davey’s with the other.

Davey managed a small smile before putting his metaphorical armor back on.

Kath similarly let an emotionless mask slide over her face, perfunctorily passing out tickets and guiding them through the crowd to the entrance.

Davey tried to subtly scan for Jack, but quickly found that he couldn’t withstand the throng and keep Sarah’s arm in his  if he looked anywhere but directly in front of him. Instead, he opted to slide his hat down a bit to hide his eyes and kept it on even as they entered the lobby and headed towards an aisle. He knew it was rude to leave his hat on indoors, but he couldn’t bring himself to care.

Kath, Sarah, and Davey handed their tickets to an usher, received their playbills, and headed to their seats towards the back of the orchestra. This was a prime people-watching spot, and Davey would be damned if he didn’t make the most of it. He may be damned regardless, but that was beside the point.

It was difficult to identify anyone based on the back of their head, but Davey trusted that he’d know Jack when he saw him. Kath and Sarah chatted beside him about the show and some note that was in the playbill, and he earned the occasional elbow from Sarah for not paying attention to their conversation.

His efforts and minor rib ache were worth it when he spotted a familiar profile bent over a playbill in the third row. Jack was wearing a deep green velvet jacket that didn’t quite pair with Davey’s imagined night sky but was handsome regardless. Davey watched him take a deep breath, then cast his gaze around the gilded theater as if he’d never seen anything so wonderful before. Unshed tears gleamed in Jack’s eyes.

The orchestra began playing the overture, and Davey watched Jack jump in his seat. It probably wasn’t a good move to watch Jack through the entire first act, so Davey on occasion cast a glance towards the stage. The live horses were an entertaining if intriguing addition—he briefly wondered how well the backstage area was maintained to prevent performers from stepping in anything, but even that was not a compelling enough thought to pull him away from Jack for too long. To keep his cover, Davey tried to react consistently with the rest of the audience and was mostly successful barring the occasional unsubtle elbow from Sarah.

The lights came up as the audience applauded the end of the first act. Davey turned towards Sarah in a weak attempt to avoid Jack catching him staring.

“Look, misiaczku—Medda’s bio,” Sarah said, shoving her open playbill at his face.

Davey scanned the page. “ To Jack: all the world’s a stage. Find yours,” he murmured, reading the end of her biography aloud. “I’m glad he has her.”

“Me, too.” Sarah smiled, gently taking her playbill back.

Kath stood and stretched out her arms. “Can we stretch our legs? The show’s swell, but I need to move a bit.”

“Come on, lover boy,” Sarah taunted, pulling Davey with her as she got up. “Don’t get too dizzy now.”

Davey used his mob training to subtly shove Sarah into the aisle after Kath, then followed. “Ain’t got a dame to be dizzy over, Bear. That’s all you.”

Sarah threw back her head in laughter, then took Kath’s arm.

“That your man down there?” Kath asked, tilting her head slightly in Jack’s direction.

All Davey could do was nod. 

Kath grinned wickedly and started maneuvering Sarah and Davey down the aisle like salmon swimming upstream against the other theatergoers that were heading to the lobby. It took ages to make any progress despite the relatively short length of aisle between them and Jack, and Davey wasn’t particularly willing to throw any elbows to help.

“Ugh, we wasted too much time!” Sarah exclaimed as the house lights blinked to signal that intermission was nearly over.

Kath sighed and turned around, pulling Sarah back with her, which left Davey to stumble up behind them. He really needed to brush up on his theater etiquette.

The lights dimmed for the second act shortly after they had found their way back to their seats, and Davey used the excuse of the darkness to drop all pretense that he was watching the show at all. Jack captivated him—how freely he could express himself and his genuine excitement for this woman who was clearly so important to him made Davey a little jealous.

All too soon, the cast took their final bow, and Davey felt as wobbly as a baby deer as he stood to match everyone else giving the show a standing ovation. The house lights came up, and soon all he knew was that Sarah was taking him somewhere.

A few minutes later, Kath and Sarah were shoving him into a cab in front of the theater and giving the driver a fake address a few blocks away from his building with well wishes that had the firm subtextual warning to not concern himself with whatever scheme they had concocted this time. 

Davey paid the cabbie handsomely upon his return to the Lower East Side, then automatically took a winding set of turns back to his building. He was glad that Kath and Sarah had picked one of his more frequently used fake addresses, as his still-bewildered state didn’t give him the capacity to work out a new route while processing everything else that had happened that evening.

He’d only seen Jack from a distance tonight—how was he so far gone over this man that just being in his presence made him forget everything he knew?