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A Poker Life: James Calderaro

by Julio Rodriguez |  Published: Apr 30, 2014


James CalderaroJames Calderaro doesn’t look like the most likely candidate to be a breakout tournament star. After all, the 48-year-old New York native spent the early part of his working life in the nightclub industry. However, his consistent results over the last 12 months suggest otherwise.

By putting together a string of successful cashes on the tournament circuit, Calderaro has transformed himself from a gambler into a bona fide poker pro. Since May of 2012, Calderaro, who now resides in Florida, has made four final tables, including three runner-up finishes and one win.

In total, he has brought his lifetime tournament earnings to just under $2 million and sits in 15th place in the Card Player Player of the Year race.

Poker Beginnings

James Calderaro was born and raised in Long Island, New York. He spent his early working years in the automobile business, running transmission shops before making a move south to the gulf coast of Florida.

“I started off as a bartender, bus boy and waiter,” he recalled. “The hospitality industry in Florida was huge. Eventually, with some partners, we opened up a club called the Calypso Bay Café in Clearwater, Florida.”

Despite running a successful club, Calderaro never strayed far from gambling. Though he learned poker at an early age and played with relatives, he was more interested in sports betting or putting some money down at the dog and horse tracks. But in the back rooms of the club, Calderaro and his buddies would often sit down for a game of cards.

“We would beat up on each other, even though none of us really knew what we were doing,” he said. “Back then it was mostly gambling. Very little poker knowledge was actually being used.”

After four years, Calderaro and his partners sold the club. Though he had a couple smaller clubs to run after that, Calderaro opted to make a bold career jump into poker.

“I had a lot of other offers to stay in the business, but to be honest, I burned myself out in that scene,” he admitted. “It was a lot of work. If you want it to be great, you have to do it day and night. It’s not as glamorous as everyone makes it seem. We were lucky enough to be successful our first time out, but poker felt like a lot less stress, believe it or not.”

Finding Early Success

Florida’s poker laws limited cash games pots to just $10 when Calderaro began taking the game more seriously, so he was forced to play in the much bigger private home games in the area. He did that for years before tournaments piqued his interest.

In 2008, recording only his second ever tournament cash, Calderaro finished 20th in the $25,000 buy-in World Poker Tour Championship at Bellagio for $105,525. He was just getting his feet wet with tournaments, but Calderaro wasn’t fazed by playing in one of the most prestigious tournaments of the year.

“I guess I was a little ignorant, because the magnitude of that tournament really didn’t sink in and affect my play. Obviously, I’m a lot better player today than I was back then, but I wasn’t star struck by the players or anything like that.”

The next year, Calderaro entered the World Series of Poker main event and played his way to a 13th-place finish, good for $633,022. Despite coming so close to becoming a member of the November Nine and joining the likes of Phil Ivey, Jeff Shulman and Joe Cada at the final table, Calderaro wasn’t disappointed by his exit.

“That was an incredible feeling,” he remembered. “I still think that’s my biggest accomplishment, even after winning a major tournament. I was basically one hand away from making the final table that year, so people are always asking if I was disappointed by finishing 13th. I really didn’t see it that way. I was short stacked for basically the entire tournament, so in my mind, I was very satisfied to get that far.”

In 2010, after a deep run in the PokerStars Caribbean Adventure High Roller, Calderaro took third in the WSOP $10,000 Pot-Limit Hold’em Championship for another $284,845. He final tabled the Venetian Deep Stack Extravaganza main event to cap off another successful summer.

A Successful Partnership

Though Calderaro had real estate investments to focus on, 2011 was a bit of a dry spell for him. Outside of another deep run in the WSOP main event, it was his worst year on the tournament circuit. Then in 2012, he turned it all around with a second-place finish at the World Poker Tour bestbet Jacksonville $5,000 main event for $236,560.

In December, he met his girlfriend Lily Kiletto, a former cash-game grinder turned tournament player. Together, the two of them began traveling the circuit in search of success.

In February of 2013, Kiletto took second at the WPT Lucky Hearts Open in Hollywood, Florida for $191,880. In October, Calderaro took second at the Heartland Poker Tour stop at Daytona Beach Kennel Club for $64,158.

Then in February of 2014, the two returned to Hollywood for another shot at the WPT Lucky Hearts Open. Incredibly, both made the final three tables with Kiletto bowing out in 19th place. Calderaro made the final table along with notables such as Keven Stammen and chip leader Shannon Shorr.

“We were getting sick of second,” Calderaro said. “I didn’t want to finish second again. Not only because I had finished second at my last WPT final table, but also because Lily had gotten second in the exact same tournament a year before. So I felt the pressure to win.”

Incredibly, Calderaro made it to heads-up play and topped Shorr to earn his first WPT title and the $271,103 first-place prize. The win was even more satisfying after discovering that his play had been criticized on the live web stream commentary.

“I think my game, especially at that final table, is a little misunderstood,” he said. “I’m definitely a feel player and I’m really proud of that part of my game. Some guys are all about the math, but I’m going to let the history I have with a player determine what decisions I make. Each individual and circumstance is obviously different, but for the most part, I’m going to find a pattern and then change the way I play to take advantage of it or throw someone else off. It might not always make perfect sense to someone else watching the table, but it works for me.”

Moving Forward

Calderaro and Kiletto continue to travel the tournament circuit. Although he hates living out of a suitcase, she loves it and he plans to follow her until she can join him in the winner’s circle.

The two spent March proving that they are one of the game’s strongest power couples today. Calderaro took 10th at the WPT Rolling Thunder for $30,170 and Kiletto took yet another second place at the HPT Agua Caliente for $55,607. Then they went back to Florida, where Calderaro finished runner-up yet again, this time for $133,764 at the WPT bestbest Jacksonville Spring Open.

Though both players have found themselves in the spotlight over the last year, Calderaro prefers that Kiletto get all of the attention.

“It’s all about the cash for me,” he said. “I’d rather Lily get the camera time and interviews, because that’s what she’s playing for. I like winning, but if second place paid more than first, I’d have no problem with losing.”

Regardless, Calderaro is putting the rest of the poker world on notice.

“Look out, because here we come.” ♠