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English
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Published:
2025-08-15
Completed:
2025-11-26
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3/3
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A Brief History of Oscar Diggs, the Wizard of Oz

Summary:

"Oscar Diggs, the self-styled Wizard of Oz, was born in New York City in 1850."

Chapter 1: Oscar Diggs
Chapter 2: Jellia Jamb
Chapter 3: Canon Difficulties

I decided not to continue past Chapter 2, as this diverges so much from Canon. I'm leaving it up in case anyone liked Chapters 1 and 2. I am keeping Jellia's family for future alternative Oz stories.

Chapter 3 quotes what I consider one of the more difficult passages to reconcile in the original books. I had meant to go with Oscar Diggs being an unreliable narrator, i.e. a liar.

Chapter 1: Oscar Diggs

Chapter Text

Oscar Diggs, the self-styled Wizard of Oz, was born in New York City in 1850. His father was a two-bit politician who had relocated from Philadelphia following certain inquiries into the movements of city funds. Oscar's father had settled in New York and ingratiated himself with the local political machine. His plan was to hide out a bit before seeking higher office.

The disgraced politician married and produced a son. The parents had named him Oscar Zoroaster Phadrig Isaac Norman Henkle Emmannuel Ambroise Diggs, for as his father said, he might need aliases some day, and it's best to have some of them be legal. His mother's input had added 'Oscar Zoroaster', for reasons known only to herself. But she was a minor witch, and so the father shrugged at this addition.

The son was precocious from a young age, and Oscar's father determined that he would get the best education he could find. The father began a laborious five minute inquiry among his peers, and it was determined: the young Oscar would attend the closest Catholic school to home. Of course, there were concerns. Oscar's father felt vague fears that the boy might accumulate some sort of moral code. That could curtail his chances of rising in society. Rising to political office might prove impossible. Oscar's mother did not want her child to worship what she called "the unproven newish gods", but to commune with the ancient Fairies, which she knew to be real. Her family was from the Old World and still held to the Old Ways. But in the end, it was cheap, so it seemed an acceptable risk.

Even before entering school Oscar was speaking English and his mother's native tongues. Soon after entering school, he was reading voraciously in several languages. He had learned Greek before New Testament studies had begun, and was moving onto the old Greek poets. He devoured all kinds of books: rhetoric, mechanics, mathematics, history. And he had developed systems to aid retention of what he read. Oscar's mother wondered if her son had been marked by the Fairies as thanks for her continued reverence of them, though she had never seen a Fairy Mark. But she was worried, for the nuns had told Oscar that the witches were all dead now.

Oscar's father became almost afraid: surely there was such a thing as too much book learning! It was the sort of ill-defined menace which politicians sense when something surpasses their understanding, which is often. But in this case, Oscar's father did not mount a campaign against it.

By age ten, Oscar had outstripped the teachers at school. He tutored wealthier classmates for money, doling out rhymes and other memory aids; it kept them coming back. His father liked this; it soon opened up doors for him, and he rose to a higher position, both in politics and crime, for the two spheres overlap to a great extent.

Now, some people worried that Oscar's father might be smart like his son; but an old mafioso (who remembered a bit of logic from school) won the argument by reciting dozens of situations which clearly demonstrated that Oscar's father was as dumb as his son was smart. The old mafioso had the others around his table almost rolling in the floor with tales of Oscar's father's stupidity.

By the time Oscar was thirteen, he would quickly finish his lessons during class so he would have time after school to hustle games. He found he could make quite a good income beating adults at poker, chess, and all kinds of other games. This made his father proud: all that education was paying in cash!

One day, Oscar's father was arrested. He had been too cheap to keep the bribes paid up. Young Oscar became the man of the house. Tutoring began to dry up, for rich people cut ties to Oscar's father. This was not out of any sense of morality, but due to fear of legal penalties. No longer having to go to school, he devoted himself completely to hustling. His mother went to work in an import office. Yet even the hustling began to become harder. Without support from his father and his friends, Oscar was getting shaken down for a sizeable cut.

Oscar was being pressured to work for the old mafioso. One day, he had been roughed up, and he decided that he could no longer stay in New York. "Watch the head; that's what he's good with," is what the guy in charge of the beating had said of Oscar.

Oscar helped support his mother until he was sixteen; he disappeared one day, but he left her half of his savings and a brief note. Oscar had always kept back a portion of his winnings, for he had not wanted his father to know how much he had. His mother married a successful stage actor and lived comfortably into old age.

He had read about the bustling West, and came to believe it held more opportunities than New York, where his father would be on the outs with the political machine. Young Oscar worked his way from town to town, hustling in dive bars to get by. He learned how to avoid organized crime by not making his talent obvious. He arrived in Chicago, but found little use for his talents. No one wanted to play games or get tutored in this place. He held a number of clerical and editorial jobs over the years. He wrote quite a bit of advertising copy. Oscar was valued. He could quickly diagnose, and in many cases fix, the printing machines and typing machines himself.

He had tried to get a job using his aptitude for mechanical devices. He went to a mechanic shop. The boss took a look at his scrawny frame and said to lift a weighty machine overhead. Oscar had asked what purpose that would serve when he could employ simple tools to move it. The workers in the shop laughed and laughed. Oscar said he would never try that again.

As Oscar entered his early twenties, he developed a taste for gin and a disinclination to stress his mind. His wit was blunted. At twenty-five, Oscar went to a traveling circus and saw a way out of his ennui. Oscar pushed himself in and so impressed the owner that he was hired on the spot. Oscar enjoyed spinning stories and blustering before the crowds. It restored his confidence. He had always loved to hear himself speak, and speak he could! Crowds enjoyed his playful, encouraging speeches; he drew crowds. They willingly parted with their money and didn't feel bad afterwards. They wanted to come back for more.

But a year into his new career, Oscar fell out of favor with his first employer. Thereafter, he worked in various smaller shows, traveling the West. Oscar was demoted to flying balloons and doing parlor tricks for the crowds. As always, he was good at it. He didn't care much for the balloon rides, for he wasn't allowed to learn much; he was just expected to ascend and descend, the balloon tethered to the ground. But Oscar tore into learning magic tricks and invented his own. But what he really yearned to do was bark to the crowds.

One night in Omaha, Oscar had a terrible argument with the manager of the show after that night's magic show. Oscar downed a great deal of gin, well past midnight. When he opened his eyes a couple of hours later, he had the worst hangover he had ever experienced. He would do no magic tricks that morning; the manager could fire him if he wanted. Without thought, Oscar dragged himself out of bed to prepare the balloon for the midday show. Maybe he could get in a nap before then. If Oscar had had his wits about him, he might have noticed that the knot securing the balloon was not tight.

Oscar dragged himself back to his cot to try to rest a bit. He nibbled a few crackers and lay in the awful, cramped cot. He couldn't get to sleep, but he kept lying there, trying to at least rest his eyes.