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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

He has probably won more money playing golf than anyone in the history of the sport. More than Jack Nicklaus, more than Tom Kite, even more than Greg Norman, the sport's all-time leading official money-winner with more than $10 million in tournament earnings.

Only you've never heard of him. He does not endorse golf balls or have his own line of sportswear. He's never won a major championship. Indeed, he's never even played in a professional golf tournament. If you were to see him hitting balls at your local practice range you would not recognize his face, nor would you be able to identify his peculiar golf swing as you would, say, that of Fred Couples or Nick Price.

He is a cipher, a man who prefers the shadows to the spotlight. He's anonymous. And he likes it that way. For that's about the only way a man in his line of work can run his business.

He is the world's greatest golf hustler.

With the understanding that this magazine would protect his true identity, this 48-year-old hustler--we'll call him Leon--has granted Cigar Aficionado his first interview in 30 years of hustling golf bets. [Editor's Note: Certain details in this article have been changed to protect the subject's anonymity.]

The game of golf has been surpassingly good to Leon. Thanks to his victories on the links, he has his own private jet, a sprawling 6,000-square-foot mansion in upstate New York and a fleet of luxury automobiles in his six-car garage; he even has his own golf learning center in the basement, fully outfitted with video cameras and swing-analyzing computers and all manners of techno-gadgetry. Thanks to his exploits on the golf course, Leon has all the trappings of wealth that typically accompany the wildly successful and the famous.

It wasn't always that way. "I grew up dirt poor," he says, stroking towering wedge shots on the practice range of a famous golf course in south Florida before we head out for a round. "We lived in a small town in Tennessee, about 1,400 people. No indoor toilet facilities, four kids to one bedroom--it was tough." The memory does not seem to pain him so much as amuse him. "Even as a little boy, seven or eight, I knew I was going to be something. Just didn't know it was going to be a gambler."

His voice is still thick and slow, like apricot nectar. He still has the courtly manners of a Southern gentleman. But Leon's coal-black eyes are not those of a country hick who has somehow wandered awe-struck into the big city. They're the eyes of a cold, calculating killer, the eyes of someone who refuses to lose at anything.

"I was introduced to gambling as a youngster," he recalls. "I grew up around pool tables and games of marbles, and from the start I enjoyed the competition. And I enjoyed coming away with more than I started with. Course I wasn't very good as a kid. Shoot, I'd bet on anything, just to gamble. As a 10-year-old I bet the grocer on the World Series, Yankees versus Dodgers, and I lost all my paper route money. Hell, I just loved the action."

As a teenager, Leon worked "here and there" at factory and foundry jobs, "but that wasn't for me. I was already making more money shooting pool than I could ever make punching the time clock. Almost from the start I was a successful gambler. Only problem was I couldn't hold onto my money, I couldn't manage it right. I'd win $80,000 playing nine-ball and turn right around and blow $100,000 on horses and sports. This went on for years."


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