Hi, My Name Is Allan, and I’m a Compulsive Gambler

By The Free Press | Created at 2025-03-09 15:41:42 | Updated at 2025-03-09 22:15:47 7 hours ago

I started gambling in the hallways of my middle school in Chicago when I was 9 or 10. My friends and I would play some corrupted version of poker; we’d give each other no interest loans, and be late for class.

I didn’t know it then, but this was the beginning of my years as a compulsive gambler. I was on my way to rock bottom—a place I’d go on to visit three times before I finally cleaned up my act.

Around 11, I learned how to read the betting lines—those are the point spreads used to determine the odds for a given bet—in the Chicago Sun-Times. Soon I was making up different characters, giving them bankrolls, and tracking their bets using the newspaper. I named them—they were always men—and kept track of all their information (who was up, who was down) in a series of notebooks. I’d make all their bets. I did not get good grades.

By the time I was 13, all I wanted for my birthday was my own bookmaker. My friend Randi’s father was a bookie, and I would incessantly ask him to be mine. “When you’re 18, kid,” he would bark back at me, cigarette falling out of his mouth.

While the rest of my friends were getting interested in girls, I retreated into the world of the gamblers that lived in my notebooks. Each of their net worths was very important to me. I used the financial section of the Tribune to give them stock portfolios. The local real estate listings determined the value of their homes. I kept brochures of the newest Porsches and Mercedes to fill their garages.

My guys let it ride on football games every weekend. Bears at Vikings, Cowboys at Giants, Sunday mornings through Monday nights, these gamblers didn’t miss a game. Very few made money. Most went broke, and when they did, I was forced to create new gamblers to play with. They were my degenerate Barbie dolls.

I was fortunate enough to eventually leverage this odd hobby into a career as a screenwriter, and yet too stupid not to heed the cautionary tale I was writing for myself.

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