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With another US Open tennis tournament in Flushing Meadows, New York, underway, it’s interesting to recall that the state’s most famous showman (now relocated to Washington DC) once dreamed of a wholly-different spectacle.


Donald Trump has made more than a few headlines with dust ups involving women (see Rosie O’Donnell, Megyn Kelly, and Heidi Klum), but fifteen years ago he tried to orchestra a a battle of the sexes on the tennis court. According to John McEnroe, the real estate mogul attempted to set up a match between him and Serena Williams, but didn’t offer enough money to make it happen.

Donald Trump presents Battle of the Sexes Part Deuce: Serena Williams vs John McEnroe

Appearing in 2015 on Jimmy Kimmel Live!, McEnroe also offered that he thinks he could still beat Williams if the opportunity availed itself — with the caveat that his daughters — who were standing offstage — would likely disagree.

''My daughters are over there. I think it's mixed. They think I'd probably lose to Serena. I believe I could still take her.''

— John McEnroe, on his chances vs Serena Williams

As for Williams, she will be trying for a record-tying 24th Grand Slam singles title in the French Open and Wimbledon before the 2019 US Open rolls around.


Trump’s try at matchmaking was probably inspired by 1973’s heavily publicized “Battle of the Sexes” between Bobby Riggs vs. Billie Jean King.

Prior to his highly-suspect shellacking by King, Riggs appeared on 60 Minutes where his constant angling and hustle were on full display.