Let’s head back to the year 2000. It was a year wherein the Williams sisters dominated women’s tennis, John McEnroe said stupid, borderline-sexist things about them, the nation was rocked by political turmoil, and Donald Trump was somehow a thing. So, you know, practically a lifetime ago, almost unrecognizable to today’s world.

McEnroe’s comments back then, mentioning that both Venus and Serena would struggle to win against college or senior men’s players, kicked off a brief back-and-forth that played out through the media. Ever the opportunist, Donald Trump’s attention was caught, and Selena Roberts (later of A-Rod steroids fame) worked the story for The New York Times:

Donald Trump handed John McEnroe a letter on Friday that contained a proposal for McEnroe, the 41-year-old Hall of Fame player, to meet Venus or Serena Williams in a $1 million winner-take-all match at his Trump Taj Mahal casino in Atlantic City.

”I wrote a letter to my dear friend John, making him the offer,” said Trump, who was perched in his luxury box at Arthur Ashe Stadium yesterday, taking in Anna Kournikova’s match against Justine Henin at the United States Open. ”I have not heard back from him, but I think it would be a great event, great for the game and very exciting.”

First of all, where do you go first when you read Trump was watching an Anna Kournikova match? The sexist angle? The Russian angle? It’s tough!

Second, reading this Newsweek piece looking back at the saga, the entire idea seems like a non-starter, although the concept was not unprecedented in the sport:

The original event was massively important. The story, or a version of it, will soon be told in the film Battle of the Sexes—featuring Emma Stone as King and Steve Carrell as Riggs. Some 50 million Americans tuned in to watch the real-life spectacle, pitting the 29-year-old King, then at the height of her athletic powers, against Riggs, a 55-year-old former champion and a proud chauvinist who reveled in media hoopla. King made quick work of Riggs in the match, but the shift in perception of women in sports was massive, and a defining moment of the ’70s. King went on to dedicate her life to fighting for equality. For Riggs, who came out of retirement for the match, the whole thing was about money. Despite all that, the two remained good friends until his death from cancer in 1995. 

It was shot down quickly, though, with Venus and Serena’s father Richard dismissing it out of hand:

The idea burned out fast. (Neither the White House nor the Trump Organization responded to requests for comment.)

Richard Williams, father of Venus and Serena, slammed the door: ”We’re not interested.” The sisters brushed it off as silly: ”I don’t think it’s fair to put a 20-year-old against a 40-something,” Venus joked. 

McEnroe didn’t bite either, although he bristled at Venus’s joke. “This is not John McEnroe issuing a challenge,” he said at the time. “I wouldn’t waste my breath…. Sure, Venus Williams is a great woman player, but to insult somebody by saying I’m an old man or whatever, to get away with saying that? Anyone who knows anything about tennis wouldn’t do that.”

“I knew before I even walked up to their dad to talk about it, this was a nonstarter,” Roberts said. “They don’t take part in tomfoolery.”

So, seventeen years on, with a feature film forthcoming on the original Battle of the Sexes, it’s interesting to see where all of these protagonists ended up.

Since that 2000 U.S. Open, Venus and Serena have combined for 28 Grand Slam singles titles; Serena has 22 in that span. They’ve certainly managed to handle their careers just fine without a Trump-faciliated sideshow on their resumes. McEnroe remains as crotchety as ever, a man who undeniably knows tennis backwards and forwards, but can’t quite grasp the nuance required to avoid controversy when comparing sporting accomplishments.

As for Donald Trump, of course, you likely know the ending: his Trump Entertainment company filed for bankruptcy in 2014, which eventually led to the closure of the Trump Taj Mahal where this match was to have taken place.

About Jay Rigdon

Jay is a writer and editor for The Comeback, and a contributor at Awful Announcing. He is not a strong swimmer.