Getting $$ in the Clink-Clink

Not that braggadocio is my thing or that anyone will even believe me, but I’ve made at least 5,000 stamps gambling on football over the years.

The average Joe, Dick, or Suzy cannot even fathom the thunderous boredom of jail. We have so many toys that provide us constant amusement and live in such a climate of non-stop interaction on the swanky-pants computer-net phones all day that the transition to jail can be quite the mental jolt. I imagined I felt a phone vibrating in my pocket for years… The day-to-day life at the prisons I’ve frequented is akin to an 8-year-old’s two-week long summer camp dream. I can’t lie—it has the potential to be halfway enjoyable… Just hangin’ out with a buncha dudes playin’ sports and games, eating, watching TV, beatin’ meat, yellin’ at our moms on the phone, taking long, hot showers and, of course, gambling on anything imaginable.

When you first go upstate a number of seasoned prison vets will tell you what to expect and give the same advice time and time again. Now, I’m at the point where I’m able to carry on the tradition: Don’t mess with drugs, don’t fuck with homos, and don’t gamble. Initially, they are easy guidelines to follow, but the boredom often causes us to make poor decisions.

The hysteria of March Madness takes me back to of one of my favorite jailhouse activities. Not only will inmates fill out brackets, we’ll bet on every game balls out. We normally bet stamps, but that gets old, so we put pushups on the line or other, more unconventional types of punishment, i.e. dying cockroaches or Jane Fondas, aka monkey fuckers or female pop performer dance routines. Most of the time these forms of debt are paid “on command,” which means that in the middle of the yard or in the messhall, the winner can ask for a performance. It’s all fun and games for the most part.

Not that braggadocio is my thing or that anyone will even believe me, but I’ve made at least 5,000 stamps gambling on the NFL over the years. Every season I usually bank about 1,000, which is pretty huge money in the state prisons where most heads are broke. We do jail-wide football pools every week in which we might make 200 stamps on a win playing against the spread. A couple times I pulled 14 or 15 wins out of 16 and took all that postage! I had a serious talent, or maybe it helps that the majority of the competition isn’t very adept at using logical deduction or conducting research. Also, to my undeniable advantage, out of boredom I listened to a couple hours of sports radio every day, which I somehow now thoroughly enjoy after a childhood of being tormented listening to those blathering DooDooBrains in my dad’s car.

The best way to make sure you collect the cash is to play “money on wood,” which means whatever you bet you put on the table. Sometimes, a halfway respectable inmate would play “the house” or a bookie who would carry his debt until he got a package. In New York we were allowed to get 35 pounds of food in a package from outside every month, and it was always a sad day when someone was down 100 bucks or so, and his package arrived from his hard-working family only to be given up to pay off a debt… I never gave up food from a package. I strictly bet stamps and bricks (boxes of cigarettes), and I was lucky enough to have money and smart enough to bet wisely, usually.

Jailhouse poker is beyond bonerdome. In most of its iterations, you do not bet unless you’re banking on five aces. It makes bluffing kinda obsolete because basically you’re just gunning for rockets. Dudes love to play with three to five wild cards, so more or less five aces usually takes it. I like playing with maybe two or three wild cards, so on a rare occasion a lousy royal flush might take the pot. Unfortunately, almost half of the time you get rockets, some other lucky loser does too, and he’s going to split that pot with you. I’ve played probably 50 varieties of poker in jail—the creativity of some of the games truly makes them a lot of fun to sit around and play all day for years on end.

For example, one popular game is “hand guns.” In this game the numbers that make up all calibers of handguns become wild cards. So, if you have two twos you have a .22, which means they’re wild. If you’re lucky you’ll have two twos, a three, a five, and a seven (.357), which equals five cards and, BOOM! five aces. Ninety-nine percent of the time, poker is harmless, but occasionally someone who doesn’t have the money will bet reckless and put himself in a hole that he cannot immediately pay off.

There is a distinct danger in gambling. I saw my buddy Gary the Retard get busted and do three months in the box for simply running a friendly poker game. He had poker chips and a master sheet with how much money everyone owed, which meant he got time for orchestrating a gambling ring, or some dumb shit. COs gamble right in front of us all day and night too, so lots of them let us do our thing, but certain COs solely exist to fuck with an inmate’s already shitty day. I always had to keep everything stashed someplace safe out of my cube just in case a dickhead CO decided to do a random search. It makes me puke to remember the look in some of these hypocritical fucker’s eyes when they find some “contraband.”

Even though I had a lot of fun passing the time gambling all day every day, I don’t miss it enough to partake in it out here. I played pinochle for thousands of hours. That was and is my game, but not many people know how to play it in the real world. Guys in jail get on a level of playing games that’s pretty insane, because really who else has five hours a day just to play chess, poker, casino, or pinochle? Or the time to watch ESPN and listen to sports radio for half the day every day? Yeeesh… that was the way to make my time move as fast as possible, but I do not miss it at all.

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