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."
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.
Leon beat the star 31 days in a row, for well over $3 million.
How, any reasonable person might wonder, did Leon get the star to continue playing after the star had lost even three or four times in a row? "Well, I didn't have to get him to do anything. He wanted to play. Twenty-five out of thirty-one of those times this guy had the advantage going into the fifteenth hole. I mean, he had me beat. All he had to do was shoot triple-bogeys coming in and he'd get the money."
Incredibly, as Leon and his caddie tried mightily not to laugh out loud, the star would consistently shoot 10s, 13s, even 18s when the pressure became intense.
"He kept playing because he knew he should have been winning. On paper he had way the best of it," Leon says. "But this is the key to gambling at golf: the winner is immune to pressure. He can always play to his ability. The loser can't."
Leon smiles faintly. "I've always been able to."
The world's greatest golf hustler does not attempt to disguise his talent--anyone who watches him swing a golf club immediately recognizes the man can play. His success, he says, is not the product of looking bad on the practice range and beautiful on the golf course; it's not the product of making intentionally unorthodox swings that look as though they've been constructed in a tool shed (a la Lee Trevino), and then shooting the lights out. He's the best in the business because when he gets nervous his game does not deteriorate. It gets better.
"I play a match for chicken feed and I don't do so well," Leon admits. "But when we're playing for something substantial it makes me more focused, more intense. In a big match I probably play better than my abilities."
Leon has played thousands of matches for tens of millions of dollars. But perhaps no single game was ever bigger than one he had with the CEO of a Texas-based oil company. "I met this fellow, we'll call him The Chairman, in Las Vegas, at the old Dunes golf course," Leon remembers. "This man was successful at everything he did. His entire life was one victory after another. The man had no fear. There was virtually no amount of money we wouldn't play for. Which was fine, 'cause that's basically been my policy my entire career."
In Las Vegas, The Chairman played the hustler in a "friendly" match for $50,000. Leon lost. "Not intentionally, mind you," he says, half-seriously. "I was giving him a few too many strokes. But the gentleman played great. And, naturally, I took every opportunity to remind him of that fact."
Flush with victory, The Chairman invited Leon to play in Austin, Texas, at The Chairman's home course. "We'll play for whatever you want," The Chairman told Leon. "Even up."
The Chairman was about a 4-handicap. The Hustler was scratch. "I liked my chances," Leon says, strolling to the 18th tee box.
The first nine they played, Leon beat the oilman out of $120,000. The next nine, The Chairman pressed his bets and lost $240,000. To Leon's delight, his opponent suggested they play again the next morning, double or nothing. "Funny thing about that match, I hadn't really played all that well the first day. Shot like a seventy-three," Leon recalls. "So even though I was playing for a quarter-million the next day, I wasn't too concerned. I knew I could only play better."
He did, posting a 69 on a course he had seen only twice before. The Chairman wrote Leon a check for $480,000. "That was about my best day on the golf course," Leon says, striping his drive down the middle of the fairway. "Made about thirty-five hundred per shot."
Leon's record against what he calls "very good players" is stellar. Against the players we watch on television every weekend, he claims he's "hardly ever lost." Indeed, professional golfers, Leon reveals, are usually his favorite opponents. "I'm much more fearful of a seasoned gambler than a touring pro," Leon says, lining up an 8-iron approach shot. "There's a huge difference, I mean a world of difference, playing for some sponsor's prize money and playing for money that you have to reach into your own back pocket for." Most professionals, whose skill level is admittedly far greater than even the best amateurs, will tend to wilt under what Leon calls "real heat."
"Without exception, the pros underestimate me and overestimate themselves. And when there comes a point in the match where they realize they might just have to pay off a real big number, well, they change. Gambling to them is a hundred-dollar Nassau. A really big match, a huge match, would be something like 5,000. For me, I don't even really start paying attention until 50,000 or so."
Among the name-brand professionals whom Leon admires, the ones he believes can play for their own money are Raymond Floyd and Lee Trevino. "So can Jim Colbert," he says, lacing his iron to within 10 feet of the pin. "But most of them...." He shrugs dismissively.
"I'll tell you a story," he says.
Several years ago, Leon played a very talented gentleman in a two-day golf match. So talented was this nice gentleman that he agreed to give Leon two strokes per side. The nice gentleman ended up owing Leon $18,000. He paid the hustler promptly half in cash, half in check. Leon never cashed the check. Instead, he framed it.
Leon likes telling this story not because of the money involved. It's one of his favorites because the nice gentleman he beat is one of the few men walking the planet to have won both the U.S. Open and the Masters. "Every time I see this guy on television," Leon says, "I think to myself what a nice gentleman he is."
Lately Leon has been devoting more time to a portfolio of business interests than to the golf course. The Senior Tour, he says, would be a challenge, a "great chase," but, in addition to the constant travel, there's not enough money in it to keep him interested. "But I plan to enter a few tournaments anyway," Leon says. "Just to compete and meet some nice people. That's all I want out of golf these days. Before, it was all about money. Now I realize anyone who plays and enjoys golf and enjoys the people he's with is a big winner, no matter what he does or doesn't accomplish."
Still, he says, he has one big golfing goal. In a couple of years he'd like to fulfill a lifelong dream and play in the U.S. Senior Amateur, which, should he win it, surely would be one of the most ironic titles ever bestowed.
"Yes, I suppose I fall somewhere between a professional and an amateur," he admits. "An amateur is, well, an amateur. And a professional is someone who plays for a living. I've been successful enough, fortunately, that I don't really have to do that anymore.
"But, on the other hand, if anyone's looking for a big game," he says, smiling, "I'm available."
Contributing editor Michael Konik is Cigar Aficionado's gambling columnist.