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While the US Open tennis tournament continues apace in Flushing Meadows, New York, the state’s most famous showman stole the headlines with a surprise trip south of the border for a meeting with Mexican President Peña Nieto. Years ago, Donald Trump was intent on creating a spectacle of a different sort.


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 different kind of battle of the sexes. 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 last October 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 is busy trying for a record 23rd Grand Slam singles title. She got off to a good start at the US Open on Tuesday with a 6-3 6-3 victory over Russian Ekaterina Makarova at the Arthur Ashe Stadium.


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 came on the Tonight Show with Johnny Carson to give the host some tennis pointers.