That Time I Bluffed Leonardo DiCaprio

post first published in my poker posts on Quora

One of my poker stories stands out. It was back in 2004, the year after everyman Chris Moneymaker pocketed $2.5 million winning the World Series of Poker Main Event, forever changing the culture of the game in the process.

By winning a cheap online satellite tournament (these events are common and equate to a qualifying event), Moneymaker secured his seat in the $10,000 No Limit Hold’em 2003 WSOP Main Event for the bargain price of $25. This proved once and for all that anybody can win big at poker.

Moneymaker in 2003

Over the course of the next year, poker rose from obscurity to hit the mainstream. Every casino opened a card room. And the rooms in the pre-existing meccas of poker, like Bellagio in Las Vegas, were full of people from all walks of life, including even Hollywood elites. 

I’d been hired by the Casino de Montreal to deal Blackjack a few years before these events, an amazing opportunity for me at the time. After working through high school for $6-$8/hr, I still remember the thrill of being twenty and commanding a stable $17/hr wage. 

Despite the decent job, I'd been playing poker regularly in the Montreal underground with the aim of making extra money. By 2004, I’d quit working as a dealer and was an up-and-coming pro with a modest bankroll of $20,000. My next move was to put that bankroll on the line to take advantage of an historically soft game, featuring one of the world’s biggest celebrities. 

To set the stage, I walked into the Bellagio, and it’s late, and I see a high stakes No-Limit Hold’em game in the back. This was normal, but today there were several people hovering around the table, many of the them young women. And one of them was Paris Hilton! I approached the floor man. 

“What’s up with the game in the back?”, 

“Oh, Leonardo DiCaprio is playing in that game. Do you want on the list?”

Normally I prefer Limit Hold’em and only rarely play the riskier and far slower-paced No Limit version of the game. That night was different. If I played, I might get to play with a famous person, and one day, maybe, just maybe, get to write about the experience on Quora, because an anonymous person asked me if I had a good story. It was a chance I couldn’t pass up.

♠

I put my name on the list and to my surprise I was seated fairly quickly, one seat to the right of Leo. I was three feet away from one of the biggest stars in history. We could’ve given each other coronavirus. 

The question now was, could he play cards? 

I was sitting with $5,000 in front of me. As I previously mentioned, I had only $20,000 to my name. It was entirely possible that Leo could completely break me over the course of a few hours. My mindset was far from being starstruck. It had to be. I was thinking, “how can I take this pretty boy’s money! Lord knows he has enough to go around!” Thankfully, I did manage to get him good in one hand. 

I still hadn’t tangled with Leo after several hours of play. We were in plenty of hands together, but we both seemed to be getting blown out of the pot by a few players across the table who’d adopted a betting style that could best be described as being like a machine gun. And then a hand finally came up… 

There was one caller before one of the wild bunch raised it to $100. I was on the button, and so last to act, and decided to raise the pot with the aim of eliminating everyone but the raiser. I made it $200. To my surprise, Leo, a player who’s style could best be described as weak/tight —meaning he rarely plays a pot, and when he does, he rarely invests much—, who was in the big blind and so in terrible position for the rest of the hand, opted to call. This was, scary. The other players called as well. There was a little over $800 in the pot. 

The flop was QQ2. The first and second players checked. I made it $800 to go, a large bet designed to take the pot right there. Leo mumbled something about how I must have the Queen, and then called the bet cold. I was concerned to say the least. However, I now had good reason to believe that he didn’t have the Queen. The thought entered my mind that he could be playing me. He is regarded as one of the best actors of our time, after all. 

The next card was an irrelevant 6. He checked. This was my time to go with my gut and prove that I was playing half-decent No-Limit Hold’em. I again made a large bet, $2,000. The pot was about $4,500 at this point. Leo went into the tank (poker parlance for thinking for an extended period of time). 

He looked at me and looked around the table and said, “he must have the Queen…” As he folded, he also stated that he held a good pocket pair. I still held my cards and laughed… He looked at me. 

“Show them then.” 

“You sure you want to see them?” 

“Sure”, he replied. 

And that’s when I rolled over the T9 of spades. I had absolutely nothing. 

I received approving looks from the other players for the rest of the night. Leo ordered crab cakes from room service. He was a great sport and also seemed like a genuinely good person. Just not as good an actor at the poker table as he is on the big screen.