Billie Jean King
Bobby Riggs' pro tennis career peaked in 1939 when he lost in the finals of the French Open, then won Wimbledon (where he won the men's singles, men's doubles and mixed doubles titles), before going on to take the men's title at the US Open, thus earning himself the top spot in the world amateur rankings. Over the course of his career he would win 103 titles, compile a career record of 838-326 (71.9%), and five years after his retirement in 1962, be inducted into the International Tennis Hall of Fame.
In addition to being a world class tennis player, Riggs was also a world class gambler and hustler. He claimed in his autobiography to have won more than $100,000 by betting on himself to take all three Wimbledon titles in 1939.
In 1973, Riggs, by then 55 years old, saw a chance to gamble on himself once again, this time declaring that women tennis players were clearly inferior and challenging Billie Jean King to a three-set match. King knew better than to stoop and so demurred, at which point Riggs turned his attentions to Margaret Court, who at the time was the top-ranked women's tennis player in the world and was on her way to winning more Grand Slam titles than anyone ever (and had not yet outed herself as an unreconstructed homophobe).
Riggs and Court met May 13, Mother's Day, in Ramona, California, with Riggs winning 6–2, 6–1 in less than an hour in a match that would be predictably dubbed "The Mother's Day Massacre."
“In treating Riggs with contempt and not affording him the respect I would any opponent, I blundered," Court confessed In her 2016 autobiography.
Riggs wasted no time in re-issuing his challenge to King.
“I’ll play her on clay, grass, wood, cement, marble or roller skates,” Riggs said. “We got to keep this sex thing going. I’m a woman specialist now.”
Suddenly, King felt the need to defend the honor of women everywhere by facing down this decrepit gasbag.
"I thought it would set us back 50 years if I didn't win that match," King said years later. "It would ruin the women's Tour and affect all women's self-esteem."
Where Court took Riggs' too lightly, King trained as though she were playing Jesus himself. Because this was to be the first best-of-five match of her career, she worked hard on her stamina, and because the match was to be played at night, she steadily started shifting her sleeping patterns. She left nothing to chance.
On September 20, 1973, Riggs and King met in front of 30,000 fans at the Houston Astrodome, in "The Battle of the Sexes," a match that was broadcast live to an audience of 90 million worldwide with Howard Cosell calling the action. At stake was not just the dignity of women athletes everywhere, but a winner-take-all purse of $100,000.
Before play started, King was carried in Cleopatra-style on a gold litter borne by beefy dudes done up as Egyptian slaves, while Riggs rode a rickshaw pulled by four models, known collectively as “Bobby’s bosom buddies." In one of history's more regrettable sponsorships deals, “Bobby’s bosom buddies" all wore matching Sugar Daddy t-shirts, and Riggs presented King with a gigantic Sugar Daddy (that'd be a chewy caramel candy on a stick, for youngsters out there), while King gave Riggs a (male chauvinist) pig wearing a bowtie.
King wiped the floor with Riggs, taking him 6-4, 6-3, 6-3.