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My Accountant, the High-Stakes Poker Player

Should I be nervous that the guy who handles my taxes bets thousands on poker games? I decided to see Ron Rindone in action.

Illustration: Chris Gash

All that breaks the silence is the constant clickety-clack of chips. Otherwise, the ballroom on the second floor of the Ameristar, a casino and hotel in East Chicago, Indiana, is as quiet as a library. It’s 2:30 p.m., and 80-plus fidgety poker players are settling in for what could be a very long night. 

Only the top 20 percent of today’s entrants in the opening qualifier of this tournament in the Heartland Poker Tour will move on for a shot at the big payout of more than $166,000. Among the hopefuls at lucky table No. 7 is Ronald Rindone, 69, from Prospect Heights. Wearing a Fighting Illini hoodie and sipping coffee from a Styrofoam cup, he strokes his meticulously trimmed white beard, patiently waiting for a hand worth playing. Rindone is considered one of the players to beat.

He also happens to be my accountant. 

Last year, Rindone took second in this contest. He bested nearly 500 contenders—including several professional card sharks—to walk away with a cool $74,400 (before taxes), which he plunked into his two grandchildren’s college funds. 

A few years ago, while sitting in Rindone’s Elmhurst office as he tallied my tax return, I noticed a framed photo on his back wall: There he was, posing in front of a big pile of chips at a Vegas casino, smiling like it was April 16. I found it amusing—and slightly alarming—that the bean counter who shepherded my money could be so willing to gamble his own. 

What was Rindone like at the tables? I wondered. Did he apply the same no-bullshit approach that he used when ferreting out questionable tax deductions? In September, he invited me to a tournament to see for myself.

While eating lunch in a sports bar before his first match, Rindone tells me that his profession definitely informs his poker style. “How would most people describe accountants? ‘They’re conservative,’ ” he explains. “That’s how I play. I’m very calculated.” 

For a longtime number cruncher, applying his math skills to the game is like a mental vacation. And the lofty entrance fees? Rindone, who paid $1,650 to buy into today’s game, considers them investments toward his leisure rather than frivolous bets. 

“I don’t belong to a country club,” he says. “I don’t spend my money on theater tickets. The competition at the poker table is recreation for me.”

A gambling enthusiast for more than five decades, Rindone started wagering long before he ever filled out a W-2. He caught the bug as a teen on the West Side in the early 1960s, when he and his buddies, including my uncle Kevin, would hang around the Gateway, the old bowling alley on North Avenue. Like characters in a Scorsese movie, they’d pass the time shooting pool and placing bets with bookies. 

“On Sundays, we’d meet at St. Angela’s Church, and then we’d go to one guy’s house and play cards in his basement,” he recalls. “Or we’d get the newspapers and figure out what football game we were going to bet on that day.”

Wasn’t that illegal?

“Of course it was!”

He and his pals eventually started a social club, and from 1969 to 1984, they’d gather in a Belmont Cragin storefront, chomping cigars and playing poker a couple of times a week. In the early aughts, the rise of internet gambling (now illegal) and stories of newcomers winning millions at the World Series of Poker in Vegas enticed Rindone to try his hand at tournaments. 

He started winning big at events such as the Seniors Championship of the World Series of Poker, from which he took home almost $7,000 in 2013. But that was chump change compared with his performance in last year’s Heartland, which earned him a seat at the nationally televised final round and made my family accountant an instant celebrity in poker circles. Wearing a suit and tie at a table of schlubs, he even garnered a nickname from the TV commentators: Best-Dressed Ron.

He’s not wearing his sharp duds at this event, but thanks to the big-screen TV in the lobby playing last year’s final match, a few players recognize him anyway. Among them is Craig “the Legend” Casino, 62. (Yes, that is really his last name.) Winner of this tournament three times in six years, Casino issues terse congratulations, politely letting Rindone know that there’s a target on him. 

For the first hour or so, Rindone is practically a bystander, playing just a few hands. In contrast, the 20-something guy to his left plays nearly every hand he’s dealt. 

Finally, Rindone makes his move. I see he’s scored pocket deuces (cool poker-speak for a pair of twos). Stonefaced, he bets a couple thousand dollars. The rest of the players fold, with the exception of a burly young guy who matches the bet. The dealer turns over the three communal flop cards. Rindone’s sitting pretty with three of a kind. He tosses in another five grand. The younger dude matches again. After the next card, Rindone is in even better shape with a full house. He goes all in—and his unsuspecting opponent walks right into the buzz saw. Rindone collects $15,000 in chips.

“A lot of these young guys are ultra-aggressive,” says Rindone when I catch him during a break. “I don’t chase bad hands. What is the expression—the race doesn’t always go to the swiftest?”

As the evening crawls along, players fight fatigue with Red Bull and coffee. A woman offering massages (waist-up only) strolls the floor. Three of the original nine players are out. Rindone, looking as fresh as a newly sharpened No. 2 pencil, has recouped nearly his full stack of chips. 

But a few hours later, his luck plunges south, and he takes some big losses almost back to back. Boom—he goes from winner to loser in a millisecond.

“You can’t win on luck, but you have to get lucky to win,” Rindone says the next day, looking unaffected. 

The night wasn’t a total loss. In accordance with federal law, he’ll be deducting the $1,650 buy-in on his 2016 tax return.

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