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Shortcut to Gambling Nirvana

Enlighten your path to enlarged winnings at poker, sports, blackjack and golf
Michael Kaplan
From the Print Edition:
Jay-Z, May/June 2009

(continued from page 2)


Dewey Tomko is well known in elite poker circles. He's taken home three World Series of Poker bracelets and has snagged nearly $5 million in poker tournament winnings. But his surefire moneymaker is playing golf. Tomko has raked in the dough by looking amateurish on the course. This is not done for show. He actually lacks a powerful swing and doesn't have much of a long game. Spot him on the driving range, and he appears to be the kind of guy you'd love to bet against.

Maybe we see some of ourselves in him. A lot of us view our tee shots as being a bit raggedy and practically camp out on the range, hitting drives till our arms are sore, wanting nothing more than to look majestic and crush the ball. Not Tomko. He spends most of his warm-up time on the practice green. And he offers what sounds like the most obvious golf advice imaginable: "Getting the ball in the hole is what it's about."

What he means is that winning money at golf requires a short game that exceeds your long game. Then you win those Nassaus by turning every match into a short game. For instance, when going up against a long-ball hitter, Tomko always suggests that they play from as far back as possible. "That way," he says, "we're both going to have a hard time getting up onto the green." His counterintuitive point being that once he gets near the green, his game is going to be a lot stronger than his opponent's. If he can turn a match into a chipping contest, all the better.

Another critical point to winning money at golf is simply being honest with yourself as to how good—or not—you really are. Maybe because golf is such a tough game, maybe because it really comes down to being a contest against our previous scores, we tend to exaggerate our abilities. Not a big deal if you're playing for fun with a few pals; critical when you're playing for money and negotiating for strokes.

Because casual golfers tend to inflate their skills, just by having a true grip on your bona fide handicap, you are already playing at an advantage when it comes to matching up. And, advises Tomko, if you think you have a lower choke factor than your opponents, be sure to suggest betting with an invisible doubling cube. Basically, when any shot is in the air, anybody can shout out, Double! Then, before the ball lands, whoever hit it must agree to double the bet or concede it and pay off at the pre-double rate. This can turn a low-stakes round of golf into something much more expensive, and it's a bonanza for those who can maintain composure.

But as Tomko reiterates, success at golf wagering all goes back to your short game. As he explains it, "Look at Doyle Brunson: he's 75 and can barely walk, but he beats guys like Phil Ivey and Daniel Negreanu by playing to the safe part of the green, executing a good short game and letting the other guys beat themselves. They get to 100 yards from the green, laying 1, and they should par. Instead they bogey the hole." Tomko laughs softly and adds, "I guarantee you, right now, Daniel and Phil are out on the driving range, hitting ball after ball. That's fun. Having a good short game is not fun. It's work. I don't know how many thousands of hours I've spent on improving my short game. But if you want to win money playing golf, that's the way you do it."

Michael Kaplan is a Cigar Aficionado contributing editor.

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