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The Hustler

One of Golf's Biggest Money-Winners Has Never Appeared on the Pro Circuit
Michael Konik
From the Print Edition:
Danny DeVito, Winter 96

(continued from page 1)

Eventually, Leon decided to treat his gambling not as an addiction, but as a business. "That's what's made all the difference. Gambling stopped being fun and it started being a way to make a living. I figured I wasn't going to get involved in nothing unless I was getting the best of it. If I didn't have the advantage, I wouldn't play. That's the secret. Find something where you're getting the best of the deal and stick with it till there ain't no money left to win."

Nowhere did Leon have the best of it more dramatically than on the golf course. He was not, by his own admission, much of a player in his early days. Like anyone who takes up the world's most frustrating game, Leon initially struggled with golf, losing thousands of dollars in bad bets in the process. "Hell, I couldn't break 90 and I'm playing guys for $5,000! But I knew one day I'd come back and beat those same guys for 10 times as much. That's the great thing about golf," he says, peppering a flagstick 160 yards down the range. "Nobody can stop you from shooting a good score. You're competing against yourself and the golf course. I decided I was never going to let me beat me."

In one year, practicing 80 hours a week, Leon went from an 18-handicap to a 6. A year later he was down to a 3-handicap. And a year after that he was playing at scratch--a level of accomplishment he maintains today, nearly three decades later. Watching him play a "casual" (for a meager $3,000) 36 holes, one realizes that Leon has the kind of golf game that could easily dominate the Senior PGA Tour: he's monstrously long off the tee, surgically precise with his irons and possesses a short game worthy of Corey Pavin. The man is so good it's scary.

But, according to Leon, being able to shoot low scores is not the key to being the world's greatest golf hustler.

"You want to win money on the golf course," he says, lining up a short birdie putt, "you got to get your opponent out of their element and you into your element. Sure, you got to have some ability, but it's more important how you react under pressure. Playing for 50 bucks, guy might shoot the grass off the course. But playing for 200, and that same guy might not be able to break a 110. On the other hand," he says, calmly sinking his putt, "some guys get better the higher the stakes."

He smiles. "I'll tell you a story."

Several years ago, Leon heard from a friend in the entertainment business that a certain television action star--one of the biggest celebrities of the late '80s--was looking to play some big-money golf matches. The television star wasn't a particularly good player--he had broken 90 only a few times in his life--but, given enough strokes, he would play for "a whole bunch of money." With no guarantees of a match, only the faint promise that the star would consider any "reasonable offer," Leon flew to Hawaii, where the star kept one of his many vacation homes, on Maui. After checking into a hotel, Leon went straight to the golf course to evaluate his prey.

"The guy wasn't as bad as some people had told me he was. But he also wasn't as good as he thought he was," Leon recalls. "I figured I'd take a shot. If he beat me once I was going to quit him. But I felt somehow that wasn't going to happen. No, sir, I was going to make sure of that."

The art of Leon's business is not, he claims, being able to hit 300-yard drives and hole every bunker shot. "Sure, you got to be able to play some," he says. "But what I do is all about negotiating and evaluating. I've always been pretty good at matching up. Learning how to make a good match is 90 percent of the game."

Leon offered the star what seemed to be a generous offer: 18 shots in match play and 22 shots in medal, or stroke, play. The medal play bet was for $25,000. The match play bet was a $50,000 Nassau, in which the players compete for three separate prizes: the front nine, the back nine and the overall.


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