

A tennis hustler who turned a carnival-style challenge match into a defining cultural moment for women's sports.
Bobby Riggs was a champion who never quite fit the country-club mold of tennis. He won Wimbledon in 1939, sweeping the singles, doubles, and mixed doubles titles, but his true legacy was forged decades later. After a successful pro career, he re-emerged in the 1970s as a self-proclaimed 'male chauvinist pig,' challenging the top women players to prove men's superiority. His 1973 'Battle of the Sexes' match against Billie Jean King became a national spectacle, watched by millions. Riggs's theatrical antics and King's decisive victory transformed the event from a stunt into a powerful symbol for the feminist movement and the legitimacy of women's athletics. He remained a complex figure, part showman and part skilled tactician, who accidentally helped change the game forever.
1901–1927
Grew up during the Depression, fought World War II, and built the postwar economic boom. Defined by shared sacrifice, institutional trust, and a belief that hard work and loyalty would be rewarded.
Bobby was born in 1918, placing them squarely in The Greatest Generation. The events that shaped this generation — world wars, depression, and rapid industrialization — shaped the world they entered and the choices available to them.
The biggest hits of 1918
The world at every milestone
World War I ends; Spanish flu pandemic kills millions
The Great Kanto earthquake devastates Tokyo
The Empire State Building opens as the world's tallest
Jesse Owens wins four golds at the Berlin Olympics
World War II begins; The Wizard of Oz premieres
Israel declares independence; Berlin Blockade begins
NASA founded
Martin Luther King Jr. and Robert Kennedy assassinated
First test-tube baby born
Pan Am Flight 103 bombed over Lockerbie
Oklahoma City bombing; Windows 95 released
He was a notorious gambler and hustler, often placing bets on himself in matches where he deliberately lost the first two sets.
Riggs served as a physical education instructor for the U.S. Navy during World War II.
He claimed to have won over $100,000 in a single day by betting on himself in various matches and side-bets during his 1939 Wimbledon run.
His famous match against Billie Jean King was played on September 20, 1973, at the Houston Astrodome before a record tennis crowd of over 30,000 spectators.
“The best way to insure a win is to bet on yourself.”