More Team Sky/Nightsky Headcanons! Warning for Nikey being a little bit of an ass for the stuff under the cut.

Nikey had to end the life of a close friend he held dear to his heart as they started to make plans to overthrow Nikey and take over Nightsky. Nikey found out right before the planned day of being overthrown, and had no choice but to take their life in order to save his own.

Winona and Nikey both have Pokémon that they rescued personally due to Nikeys actions. Winona rescued a sillicobra she found dying in the cold dessert sands, she took it in, nurtured it, and ended up adopting it. It ended up evolving into a Sandaconda which she always keeps with her, along with her Umbreon and Espeon. All three make a great pairing in case of sudden emergency rescues while Winona is out and about.

Nikey had rescued a Purrloin from certain death of falling off one of the sky islands after getting into a tussle with other wild Pokémon. After Nikey had dropped nearly everything to go rescue this Pokémon, on the flight back up to the sky island it’d fallen off of, Nikey noticed the poor kittens left eye had been scratched out and was causing it great pain. Nikey took the Pokémon to one of his personal Pokemon doctors out of sympathy, and ended up checking on it every day as it recovered. He ended up adopting the kitten and using it as his own pokemon. Anyone who questions him having a land Pokémon on his team gets docked pay.

The purrloin would often also have nightmares due to its traumatic experiences in its life, so this only boosted Nikey’s sympathy for it even more. This purrloin ended up becoming a representation of recovery for him, but he didn’t really take it to heart as much as he could have.

Winona and Mikey’s wedding ring both had a heart with wings engraved on the inner parts of them.

Winona and her colleague’s ship name is Teatimeshipping (I PROMISE the colleague will get a name soon.)

Winona had to hold a pretty much worldwide funeral for Nikey after everyone realized he was never coming back, and everyone accepted he probably had died. During this funeral, it is told the world was united once again under Winona. There wasn’t any bickering amongst the hundreds of thousands of people attending, everyone sat there and listened to Winona’s speech. All her woes and sorrows. Her regrets and mistakes. And everything she went through during the course of Nightsky. Half of the speech was almost entirely about her husband and how much she missed him, and now she’d never get the chance to fix things with him again, which she blamed herself for. The attendees sat in silence and listened until she got everything off of her chest, in which then, the world had begun to see a new light.

After Nightsky was disbanded and the smog was starting to be cleared, there were still some stragglers who didn’t want Nightsky to be disbanded. These stragglers started Neo Nightsky, who’s goals are pretty much more of the same as regular Nightsky’s, but they’re having more difficulties now that the world is finally mostly at peace.

World restoration efforts begin, but they would not be done for atleast an entire century, long after Winona is gone. She has to pass on her legacy to somebody, but I’m not quite sure who yet. Could she have adopted children? It’s very likely.

Winona got the opportunity to see Nikey’s office after he dissapeared and she just ended up sitting in there for hours silently crying, just looking at all that was left of him. Nikey ended up leaving his Purrloin behind, which had been roaming around the abandoned HQ. Winona ends up coming across the kitten and learns about its past with Nikey through a journal of sorts Nikey kept in his office. It wasn’t a diary, however he did have one back at his home. Which Winona couldn’t stand to go to, as she wouldn’t think she’d be able to pry herself away and leave.

Nikey’s purrloin ended up hanging around Winona for her entire visit. Her colleague ended up having to bring her out of the office after a few hours, Winona didn’t protest, but she did take awhile to actually leave, which she did in silence. As she was preparing to leave the island Nightsky’s HQ was on, she noticed the purrloin lurking about near her. She crouched down to its level and held out a hand to it, which it responded by skittering up to her and pressing its head into her palm, purring. Winona was overwhelmed by emotions, and ended up taking it home, along with the rest of Nikey’s Pokémon he had left behind. (Which does not include Rayquaza.)

Winona is the embodiment of the song When You’re Gone by The Cranberries, also Once More to See You by Mitski. Also I Bet on Losing Dogs by Mitski.

a little bit of a massive mood change under the cut

Also fun fact Nikey had a certain someone he was close with, and was one of the only people he trusted. Her name? Maddie. Maddie is the owner of an actually magic magic hat that she found when she was a child. Unbeknownst to her at the time, this hat would be the cause of her losing her friends, everyone she loved, and being taken in by her aunt, Why? Well, you see, this hat has the ability to summon any legendary Pokémon the wearer desires, except, the only person allowed to wear this hat is Maddie. As if anyone else touched the hat or steals it, they end up in a catatonic state.

Maddie cannot leave the hat behind anywhere, as it will always find her one way or another. As you can imagine this took a large toll on her as a person. One day, she heard about Nightsky, and about Nikey as well. She thought, “HMMMMMMM. Yeah I’ll try my luck with it, sounds like a fun time.” She ended up becoming the teams “magician” (though that’s only a cover for why she’s actually there.) and would often put on performances to boost the moods of Nightsky’s members, beloved by all. Nikey, knowing the magic hats true capabilities, ordered some of his own bodyguards to guard Maddie herself as well.

This ended up with them often spending time together when neither of them had to do anything else. And unfortunately for Maddie, she started to catch a little bit of a crush (a fucking massive one.). This ended up becoming a very unhealthy thing for her as she would do almost anything for him. (Which is what made her so trustworthy to him.). Nikey knew about the crush, it was pretty obvious to him, but he didn’t do anything to try and stop the crush. It was out of his hands either way, and he didn’t want to make Maddie feel bad for something she couldn’t control. What’s this? Is he developing a soft spot for her? Uh oh. Nikey didn’t end up developing any feelings for her back, but would often find himself playing with her own feelings for him. He hated himself for it, but it just became an unhealthy habit, unhealthy for both of them. Nikey ended up leaving before anything could escalate too much, but Maddie still has very complicated and unresolved feelings for him. (DISCLAIMER. They did not end up every doing anything sexual with eachother because NO. BAD.)

IT ENDS UP BEING A WHOLE THING AND GIANT MESS AFTER WINONA FINDS OUT ABOUT IT FROM MADDIE AND SHES LIKE “…??.??.?.?. Huh???” And it’s like she’s upset at first but then she remembers she sort of did the same thing with her colleague except it wasn’t the same thing at all, because they had genuinely fallen for eachother while Nikey was making questionable decisions and it’s just a whole thing.

Maybe Maddie, Winona, and her colleague get together in a polycule after a while. :) I love Maddie she is the woman ever

I’ll post an image of her some time in the future

For now, just know that she is the embodiment of the song Magic Hat by The Scary Jokes

Post End.