Bobby Riggs

Bobby Riggs was a tennis player best known for his provocative antics and, of course, the "Battle of the Sexes" match against Billie Jean King. Prior to his theatrical gender showdown, Riggs was a legitimate champion, winning Wimbledon and multiple US Open titles, though those were in the days when tennis players wore long pants and worried more about their backhand than their brand.

Riggs cultivated an image as a chauvinistic showman, a persona that served him well in the lead-up to his high-profile exhibition matches. He was less interested in advancing the cause of gender equality and more concerned with keeping the spotlight firmly on himself, preferably with a nice wager on the side.

His most famous moment, losing to Billie Jean King, solidified his place in sports history, albeit as the villain (or perhaps, the delightfully cartoonish foil). While it was a loss for him, it was a massive win for women's sports and a cultural touchstone that still resonates, proving that sometimes the best way to make history is to dramatically fail at stopping it.

Riggs's approach to life seemed to be one grand hustle, always looking for an angle, a bet, or a spectacle. His legacy is less about his undeniable tennis talent and more about his knack for self-promotion and his role in a match that transcended sport, even if he played it for laughs.