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The 18-hole Hustle

June 2024
17min read

During the golden age of golf, many of the sport’s greatest players never went pro. They couldn’t afford the pay cut.

It was a short putt, about three feet or so, and the stakes were only $5,000—pocket change for a guy like the poker champion John “Professor” Moss, even in 1939 dollars, not that Moss was prone to choking anyway. This was more about bragging rights, because his opponent that day was “Titanic” Thompson, the notorious gambler and proposition artist who, among other things, took $30,000 off the gangster Arnold Rothstein—the man who had bankrolled the fixing of the 1919 World Series—in a marathon poker game in 1928. Thompson had bet Moss he could not shoot 46 or better on a local nine-hole course in Lubbock, Texas, using only a four-iron.

Moss stroked the putt perfectly, dead solid straight at the center of the cup, but just as it reached the lip, it bent off to the side, as if repelled by some invisible force. Normally, Moss would have chalked this up to a fluke, like the ball hitting a pebble, but this was the second straight hole this had happened, so he knew something was up. He sent his man ahead to the next hole, and sure enough, some conniver had raised the cup just enough off the green to deflect the ball. Thus informed, Moss glared at Thompson, who broke into a wide, boyish grin. After some discussion, Thompson confessed to having raised the cups. Even so, Moss magnanimously agreed to finish the round, provided Thompson had the cups stomped back down into place. Moss shot 41 and won the bet.

In the days before television and corporate sponsors; in the days before the players became superstars, surrounded by personal entourages and traveling by private jet; in the days before golf became staid and safe, there was a time when the game had a more ragged edge. It was a time when golf was more sport than profession, a time when the game’s heroes went by the names of Sam Snead, Byron Nelson, and Ben Hogan.

For now, all that remains are the stories. Traded in clubhouses, across card tables, or over post-match beers, the sums grow a little larger, the propositions a little more outrageous with each retelling. Over time the stories have taken on the weight of myth.

As long as there has been golf, there has been gambling. And where there is gambling, there is bound to be hustling. Call it human nature.

In the postwar days of the 1950s, golf underwent a tremendous surge in popularity. Course construction boomed, particularly in the South and West. In places like Miami and Las Vegas, the money seemed to grow on palm trees. Big-stakes matches were common, and at courses like La Gorce in Miami and the Dunes in Las Vegas, movie stars mixed with mobsters. The places became magnets for ringers, hustlers, and con men from around the country. This was the golden age of golf hustling.

As long as there’s been golf, there’s been gambling. And where there is gambling, there will be hustling.

Bobby Riggs, tennis champion, showman, huckster, and ebullient male chauvinist—the instigator behind the famous “battle of the sexes” match against Billie Jean King—was known as a hustler long before he took to the court inside the Houston Astrodome one sweltering September evening in 1973. A compulsive bettor, Riggs once claimed he never played a tennis match in which he didn’t have money riding on the outcome. While his betting antics became the stuff of tennis legend (he claimed to have won $108,000 on a parlay that he would sweep the men’s singles, men’s doubles, and mixed doubles championships during his one and only trip to Wimbledon in 1939), it was in golf, not tennis, that his reputation as a hustler came to full flower.

First taking up the game as a way to kill time between matches on the early pro tennis tours, Riggs discovered what golf was really all about after quitting tennis in 1952 and moving to Florida. When he saw ordinary golfers shooting 85s and 90s and betting all kinds of money, it was like discovering a rich uncle he never knew he had. “How long has this been going on?” he asked himself.

Tagging along with good players, Riggs watched carefully and learned. Through imitation and practice, he was breaking 100 consistently within a year. Not long after that, he was shooting in the 80s. He got his handicap down to 16 and started hanging around courses in Miami—La Gorce Country Club, the Seminole, and the Bayshore public course.

La Gorce, a posh club whose membership included more than 150 millionaires, was known as Hustlers’ Haven. “It was like an open-air poolroom,” Riggs said. “La Gorce was a den of thieves. All the ringers, hustlers and smart guys were there. If you didn’t know what was happening, you wouldn’t see an elephant if it jumped up on the table. But if you didn’t let yourself get outmatched, you won. You’ve got to get into the right match-ups, know your own levels, and the other guy’s.” Soon Riggs was keeping company with people who went by names such as the Stork, Shaggy Ralph, the Dog Man, Charlie the Blade, and Three-Iron Ward—men with deep tans and a nose for action. They traveled the circuit, stalking the clubhouses and driving ranges. Working in concert or alone, they sought easy marks: tourists, businessmen on vacation, and millionaires from Texas—suckers, or “palefaces,” in the parlance of the trade. They wore long-sleeved shirts, gloves on both hands, and big Panama hats. Among themselves they joked about being “too tan.”


Many of these hustlers were terrific golfers and might have played professionally, but they found the money from hustling easier and more plentiful. At the time a top pro might earn $30,000 a year, a sum a first-rate hustler could make in a week. Asked if he would ever turn pro, Titanic Thompson replied, “I could not afford the cut in pay.”

Born Alvin Clarence Thomas, Titanic Thompson once won $1,000 on a bet that he could drive a golf ball 500 yards. He did, teeing up on the edge of a frozen lake. (Decades later the poker champion Amarillo Slim won $38,000 on a variation of the bet, claiming he could hit a golf ball a mile. He found a bigger lake.)

A relative latecomer to golf, Thompson took up the game when he was nearly 30, in 1921. Already a crack shot, a champion bowler, a good pool player, and an expert at dice and cards, particularly poker, he learned quickly. In 1934 a group of Dallas businessmen put up $3,000 to host a match between Thompson and a young Byron Nelson. By then Thompson had become famous in the golfing community, and people came from hundreds of miles to witness the match. Nelson spotted Thompson 3 strokes, and lost, shooting 68 to Thompson’s 70. Tommy Bolt, the 1958 U.S. Open champion, once said of Thompson’s golfing ability: “He could have been the greatest.”

Trophies, however, never interested Thompson. His rewards needed to be financial ones, and he left nothing to chance. One of his favorite ploys was to play a rich oilman right-handed. After collecting his winnings, Thompson would offer to give his opponent a chance to win it all back, for double or nothing, by playing left-handed. Unknown to the mark, however, Thompson was a natural lefty. He also liked to take promising young golfers under his wing, teaming up with them to relieve the unsuspecting. Among those to apprentice under Thompson was the former touring pro Lee Elder. In 1965 Thompson bankrolled Ray Floyd in a money match against an unknown kid out of Dallas named Lee Trevino. Trevino won, putting Thompson out $9,000.

Hustlers, like all craftsmen, were individualists, each developing a routine or gimmick. Charlie the Blade used only one club, a four-iron, but could do as much with it as most scratch golfers could with all 14 clubs. The Stork played every shot standing on his right foot with his left stuck up behind him. The Whiskey Drinker would swig from a flask he carried in his golf bag, growing more congenial and unsteady on his feet with every swing. By the time he reached the ninth hole, he tipsily demanded that all bets be doubled, after which his demeanor and game miraculously straightened out. Few suspected that the amber liquid in the bottle was tea.

Riggs was always calm about the “big bet,” he said: “Pressure makes me produce. Kills most guys.”

Like all craftsmen, hustlers had their own hierarchy. The top tier viewed men like the Whiskey Drinker with disdain, considering them nothing more than cheap tricksters. The best were artists, men who turned the common hustle into an elegantly constructed con. La Verne Moore, alias John Montague, first appeared around 1930. A crack golfer and master of trick shots, he once challenged a sucker by boasting that he could pick off a sparrow sitting on a telephone wire with a ball hit by a mid-iron. He did. Another time he bet that he could blast a completely buried ball out of a sand trap and onto the green with a wedge. He did that too. He’d crack the window in his motel room six inches and chip balls through the opening over and over without breaking the glass. Legend has it he challenged Bing Crosby for high stakes and took him for a wad of cash, playing with nothing more than a rake, a hoe, and a baseball bat, while Crosby was allowed to use all his clubs.

From such tutors, Riggs said, “I learned all the angles, I mean all the angles.” Earning what was called a “traveling handicap,” Riggs legitimately acquired his handicap from the back tees at a very difficult course, but played his money matches from the middle tees, giving him the “fair advantage” he deemed necessary.

While everybody would be leery of taking on the Wimbledon champion in tennis, nobody was afraid to bet on golf against the funny little man with the squeaky voice and jaunty walk. Though an average golfer compared with the other sharpies, Riggs was a superior competitor, becoming positively inspired when playing for high stakes.

“I always rise to the occasion for that big bet,” Riggs said. “Pressure makes me produce. Kills most guys. Mortifies ’em. I love a contest, a game, a challenge. To be a winner, you’ve got to be an appraiser. You’ve got to be able to play at your best under pressure. And more money creates more pressure. Money is the finest fuel in the world. You see, if you’re betting all the time, everything is just another bet. You don’t even think about the money after you’ve made the arrangements. You’re used to it. And you’re usually playing with people who have more money than you do. Now that’s an advantage, because they’re thinking about the money and they play six strokes worse than they usually do. I play better under pressure.”

Riggs called himself the best money player of all time. His biggest coup came in 1953. The match was played over the course of a week at the Greenbrier Country Club in White Sulphur Springs, West Virginia, then Sam Snead’s home course. The participants included Riggs; Dan Topping, owner of the New York Yankees; Jose Dorelis, called “the Count” because he wore a monocle; and Ray Ryan, an eccentric oil tycoon and real estate developer from Evansville, Indiana, who was reputed to have mob connections. Ryan was a mediocre golfer who loved to bet high.

Riggs was at the Greenbrier after a Calcutta pool (see sidebar on page 64). He had not played well and decided to stay over at the hotel to practice when Ryan showed up.


Riggs gave him a stroke a hole, two on the par fives, and sometimes two on the par fours. “I started out playing for what I could afford to lose,” Riggs said. “Now Ryan, he thought he could win. He thought he had a license to steal, a real bargain, but that week he went completely crazy and shot above his game.” Ryan’s usual 100 blew up to around 135.

“He was hitting the ball sideways he was so bad,” Riggs recalled. “He was pressing bets with both hands, and by the time he got to the eighteenth tee the first day he was deep in the hole. I’ll never forget. He pressed again on that hole and by three-putting he lost $100,000 right there. Boy, they were big times. At the end of that week he owed something like $500,000. Now, you bleed a lot of rich guys and you oughta hear ’em squawk, like they’d been stabbed for chrissakes. But not Ryan. The next day he asked us boys to stop by his suite. We arrived and he was sitting behind a card table with a suitcase full of thousand-dollar bills. We lined up and he paid us off without flinching. With a smile. He was a great high roller. None better. All he said was: ‘Boys, If I win tomorrow, I want to get paid in the same way.’” In a postscript to the story, Riggs said he lost all the $180,000 he claimed to have won in a gin game against Ryan the next week in New York.

But the stakes did not necessarily have to be high. Sam Snead recalled a day when Dutch Harrison, a former top golfer who had a reputation as a bit of a hustler, lost a $5 bet to a player he thought was an easy mark.

“Dutch, this is really an honor,” said the man. “I’m going to frame this bill.”

Harrison grabbed it back and said, “In that case, I’ll write you a check.”

When they did happen, the big-money matches could become spectacles. With as much as $100,000 a round at stake, crowds gathered to watch the action, and as the players made their way from hole to hole, caravans of golf carts trailed them: club members, golf fans, fellow hustlers, and the merely curious. The noise, the crowds, and the commotion drew the ire of many other club members.

In addition to making bets with the other players, the players would often have a halfdozen other wagers going with bookmakers who followed the group around the course. “These guys would try to distract me when I was about to make a shot,” Riggs recalled. “Just as I leaned over the ball, they’d crash two golf carts together. They’d move around me on the tee or the green to disturb me. But I knew what they were up to and I never let them bother me.”

Among Riggs’s regular partners was Martin Stanovich, better known as the Fat Man. Weighing in at 230 pounds, Stanovich owned one of the most preposterous swings in golf. Feet planted apart, head hung low, he had a ridiculously short backswing, and lunged at the ball like a man trying to kill a cockroach with a crowbar. But he almost always hit the ball a little farther and a little more accurately than anyone else.

A legend in golfing circles, Stanovich belonged to at least a half-dozen country clubs around the nation. Playing year-round, he spent four months in Florida, four months in Pittsburgh, four months in Chicago, and four months in San Francisco. Given stakes as high as $100,000 a round, he once estimated he earned $11 million from golf but figured he gave back $6 million to the ponies.

“I’ve played Riggs and beat him four times,” Stanovich once told a reporter. “Trouble is, he won’t play for real money unless I give him half the golf course.”

Stanovich was an equal opportunity gamesman, taking on pros, hustlers, and “nice people who just love to lose money.” But being an amateur, he demanded three strokes from any pro as a matter of policy. “Then I don’t have to work so hard,” he said. A scratch golfer, against everyday opponents the Fat Man allowed a 12-stroke handicap but wound up taking their money anyway, clucking sympathetically and offering tips to improve their game during the round.

Stanovich made a lot of friends and gained a lot of admiration from players on the tour, among them Lee Trevino, Ken Venturi, and Al Besselink. Venturi recalled Stanovich’s bank-rolling him in money matches in San Francisco before he joined the pro tour. “He was a great competitor. I mean, the bets were so huge,” said Venturi, who would earn a cut of the winnings from Stanovich. “I mean, [Stanovich] could have really put the monkey on my shoulder if he told me how much people had bet on me,” Venturi said. “But he never said a word and, to tell the truth, I didn’t want to know.”

“He had aspects of a being a hustler,” said Besselink of Stanovich, another player who made the rounds in Miami before joining the tour. Stanovich, Besselink said, “made games. He couldn’t shoot 65 or 66, but he’d bet $10,000 and could shoot 69 or 70 every time. He knew how to play for money.”

At the time, prize money in professional tournaments rarely exceeded $5,000, and for all but the top players the label “golf bum” was very real, as many on the circuit were forced either to mooch off one another or rely on the generosity of patrons for places to stay. The golf legend Ken Venturi remembers baby-sitting for his friend and rival Gene Littler while on the road. Many tournament players supplemented their income by hustling on the side. They would arrange money matches in pro-am tourneys that preceded the main event or get bankrolled in games set up by bookies or hustlers like Stanovich.

With $100,000 a round at stake, crowds would gather, and caravans of golf carts trailed the golfers.

Money matches not only helped keep pro players solvent, Venturi says, but also helped them hone their competitive edge. After all, it’s one thing to be putting for a million dollars of someone else’s money, but it’s quite another to be putting with $1,000 of your own on the line. Or, as Trevino is quoted as saying, “Real pressure in golf is playing for $10 when you’ve only got $5 in your pocket.”

If Besselink fell out of contention in a tour event, he might intentionally play badly on Saturday to be among the highest scorers, thus earning him an early start on Sunday. He then started placing bets with bookies who followed the tour. “There would be no wind, no pressure of trying to win, and smooth greens with no spike marks. I’d bet my score against the 10 leaders. I’d shoot 68 and beat nine of ’em and make more money than the winner.”

Besselink says he earned a total of $187,000 in prize money over the course of his more than 10-year career on the tour, but he figures he spent millions gambling in big-money matches—“and I never had to hold a gun to anybody.”

Besselink, now 83, was a golf Wunderkind who never graduated from high school but was recruited by the University of Miami in 1942 to captain its fledgling golf team. Playing in the Southern Intercollegiate Athletic Conference finals, he bet $500, all the team’s expense money for the trip, on himself to win. He did, in extra holes. Before joining the pro tour, he earned a living playing money matches.

Back then, he says, he lived “to gamble and to bet, on anything, absolutely anything.” Living in Miami, the tall, blond, blue-eyed, and fair-skinned Besselink was known as “the Viking.” “We used to go over to Normandy Shores Golf Club on Miami Beach and sit around all morning trying to make a game. There’d be all kinds of games, $50 games, $100 games, $500 games, $1,000 games, you name it. You sit around long enough, you’d find what you’d want.”

Was he a golf hustler?

Hustler ’s the wrong word,” Besselink growls. “I never had to cheat anybody. My best game was playing hustlers, playing the guys who cheated and tried to take advantage of everybody. I wanted to play either them or multimillionaires. I never tried to beat anybody who didn’t have any money.”

Of course, the essence of the hustle is to make the victim think he’s getting an even break. In Riggs’s case, this meant selling people a situation they really didn’t want but, 9 out of 10 times, ended up buying anyway, only to realize later that they had been had. His advantage in golf was that nobody knew how good he really was. He bragged that by offering long odds or a big handicap, by appealing to “the larceny in everyone’s soul,” he could get a $10 bettor to bet $100, thus immediately putting him under pressure.

Golf matches, someone once said, are not won on the fairways or greens. They are won on the tee, the first tee. “People misunderstand the mentality of a hustler,” Riggs explained. “It doesn’t matter how well you do things, it’s how you negotiate the handicaps.”

Jeanne Carmen was born in Arkansas in 1930 into a family of poor cotton sharecroppers. She ran away at 13, first to St. Louis, then to New York City, where she eventually landed a job as a fashion model. In 1949 she got an assignment to model clothing for Jack Redmond, a local golf pro and shop owner. Carmen, who had never seen a golf course, was modeling different outfits at Redmond’s indoor golf range when he playfully asked her to take a swing at the ball. A lefty, she spun the right-handed club around in her hand and, with the back side of the club face, smacked the ball into the canvas backdrop, knocking it off its support.


“You sure you haven’t played before?” asked Redmond. He then set up the backdrop again. “He had me stand on the other side of the ball and hit right-handed,” Carmen recalls, “which was harder, but I knocked the drape down again.”

Redmond asked her to come in the next day: “I’d like someone to see you.”

The next day Redmond had the golf champion Jimmy Demaret watch as Carmen hit balls.

“They were oohing and aahing,” she says, “and I thought, ‘What’s the big deal?’ I don’t think this is a very difficult thing.”

Finally, Redmond said, “I think I can make a trick-shot artist out of you,” and asked if she would mind coming in two or three times a week.

“Sure,” she said. She hit nearly every day, sometimes for hours on end, for six months. Then she was ready.

“I could stack three balls on top of each other, which itself is very hard to do. I’d hit the middle ball 200 yards, the top ball would pop up and I’d catch it, and the bottom ball would rest, untouched. I could hit the ball 200 yards while standing on a chair on one leg. I could hit a flagpole 150 yards out.”

She and Redmond traveled up and down the East Coast, putting on three shows daily at various clubs and earning upward of $1,000 per day. For their finale, she would have a volunteer from the gallery lie flat on his back and tee a golf ball between his lips; then she would drive it 200 yards without disturbing so much as a whisker.

Within a year personal differences ended this lucrative partnership. Carmen then met a dapper young man from Chicago, John Roselli, and moved with him to Las Vegas. Roselli was a lackey in the Chicago mob who helped run the Sands Hotel. When he found out about Carmen’s golfing talents, he told her, “Look, honey, we’re going to play a little game here.” The way he described it, she says, “He said we’re never going to take a nice guy. We’re only going to take the assholes, and I know who they all are.”

“I could hit the ball 200 yards while standing on a chair on one leg. I could hit a flag- pole 150 yards out….”

“Well, that sounds good to me,” Carmen recalls saying. “What did I know?”

Roselli would plant her in a lounge reading a magazine. He’d sit at the bar, scouting for pigeons. Eventually he’d strike up a conversation and steer it toward golf and gambling.

“That’s not so great,” Roselli might say. “Even I could beat that.” Then, pointing at Carmen, “Hell, even she could beat that.”

Says Carmen: “And the guy might say something like ‘Maybe in the bedroom but not on the golf course.’”

Wanna bet?

The group then would go over to Carmen, who, pretending to be a stranger, would innocently agree to be a pawn to their betting proposition. Dressed as provocatively as the era would permit, she would stand on the first tee and spin the club around in her hand, feigning to have never played before.

“I’d hold the club all wrong and then duff it, or slice it, whatever. After a couple of holes the guy would say, ‘This is getting to be a bore. I’m going to win this hands down.’ And John would say something like, ‘Give the lady a chance. Give it a few more holes.’ And then I’d get a little better and a little better. Until right at the end, when I’d start reeling them in. We’d win every time. They never knew what hit them.”

The two worked the scam for about a year, until one day when Carmen slipped. She’d had a drink while waiting for Roselli to set up the mark, and, a bit tipsy, started playing too well too soon. The man knew he had been set up. “He was carrying on, complaining,” Carmen says, “and Johnny said, ‘Look, pay up, you lost the bet. Pay up and let’s call it a day.’ But this guy refused.”

Roselli told Carmen to go to her room; he’d call her later.

“He then roughs this guy up. He calls me and tells me to get to the roof of the Sands Hotel. I get up there and open the door to see Johnny toss this guy over the side. Oh, my God. I’m in shock. I’m crying. So Johnny says, ‘Come over here and look.’ I didn’t notice that the guy had a rope tied around his ankle. I go over and see this guy dangling down there… . He pulls the guy up and … Johnny’s got his money and cuts the guy loose.

“Right then I decide I’m in too deep. I had to get out of there. I go pack my things.” She moved to Los Angeles and became a star in B-movie potboilers such as Guns Don’t Argue , Reckless Youth , and Born Reckless .

For Riggs, the bigger the foe, the sweeter the victory. “Listen. I love millionaires,” he said. “I really do. Give me a millionaire every time. There were a lot of them around then. Beautiful, the salt of the earth. Wherever I went, they were lining up waiting for me. They loved playing with me. They loved playing with me. It was a challenge. They liked being taken by the best.”

Eventually Riggs left Florida for New York, where his wife got him a job at the family company. He settled down, more or less. By the time of his match against Billie Jean King in 1973, the golf-hustling scene he had left behind had largely faded. Scandals convinced many clubs to clamp down (by the time he left Miami, Riggs had been banned from most private clubs and forced to ply his talents on public courses). This, and the injection of big money into the professional game, meant that career hustlers had not only fewer places to play but more incentive to earn their money legitimately.

Today word occasionally filters out of a big-money match. The basketball superstar Michael Jordan once admitted to writing a $57,000 check to pay off a golf gambling debt, and the poker champion Doyle Brunson not long ago got involved in a game with an $80,000 Nassau (see sidebar). After all, gambling in golf will be a constant. But the days of the big-time hustlers are gone. “I’m sure there’s someone out there doing it,” says Ivan Smith, a former touring pro. “But the whole scene is long past. Ninety-five percent of the high-stakes gambling going on in this country is strictly millionaire to millionaire.”

The fact is most good golfers can now earn a living playing professionally. “The hustlers were bigger back then because there was more money in hustling than playing pro golf,” Smith says. Today a player on one of the satellite tours can earn more than most players on the main tour did 30 years ago. Golf, says Smith, has lost its edge. The game has become safe and predictable. It is, Smith says, all “briefcases and cell phones.”

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