In life, simply saying please and thank you are freerolls; they cost you nothing and may very well benefit you in kind treatment from others.
With poker, whether at brick-and-mortar casinos or in online casinos, freerolls are more clearly remunerative. If you don’t believe me, just ask Chase Bricker or Pablo Brito.
Bricker won $1 million in Las Vegas in the ClubWPT Gold Invitational freeroll, and just a few days later, Brito pocketed $200,000 in the Bahamas at the WSOP Paradise freeroll.
Among sharp gamblers, Bricker and Brito are not alone. In my upcoming book Advantage Players, I write about Eddie Teems, a seriously talented advantage player who has capitalized on freerolls to win cars, houses, and lots of cash.
I’ve worked my way into a good handful of freerolls. I never won a car or a house. But, essentially, I did win a pre-K education for my oldest of two daughters.
Nineteen or so years ago, I was in Las Vegas to cover the World Series of Poker. Giving reporters a taste of what it is like to compete in a top-notch poker tournament, the WSOP folks put together a media event. The entry fee of the Texas Hold’em tournament was zero dollars, making it a freeroll, and the winner received $10,000 that was earmarked for charity.
I played and got off to a good start. Then my buddy, the late comedian Norm Macdonald, lost an all-in to me. He walked away with a smile, looking to play some real money poker, while somebody muttered something about chip dumping. I do not think he did it. But who knows? He was an awfully nice guy and I don’t doubt that he wanted to get to that bigger game.
One thing for sure is that I quickly became a frontrunner. My luck held up and I wound up winning the whole thing.
Tournament supervisor Matt Savage asked what charity I wanted the $10,000 to go to. Shamefully, I did not have a ready answer.
I suggested that he let me use the windfall for a WSOP main event entry. I promised to give half of what I might win to charity.
“Right,” he said. “You want to parlay it.”
“Yes!” I told him, enthusiastically.
“No,” he replied, clearly having heard this argument before. “The $10,000 has to go to charity.”
Fine. But to what charity? I considered Greenpeace, the ACLU, the synagogue my parents belong to. Then I remembered that I was in the middle of hustling to get my daughter into a good public-school’s pre-K program.
If you don’t have kids, pre-K is a year of school before kindergarten. In New York City, where I live, getting into public – i.e., free – pre-K is via lottery. Kids who don’t get lucky have parents who spring for private pre-K, blowing $20,000 or more.
Matt gave me a couple days to figure out where I wanted the money to go. I called our first-choice school, offering a $10,000 donation from a poker tournament for guaranteed entry.
“We don’t do that sort of thing,” I was snootily told.
The second-choice school was more open minded. The admissions person wanted a day to consider it. She got back to me in 20 minutes with word that I had a deal. I asked that the money get spent on video cameras and laptop computers. I was promised that it would happen.
Matt ferried casino money to the school and my daughter got in. She had a great experience. I saw exactly one laptop and one video camera out of the donated funds, though.
Respecting their hustle as much as they apparently respected mine, I didn’t say a word. Instead, I smiled whenever I saw the teacher take out the camcorder, videotape her class reciting their ABCs, while perhaps lingering for an extra few seconds on my daughter’s face.
Michael Kaplan is a journalist based in New York City. He is the author of five books (“The Advantage Players” comes out in 2024) and has worked for publications that include Wired, GQ and the New York Post. He has written extensively on technology, gambling, and business — with a particular interest in spots where all three intersect. His article on Kelly “Baccarat Machine” Sun and Phil Ivey is currently in development as a feature film.
*Photo by World Poker Tour
