Why I Love My UES Poker Game

If you live long enough in Manhattan or any other part of the city, you learn to accept upheaval. Not mere change. I’m talking about a bank replacing a Gap, which replaced a Shakespeare & Co. book store, which replaced a used-record shop, which replaced a coffee house in the first place. And probably all of that tumult taking place in — what? — five years?

That’s one of the reasons I like to hold on to what has endured, a favorite coffee shop or a bodega or a bakery. Or, for that matter, my weekly poker game.

I have been playing in the same game on the Upper East Side for 23 years. Funny, in college, when my disreputable buddies played hands of table-stakes poker literally all night, I never participated — and not only because I was cheap and I knew I had no chance of making any money. I’d get back to my dorm and there would be six or seven of them going at it from dusk to dawn. Thank God, I had my work at the college paper to keep me occupied or I might have succumbed and lost my shirt (both of them).

What made me join the Monday night game in 1995, then? I could talk about peer pressure — my editor at Bloomberg had perfected the art of gentle persuasion. Many of the players were my Bloomberg colleagues so I would be among friends. And it sounded like fun. I figured I’d play for a year and then have material for my Mediocre American Novel.

People like to say that you can take the measure of people’s character by confronting them on the tennis court. I disagree. I’d transfer the setting to a poker table. More is at stake. And not only money. Can someone bluff effectively? Can he or she take your last ten bucks with a smile? In poker, as in life, fear of success can be more debilitating than fear of failure. You need a killer instinct to play poker well. Sentiment is someone else’s problem.

I also immediately liked the guys at the poker table. Those who weren’t Bloombergers had worked in Europe as reporters and editors. One black sheep worked in advertising. Another was a psychologist. I would have feared his ability to read my mind but I couldn’t help but notice that he looked just like Al Goldstein, the adult-magazine king, so I laughed more than I cringed at him.

My first year was a rocky one. I lost money every night. I was in way over my head and I knew it. We’ve always played a high-low game and I once was dealt a 6-5-4-3-ace hand in five-card draw — virtually unbeatable. But I was so intimidated that I insanely folded it when one of the guys raised my bet. (I’ve gotten much better over the years).

My favorite all-time hand occurred about 10 years ago. We were playing a round of seven-card draw: that means you get three cards down and four cards up and you can use five of them to go high or low (or high and low). The round starts out with each player getting two cards down and one up. I was dealt three aces, a virtual statistical impossibility. Then I got a deuce and a three and a six. I raised every bet and glowed inwardly. So, the players assumed I would be going “low.” For the fourth card, which was also dealt down, I got — you guessed it! — the fourth ace. Four aces!! A miracle.

We all declared high. One guy had three queens. Ha! Another boasted a small full house! Double ha! Then, Charlie, the best and toughest-minded player at the table, fixed his death-ray look on me, and smiled: “Sorry, Jon. Four jacks.”

I said, “Sorry, Charlie. Four aces.” As they had all gone high, I won the entire pot — roughly fifty bucks. It was truly one of the great moments of my life.

Sadly, our game is slowing down. A few of the guys have hit the age of ninety and they don’t get around so easily. When it snows, they understandably don’t want to go outside.

You probably know someone who plays in a game like this. I hope you have the good fortune to play in one.

It’s like a little clubhouse. Women, of course, are welcome — as long as they bring their money — and we’ve had several competing over the years. But week after week, you’ll generally see six or seven men sitting around a cramped table, with a frayed green felt covering. It’s an eclectic group of retirees (one of whom, who shall go nameless, is a broadcasting legend), freelancers and the occasional poor sap who has to get up in the morning to go to work and frets about the reliability of the Q train.

Usually, the big winner takes home north of a hundred bucks. I have — ahem — the table record from the night I pulled in $278.

Honestly, I do tend to win most nights. I’d be a fool to play for the rent money. I like to match my wits against the others in what is actually a pretty serious neighborhood. I relish the opportunity to talk about sports and movies and politics for four-and-a-half hours. I like the other guys.

Play to win. But considering the fun I invariably have, I never really lose.

Jon Friedman, who most recently wrote about Michael Wolff and Paul Simon in these pages, teaches journalism courses at Hunter College and Stony Brook University