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ThePlayboy.comversation Antonio Esfandiari By Michael Kaplan

PLAYBOY: Your first trip to Vegas was in 2000, for the World Series of Poker. How'd you do?

ANTONIO ESFANDIARI: I went home busted. It was pretty depressing. I lost my entire bankroll of $7,000 and learned how not fun it is when you're broke. But I put together another $1,000 and played a crazy gambler friend of mine heads up for the whole amount. I ran it up to $4,000 and he wanted to go double or nothing. But I didn't want to do it because the $4,000 was meaningful to me. Then he said, 'Let's play for $10,000. If you win, I pay you within three months. If I win, you pay me within a year.' How could I say no? I busted him on the second hand, a day later he paid me $7,000 and we called it even. I had 11-grand and never looked back.

Playboy.com: Now you're doing a TV show with poker pro Phil "Unabomber" Laak. Tell me about it.

Esfandiari: It's called I Bet You, it's on the Mojo Network, and it's a lot of fun. We just walk around and make crazy bets on everything. We bet on who's a better panhandler, what color panties a particular girl is wearing, who has better sperm.

Playboy.com: Who does?

Esfandiari: I can't tell you because it hasn't aired yet. But I can tell you this: One of us has four times the average and the other one has 10 times.

Playboy.com: Does potency correlate at all with poker skill?

Esfandiari: I doubt it.

Playboy.com: During your early days of playing poker, did you ever think you could do it for a living?

Esfandiari: Honestly, I initially didn't want to. I viewed poker as a great way to make extra money. I wanted to have money when I grew up. I wanted a family. I didn't want to have to worry about money. And I didn't think poker would do that for me. Now, though, since the whole poker craze happened, and poker players have become celebrities, a brand new window has opened that I didn't know would exist. Nobody expected it.

Playboy.com: What is your favorite thing about being a professional poker player?

Esfandiari: I like not having a boss or set hours or a place to be at a certain time. I like the freedom. But I also like that there are no repeat situations. In poker every hand is unique. It's always new and you're always learning.

Playboy.com: Can you give me an example?

Esfandiari: There was a hand that I saw played at the Venetian recently. A player by the name of John Duffy raised, and a guy named Viff called before the flop. The flop came Ace, rag, rag. There were no draws at all. John checked, Viff bet, John raised. An Ace came on the turn and John checked. Viff moved all in and John insta-called. He had Queen high -- and it was good. One guy was calling to bluff and the other guy was betting to bluff. Neither one of them had a hand, and there must have been $60,000 in the pot. It was totally sick. I saw that and figured I better rethink my game.

Playboy.com: You've obviously achieved a certain amount of fame as a poker player. And it's a game that, as of late, has attracted a number of legitimately famous people from the worlds of film and music. Does your recognition-factor ever lead to your playing with celebrities?

Esfandiari: Oh, yeah. Just the other night I played with Nelly until the wee hours. He plays better poker than I would have suspected. Recently I played with Jessica Beal. She's a very nice person and is interested in learning the game.

Playboy.com: Who in Hollywood plays well?

Esfandiari: Tobey Maguire plays very well. Ben Affleck plays very good when he wants to. They're famous for what they do, but, at the poker table, they're regular guys who enjoy sitting around and shooting the shit. It's hard to enter the environment where you get an opportunity to play with these people. But if you're a known poker pro, you sometimes get a shot. From my perspective, I enjoy playing with anyone who has unlimited wealth and is not a professional.

Playboy.com: But you do it as a profession, and I'm assuming that you don't have unlimited wealth. In spite of that, though, you've played for stakes in which people routinely have six-figure swings. Do you ever sweat the money?

Esfandiari: I've never had trouble caring about money on the table. Once money is on the table, it's chips. It doesn't matter to me.