Daniel Conderman 
Nobody looks fondly upon jail. It’s not a place anyone dreams of being. But if you’ve done time, you know that sometimes, in the strangest ways, you find small pockets of enjoyment—moments that, looking back, almost make you miss it. For me, that was poker night.
Now, let’s be clear: gambling in jail is strictly forbidden. It can get you in trouble. But just because something is against the rules doesn’t mean it doesn’t happen. You just have to be creative. The system we had in place was simple but effective, and the stakes were just right—enough to keep it interesting but never enough to cause real problems.
The key? Decks of cards. Commissary sold them in two colors: red-backed and blue-backed. One color was for play; the other was for markers. If you were paying attention, you could see who was in and get a rough idea of the action. If you wanted in, you’d sit down, tap the guy next to you, and if he gave you the nod, you were golden. Just like that, you were in the game.
Buying in was easy. Jail allows you to have up to $20 a day in dollar coins for vending machine purchases. That meant the money was already in circulation, and it was easy to move right under a guard’s nose. You’d see a guy hand another a few coins with a simple cover: “Hey man, thanks for the soda and chips.” Just like that, the transfer was done. Nobody batted an eye.
Cashing out was a little trickier, but the system worked. If you were up and your release date was approaching, there were always a couple of guys who had “walking-around” cash—$100 or so stashed in their outside lockers. With a little coordination, your winnings would be waiting for you on the outside. A quick handoff during the day, a transfer from a friend’s bank account, and within 24 hours, you had real cash in your pocket. A full payout, clean and simple.
Texas Hold’em was the game of choice. The guards, blissfully unaware, saw nothing more than a group of guys passing the time with cards. As long as nobody got loud, nobody cared. The accounting for this underground empire? Hidden in plain sight. A notebook filled with one guy’s treatment program homework—pages of scribbled assignments, therapy reflections, and buried among them, the real business: a ledger tracking every chip, every marker, every debt and payment.
It was a small thing, but it made the time pass. It gave us something to look forward to, something to strategize over, something to master. It was a taste of control in a place where control was rare. And as strange as it sounds, when I think back on jail, I don’t miss the walls or the rules or the boredom. But I do miss the cards.
And that’s just one of the things that ruled about jail.
Stay tuned for Volume 2.
