True Tales From A Hollywood Poker Hustler: Side Bets With Poker Pros, Con Men, And Movie Stars

In my last column I talked about a prop bet TV pilot I produced that never aired starring Phil Hellmuth. This time, I want to continue on my mini prop bet series by sharing a couple of the crazy bets I’ve made, won, and lost over the years with celebs and pros alike.

One thing I find most fascinating about the prop bet experience is how it brings out a “buddy’ vibe in just about all those who partake. And let’s face it… sometimes it’s just fun to watch your buddy writhing in pain from the loss of a side bet while at the poker table.

Case and point: I’m at The Commerce Casino in a $25-$50 no-limit game along with Antonio Esfandiari and his good pal Phil Laak. Everyone who knows Antonio and Phil understand what I’m talking about when it comes to the satisfaction derived from seeing a good friend suffer after losing a stupid bet that he shouldn’t be making in the first place.

Antonio had been egging on the Unabomber all night to make side bets, but hadn’t had any luck. Finally, Antonio says, “Houston, do you think Phil has the balls to do a coin flip with you for $25,000 in cash?”

Note: Phil and I both had about $25k in cash on the table along with our chips. I asked Antonio why he wanted “me” to do the flip instead of himself. Antonio exclaimed that he would simply take immense satisfaction in watching the Unabomber go catatonic with regret when he loses to me because I didn’t often play in the casinos and would make the odds of Phil getting his money back from me that much higher.

I had zero edge, and knew it was a stupid gamble, but hey… we were having fun. Cocktails were coming, and cards were being chased. So I said, “Sure, red or black on the flop Phil?”

Phil picked black. The flop came out with one black ace in the window… followed by a 5 and 7. Phil, who had been jovial, laughing, cutting up, and telling jokes all night, suddenly changed. It was as if the life had just been sucked out of him all at once.

Meanwhile, Antonio took immense pleasure in grabbing the $25k brick of cash in front of Phil and casually tossing it over to me. Phil just stared out into nothing as Antonio yelled, “Look at him… look at the regret! You just crushed his soul!” while the entire table laughed along and cheered with delight.

I could only imagine what the instantly depressed Phil Laak was saying to himself. “Why??? Why do I always let him talk me into this shit?” But it was too late. The money was mine, and Antonio got just what he wanted, a good laugh at his friends’ expense.

And Antonio never let up after that. The rest of the night he kept making comments about how Unabomber was so good at making wise decisions at the poker table. Each comment only stuck the knife in a little deeper.

Of course, that was pure gambling, but sometimes a side bet can be made as a dual incentive. Like the time I made a $100,000 weight loss bet with a character by the name of Big Al. Mike Sexton recently reminded me how Big Al played such a fun role in my Hollywood poker game and was surprised I didn’t write about him in my book, Billion Dollar Hollywood Heist.

When he brought it up, I was pissed at myself because Sexton was right. Big Al, the tall Vegas gambler who was involved with Doyle’s Room, among other things in the poker world, was in fact a lot of fun to play with.

The conditions of this six-figure bet were simple. I had six months to lose 40 pounds of weight I had put on after having a back surgery in 2006. We brought in the scale, and even did an official weigh in.

About two months later, Al was back in town and we were hanging out at the hot new club Villa that became famous when Leonardo Dicaprio showed up on its opening night. A few others and myself were investors in the club and it was a fun place to hang out before or after the game. I had starved myself to lose 20 pounds by that time, but I lost it in the first month and had been at a complete stand still.

But since Big Al lived in Vegas and only played on occasion, he hadn’t seen me since we made the bet. When I saw him, I bought him a drink and got to work. I started thanking him for encouraging me to get healthy. I told him how I hadn’t even started trying until a few weeks ago and was already down over 20 pounds. I reminded him of what he said when we first made the bet, which was, “I don’t even want to win. I just want to see you get healthy.” And then I thanked him from the bottom of my heart.

Then, as if it were on the shot schedule for a major Hollywood film, Al stepped up and offered, “I’ll buy out of it right now for 10 grand!”

I quickly agreed to the deal, which of course felt like a major win considering my weight loss had already plateaued and I was a big underdog to complete the bet. That’s when Al broke the news to me that he would have settled for $20k! I guess if felt like a win for both us, which is definitely not the case for this next side bet story.

Around the same time as my weight loss bet, I also had a long running side bet going with Tobey Maguire. Tobey and I prided ourselves on seeing who could win the most sessions in a row without a single loss. I had just come off a $3 million dollar winning streak with no losses when we decided to do a modified version of the old “last longer” wager. The bet was $25k to see which one of us could win the most times out of 10 sessions.

This little side wager brought out our competitive spirit and would prove to be a great bet for both of us in the long run… although I think Tobey ended up enjoying it much more than he should have. I remember Molly Bloom asking me why I cared so much about a $25,000 side bet with Tobey when he and I were winning hundreds of thousands of dollars per session every time we played. I explained that it wasn’t about the money, it was about enjoying a little bit of the old, bust-your-buddy pride that didn’t come along very often, and being able to rub it in his face for an eternity.

And believe me, Tobey was keen on the rib jabs even more than I was. With Tobey, a bet was never quite that simple as he was a stickler on setting all sorts of small parameters that would obviously be in his favor. For instance, he liked to show up late to the game and always left at a certain time. I, on the other hand, would show up early enough to see the first hand dealt and if the game was good I would play until the sun came up as long as I knew I was getting the best of it.

Knowing this, Tobey made a rule stating that a win or loss was only valid during the time he arrived, and the bet had to end when one of us quit for the night or by 11 pm, whichever came first. He knew that I would always play longer than him, so If I happen to be down one night when he decided to leave, even if I won by the end of the session, it would only count based on whether I was up or down when he called it a night.

I countered by proposing that if I was down before he showed up to the game, my total would start from the amount of chips I had on the table as opposed to how deep I was on paper. I also negotiated a minimum stop time of midnight which he countered on as well. He gave me till midnight to play if I was stuck, but negotiated a stop time by 11pm for himself if he wanted to quit early. Of course, I could stop at 11 pm too, but he knew that I would rarely stop that early.

The first time we did the bet I won nine sessions in row to Tobey’s eight, winning me an extra cool $25k and bragging rights for at least the next 10 sessions while we repeated the bet again. At week 10 of the second $25k side bet… it was a close race!

By 9 pm Tobey was up over $200k and decided to sit on his chips until his clock ran out at 11 pm leaving him, with a win rate of nine out of 10 sessions. I had won eight and was stuck, but still had time on the clock to make it a tie!

Tobey decided it would be fun to stick around and try to distract me from getting even until my clock ran out at midnight. Thankfully, by 11:45 pm I entered a huge pot with 8-8, flopped a set and went from being stuck $125k to being up $48k for the session.

I took a break and was determined to call it a night. A tie would be fine by me! Tobey seemed to be a good sport, shook my hand, and started talking about how it was a shame for both of us to quit while the game was so good. Then he pointed out that cards were still coming to me and I was on the button.

I sat back down, checked my hole cards and was staring at A-A. In my mind, we had already agreed to a tie and even if I ended up stuck at the end of the night, the bet was locked in! There were two limpers and a $10k raise before the action got to me.

I popped it up to $50k. One call, one fold, and now the original raiser was going into the tank. It was Bob Safi. Bobby had cracked my aces for six-figure pots so many times in the past it would take both hands and at least one foot to count them all.

Then Bobby says, “So Tobey, this bet between you and Houston, what is the rule if he’s involved in a big pot when the clock strikes midnight?” And that’s when my heart sank.

We had determined that totals were calculated based on what you had in front of you, not what was in the middle during a pot. But I didn’t think I had anything to worry about because it had to have already been past midnight when we started playing the pot. I looked at my watch. Then, in disbelief, I looked at my phone! Sure enough, it was 11:58 pm. Which means that if Bobby stalled me on his call until after midnight, I would lose the bet with Tobey.

I now know what had happened. Tobey was waiting around just hoping to get me into a position where he could distract me and win the bet. Not only did Bob wait until 12:01 but then he called. The flop came three hearts. Of course, I had the A A.

Bobby pushed for the rest of his stack. I had him covered, but I would only have about $10k left if I lost. You can never tell with him, so I called. He was on a draw… and of course he peeled it off right on the damn turn like he always does. I went from being up about $50K to being down over six figures, as well as losing the additional $25k to Tobey. Much like Antonio was with Phil Laak, Tobey enthusiastically celebrated his side bet victory while I stared at the felt with steam coming out of my ears.

Have you ever made a prop bet or side bet with a friend that got overly competitive? If so, I would love to hear about it. Leave a comment on my Facebook, Twitter, or YouTube channel.

Also be sure to visit my website or watch below for this week’s supplement video where I’ll be sharing more about the I’ll Take That Bet pilot hosted by Phil Hellmuth, as well as featuring one of the greatest side bet card hustles of all time performed by the late, great Ricky Jay. Not only will you see Ricky hustle numerous people in what seems to be a pretty straight forward showdown, but at the end of the video you’ll have the opportunity to learn exactly how he did it from yours truly!

Thanks for reading my column, I hope you all have a great week at the tables whether it be a home game, online, or in Las Vegas with giant plastic walls between you and the next guy. No matter where you play or who you play with just remember… stay sharp! Stay Kardsharp!

Houston Curtis, founder of KardSharp.com and author of Billion Dollar Hollywood Heist has lived a successful double life as both a producer and card mechanic for nearly 30 years. His credits include executive producing gambling related TV shows such as The Ultimate Blackjack Tour on CBS, The Aruba Poker Classic on GSN and pioneering the poker instructional DVD genre with titles featuring poker champion Phil Hellmuth.

Barred for life from Las Vegas Golden Nugget for “excessive winning” at blackjack, Houston is one of the world’s most successful card mechanics and sleight-of-hand artists of the modern era. Curtis, who rarely plays in tournaments, won a 2004 Legends of Poker no-limit hold’em championship event besting Scotty Nguyen heads-up at the final table before going on to co-found the elite Hollywood poker ring that inspired Aaron Sorkin’s Academy Award-nominated film Molly’s Game.

Curtis resides in Phoenix, Arizona where in addition to running a production company and independent record label, he is also a private gaming/casino protection consultant to clients across the globe seeking insight into master level card cheating tactics via advanced sleight-of-hand technique. To reach Houston for a speaking engagement, consulting or production services send email to [email protected].

All views expressed in this article are those of the author and do not necessarily reflect the views and opinions of Card Player.