For anyone who's read my book [Billion Dollar Hollywood Heist] or watched Molly's Game, then you know that in real life, the game had Leonardo DiCaprio in it, and obviously Toby McGuire.
Toby and I had put together this master plan to have the biggest game in Hollywood with him being a huge draw. And obviously we wanted Leo in.
One of the funny things is, the night before Leo came to play, Toby pulled me aside, and he said, "You know, we've got to stake Leo". I was like, "Stake Leo? What the hell are you talking about?"
But, you know, Toby pointed out, once you get to Leonardo DiCaprio status, you're freerolling in life. The good news is it wasn't that big of a risk because Leo was the tightest player on the planet. He played nothing but aces and kings. We staked him, and he did fine, and people would lose 100 grand just to say they sat with the guy for a night.
A few months later, Toby had asked me to meet him over at Leo's house – they had these houses close to each other, up in the Bird Streets in Hollywood Hills.
So I show up to DiCaprio's house, and for whatever reason, Toby wasn't there yet. And Leo says, "Hey, come on in. Would you like to tour the house?" It's like getting my own private Lifestyles of the Rich and Famous tour.
And he starts pointing out all this furniture in his house. He said, "You see that sofa?" Yeah. "You see the couch?" Yeah. What about it? He said, "So I've got this deal going with Giorgio Armani. All I've got to do is wear an Armani suit to three different events, and he's going to come in and put custom Armani leather on all my furniture in my entire house."
And he was cracking up about it, and I remember thinking, Toby was right. Once you are Leonardo DiCaprio, the most talented, wealthiest actor in the world, apparently, you don't have to use your own money for anything anymore.
DiCaprio: Aces cracked
So cut to a year later. Now our game is off the rails, and we're playing at the Four Seasons, and the stakes are high. There was one night where the game was kind of overbooked, and I had a meeting that night downstairs in the lounge of the Four Seasons, and Toby kept busting my balls, saying, "If you get up, you're going to lose your seat."
And Leo showed up, and he was wanting to play. I was into the game for 100 grand, but I was up 100, so I had $200,000 in front of me. So I started thinking, "How do I keep my seat in this game and still take this meeting?" And that's when it dawned on me: Leo had played much lower stakes when Toby and I were staking him. And then I remember the Giorgio Armani leather upholstery freeroll, also remembering that he only played aces and kings, so I felt pretty safe.
I said, "Leo, do you want to play over and just play my chips? I'll be back in like 30 minutes."
I figured that would be just enough time for Leo to get his fix in and play some poker. So I go down and I have my meeting, and I come back up, and the first thing I do is look over at the table. Leo's not there.
And then I walk over and I look at Toby, and he's shaking his head. I said, "Where's Leo?" Toby said, "He's over there by the bar."
We're in this big penthouse suite, and I look over, and there's Leo sitting on the other side of the room, and he looks all forlorn. I thought, "Oh sh*t."
And so I walked over to him, and he shook my hand. He said, "I'm so sorry. As soon as you walked downstairs, I got the big hand, I got pocket aces", and he didn't even have to finish; I knew what he was going to tell me. He was going to tell me that Bob Safai cracked his aces, because Bob had cracked my aces more times for six-figure pots than I cared to count.
DiCaprio: Top acting skills put to good use
So he proceeds to tell me that he picked up pocket aces, flops a set, and shoves all-in. Bob snap calls him with a four-high flush draw and hits it on the river, which sounded about right.
And so at first I just walked out, walked back downstairs to the bar, got a drink, and I started getting texts from Toby saying, "Hey, suck it up. If you want to win your money back, you got to come back up, or you're going to lose your seat."
I walked back up. I still wasn't ready to sit down. I walked out on the balcony, and Leo walks out. He said, "Hey, Houston, if it makes you feel any better, I'll kick in ten grand to the loss."
And I looked at him, and I said, "That's okay, Leo, don't worry about it."
I walked in. I said, "Molly, give me another 100 grand". And as I sit down, Bob Safai pushes the $200,000 in chips over to me. Everyone bursts out laughing, and I had just had a practical joke pulled on me by the best actor of our generation.
It just goes to show you that for a guy who can spot all the hustles, anybody can get taken. At least in this case, the outcome was favorable.
Feature image courtesy of Wiki Commons
