Before Wimbledon in 1939, Riggs visited the London betting shops and was stunned to see he was listed at 25–1 odds to win the men’s singles championship. So he placed a remarkably presumptuous parlay bet on himself that would only pay off if he’d win the singles title, the doubles championship, and the mixed-doubles title. At Wimbledon, then an amateur tournament, no one had ever won all three in the same year. But at age 21, Riggs pulled off the remarkable feat and won, from the bookmakers, a total of $108,000, more than $1.7 million in today’s dollars. “I blew it all back on gambling like any young kid will do,” he told Tennis Week in 1995. “I liked to go to the casinos and bet on the horse races and play gin. I got overmatched a few times.”
But Riggs was rarely overmatched on the tennis court. Twice, he won the U.S. singles championships at Forest Hills, in 1939 and 1941. After serving in the Navy during World War II, Riggs won U.S. Pro singles titles in 1946, 1947, and 1949.
And always, Riggs had a bet on the outcome of his match. “I’ve got to have a bet going in order to play my best,” Riggs wrote in his 1973 memoir, Court Hustler. At least once, he had a bet going and played his worst. Tennis historian Bud Collins recalls a 1940s doubles match in which Riggs and his partner cruised to a two-set lead. But they then lost by dumping the next three sets, Collins says. The fix was obvious. “Well, there’s always money with Bobby,” Collins says. “The jingle of tennis was always there.”
After Riggs’s tennis career ended, he continued to play against seniors and amateurs at clubs in Chicago, New York, and, later, in California. He was in such supreme control of a match that players say he had the ability to drop a first set or even two sets, bet on himself at fatter odds, and then come storming back to win. “Staying in the barn” is what Riggs’s best friend, Lornie Kuhle, calls this hustle. “[It] means you’re not giving it your full effort, yet your opponent thinks you are,” Kuhle says. “He led you to believe you really had a chance to beat him. As soon as the bet was increased, he came out of the barn, and he beat you. Then everybody would scream bloody murder and foul. Bobby would stay in the barn a lot—on the golf course, on the tennis court.”
Before long, Riggs was playing more golf than tennis. That was because golf’s handicap system made it easier for Riggs to disguise his true talent; every golf gambler knows most wagers are won during the first-tee negotiations. “The second worst thing in the world is betting on a golf game and losing,” Riggs often said. “The worst is not betting at all.”
In the 1950s, Riggs was the resident tennis pro at the Roney Plaza Hotel, a Miami Beach artdeco magnet for celebrities and mobsters who enjoyed wagering. “Bobby was hanging around the unsavory people,” says Gardnar Mulloy, 99, a close friend of Riggs’s and a former U.S. number-one player. “I’d seen him with people that normally you would think you wouldn’t want to be with. And he was always betting big money—it was always, it seemed to me, a fix.” In those days, Riggs played golf for money with South Florida mobster Martin Stanovich, nicknamed “The Fat Man.”
Riggs also gambled on the links with Jackie “The Lackey” Cerone, a hit man for the Chicago Mafia and protégé of mob boss Sam Giancana, according to Riggs’s son and Kuhle. As he caddied for his father as a teenager in a money match against Cerone, Larry Riggs says he noticed that Cerone and his pals kept brazenly riding their carts over his father’s ball. They kicked the ball too, when they thought no one was looking.
Bobby Riggs just smiled. “These are rough guys,” he told his son. “These guys—you don’t mess with these guys. Just don’t ask any questions. Just keep your mouth shut.”
Larry Riggs was a child of Bobby Riggs’s first marriage, which ended in divorce. Riggs’s second marriage was to a woman whose family owned the American Photographic Cos. in New York, a $20 million a year corporation where Riggs worked during the 1960s. He wore a suit and necktie and took the commuter train from Long Island to Penn Station. He tried to satisfy himself by playing cards and golf on the weekends, but it wasn’t enough action. His second wife divorced him in 1972, handing Riggs a $1 million-plus divorce settlement.
With that stake, Riggs moved into his older brother’s duplex apartment in Newport Beach, California. Riggs wagered every day on things he could control, like tennis and golf. “Bobby had the guts of a burglar on a tennis court or on a golf course,” says tennis legend Tony Trabert, 82, a close friend. “He could goad people or needle people or set people up by purposefully losing a set or two and get the bet up to higher stakes and then win with ease. He just had amazing control.”