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Every night, there’s an off-the-books poker room operating somewhere in Chicago. It’s been going on since before Nelson Algren wrote The Man With the Golden Arm, a novel about a junkie musician who deals cards in the back room of a Wicker Park tavern. Some guys wanna play poker in their native language—the Koreans and Assyrians have regular games. Some guys are a little short this week—unlike a casino, your friendly neighborhood cardsharp will extend credit to keep his tables full. And some guys have been banned from the Horseshoe for drunk and disorderly conduct.
To get into a game, you’ve got to know someone. I’m headed to a Southwest Side poker room with a professional gambler I’ll call the Diplomat. The Diplomat makes his living playing poker.
“I was in a game where everyone had a gun,” the Diplomat tells me. “I was winning so much I started to get nervous. But they walked me to my car to make sure I didn’t get robbed. They were really nice guys. That’s the only time I’ve ever seen weapons.”
We walk, unarmed, to a storefront that still has the sign of its past tenant—a coffee shop—hanging over blacked-out windows. Buzzed in through a door marked “MEMBERS ONLY,” we pass a security monitor and enter the manliest cave in Chicago: two tables full of guys in Bears, Fighting Irish or White Sox caps, fondling their chips and watching the NBA playoffs on flat-screen televisions. The only women in the room are the dealers and the waitresses, who bring around free beer and Italian beef sandwiches.
I buy $200 in chips from the host, Tommy, and start losing to a dude wearing sunglasses and a bandanna, who takes poker inscrutability to the Invisible Man level. When my stack reaches $150, I interview Tommy.
“How do you keep the cops from busting this place?” I ask Tommy, who has been showing off a Social Club license that will allow him to collect membership fees from his 600 regulars.
“I hire an off-duty police officer to work the door,” he says. “I sponsor their softball league. Cops get a $25 chip. There’s three CPD in there now.”
“Gambling doesn’t bother cops,” the Diplomat tells me later. “A room will only get raided if it’s ripping people off with a 15 percent rake.” Tommy takes five, same as a casino.
Before I walked in, I knew Texas Hold ’Em only as Gabe Kaplan’s TV gig after Welcome Back, Kotter. Back at the table, I am learning that poker is uncomfortably like business or politics: Guys with money steamroll everyone. I lose a hand because I don’t have enough chips to scare a young Albanian named E-Dog out of a pot. Down to $55, I make my last stand with an up-down straight and flush draw. The straight and flush fail to fill, and the Invisible Man beats me with queens.
“You had a great hand,” the dealer consoles me.
The clock strikes midnight as my balance strikes zero. Tommy stays in his club until the last gambler leaves—sometimes eight in the morning, if a profligate millionaire named Drunk Stan is at the table. (“I charge people $100 to play him.”)
“Damn, I saved a lot of money by losing $200,” I tell the Diplomat on the way home. “If I’d won, I’d be back at that place every week.”