When I Was A Donk: With James Calderaro

In this series, Card Player asks top pros to rewind back to their humble beginnings and provide insights regarding the mistakes, leaks, and deficiencies that they had to overcome in order to improve their games.

James Calderaro started his career in the nightclub industry, running several successful businesses before switching his focus to poker. The New York-native was purely a gambler to start, but quickly realized he had a knack for the game.

Now with more than a decade in the game, the 52-year-old has racked up more than $4 million in live tournament earnings. He has made four World Poker Tour final tables, having finished runner-up in both the 2012 WPT bestbet Jacksonville main event, and the 2014 WPT bestbet Jacksonville Spring Open, before breaking through for his first win in the 2014 WPT Lucky Hearts Poker Open.

Calderaro’s biggest score came when he won his first World Series of Poker bracelet, in the prestigious $25,000 buy-in pot-limit Omaha high roller event. The 2017 title was worth a whopping $1,289,074. Incredibly, Calderaro nearly went back-to-back, taking fourth place in 2018 for another $414,134.

Here, Calderaro talks about his experience deep in the 2009 WSOP main event.

“In 2009, I went deep in the [WSOP] main event, the year Joe Cada won it. We were down to the final two tables, and it was a really weird hand that took place. Darvin Moon had all the chips at the time. I had played with him for like three days already, and he had a massive stack.”

“I get dealt A-Q, and Darvin opened with a raise in front of me. I three-bet, and Billy Kopp came over the top behind me all-in. Now, Billy had me covered, but most importantly in my mind, Darvin had him covered. So after Darvin folded, I had to decide if Billy would make that move with a hand worse than A-Q.”

“I ended up folding, and I think it was a big mistake. In my mind, how could Billy make a move like that into Darvin unless he had a monster? Unfortunately, I found out later that Billy had pocket tens, so it was a spot where I should have called and gambled.”

“Instead, I folded and held on to my short stack, and a little while later, I lost a flip to Kevin Schaffel, my K-J to his pocket tens. Who knows? Maybe I would have won the earlier flip and could have made the final table. If that spot came up today, I would definitely be calling. In that situation, with my stack at the time, A-Q might as well have been pocket aces.”

“I ended up finishing 13th, and right after that, Darvin busted Billy in [that big hand] that everyone saw on TV. Darvin went into the final table with a big chip lead and used that to finish second.” ♠