This article was published in collaboration with Vice.
Sports gambling is a serious form of entertainment in prison. I’d guess maybe 30 percent of inmates bet on sports, at least where I was in the late 1990s, at Wyoming State Penitentiary. That’s where I learned the hustle, working as a ‘writer’ who collects betting slips and delivers them back to a bookie. I’d make 20 or 25 percent off the top, or $1.25 cents off a $5 bet, no matter whether the better or the bookie won.
It’s a great job because there’s no exposure. It was the actual bookie who had to sneak into the education wing of the place, where the copy machines were located, and find a way to distract the staff and make copies of the cards listing the odds for all the day’s games. Then he’d have to count and store all the winnings.
Perspectives from those who work and live in the criminal justice system.
In 2001, I was transferred to a federal prison. In addition to my five years for burglary, the feds had indicted me on conspiracy to distribute methamphetamine, and gave me just under 17 years. When I got to the federal facility in Yazoo City, Miss., I saw the action was ten times what it had been at the state level. So I became a bookie myself. Basketball was the most profitable because it happened every day, but individual football games could bring in a lot of money. I took in $7,000 worth of bets on one NFL Sunday. Generally, my goal was to make a profit of 25 percent.
I’d call family members or friends to get the lines — lists from Las Vegas of who is favored to win and by how much — that bookies use to set the odds. After a few years, the federal prisons brought in CorrLinks, a basic emailing system, and I could have people send me the lines that way.
In the Mississippi prison, nobody used actual cash; it was all stamps and mackerel. Fish was good because you could buy hundreds of dollars worth at a time from the commissary, whereas you were only allowed to buy one $10 book of stamps. At the end of the day, a bookie would have tons of little pouches of mackerel worth between $1.15 and $1.35. He could use them as currency on its own, or sell them for a buck each to weight-lifters who wanted to bulk up on protein.
I had up to 14 writers working under me. White guys and black guys who could go get bets from their racial groups. I also had a few writers who dealt with everybody — race never goes away in prison, but sports betting was often an exception.
Eventually, I was transferred to a prison in Coleman, Florida. A partner and I went into business together, and I made even more money down there. Some of the bookies didn’t know what they were doing: they wouldn’t know how to do the calculations and would be paying above odds. So we would bet against them and make a killing.
I got to the point where I easily made $16,000 each month.
One of the biggest hauls came during the 2010 Super Bowl, when the New Orleans Saints played the Indianapolis Colts. The Colts were favored to win, but my partner was a Saints fan, so we set up the odds against what Vegas was recommending, which generally you shouldn’t do. Everyone who wanted to Colts to win bet against us, but the Saints won. We made close to ten grand that night. Of course, there were also times we had a bad night and lost all our money.
We spent nights counting our stamps, but needed a way to hide them. There were Now and Later candies for sale at the commissary, in those six-inch packages. We’d buy them, take out the candy, trim the stamp books into squares, fold them up, tuck them into the packages, and seal them back up. One package could hold a hundred books of stamps.
We lived well, never calling home for money. We spent maybe $1,500 a month on food, cigarettes, and gambling. Instead of going to the chow hall three times a day, I could prepare a meal in my cell with food from the commissary. I could also pay people to steal special food from the chow hall: shrimp, steaks, roast beef. I’d buy cartons of cigarettes that others had smuggled in and sell them and make a profit. If I liked the shoes a guy was wearing as he walked off the bus, I could buy them from him.
When I was released, in 2014, my probation officer told me she didn’t want me to be involved in gambling, and forced me to shut it all down. That, unfortunately, was the end of my run.
