John McEnroe and Serena Williams enjoyed legendary tennis careers, winning 30 Grand Slam singles titles between them.
Never one to shy away from the limelight, McEnroe burst onto the scene in 1979, winning his first Major title at the US Open.
He added six more Grand Slams to his collection over the next five years, and spent a mightily impressive 170 weeks as the number-one-ranked player on the ATP Tour.
McEnroe’s fellow American, Williams, was another to win her first Slam at Flushing Meadows, doing so in 1999.
Breaking the Open Era record, Williams retired in 2022 as a 23-time Grand Slam champion, holding the top spot in the WTA rankings for 319 weeks.
Both players carved out memorable legacies in tennis, although they came close to making even more headlines 25 years ago, when Donald Trump made them an intriguing offer.
Donald Trump made an offer to set up dream match between John McEnroe and Serena Williams
Appearing on Jimmy Kimmel Live in 2015, McEnroe revealed that Trump had made an offer for him and Williams to compete in an exhibition match.
“15 years ago, Donald Trump made an offer, which I felt like was not enough, and I think he was humouring the two of us,” said McEnroe.
“Serena [Williams] has a lot to lose, by losing to an old fart like myself, and I’ve got a lot to lose, if I lose to, god forbid, a woman, I’m not allowed in any men’s locker room for the next 15 years, or possibly the end of my life, that’s part of why it’s intriguing.
“If they paid the type of money that [Manny] Pacquiao and the other guy got….”
Trump’s offer didn’t get the deal done in 2000, but McEnroe was confident that he could still beat Williams at the age of 57.
“I believe that I could still take her,” he said.
McEnroe’s bold claim came just weeks before Williams travelled to New York, looking to complete the Calendar Grand Slam.
Williams had won the Australian Open, French Open, and Wimbledon in 2015, and was just seven wins away from immortality.
Entering the tournament as the heavy favorite and number one seed, Williams advanced to the semi-finals without too much trouble.
- 2015 US Open QF – Serena Williams beat Venus Williams, 6-2, 1-6, 6-3
- 2015 US Open 4R – Serena Williams beat Madison Keys, 6-3, 6-3
- 2015 US Open 3R – Serena Williams beat Bethanie Mattek-Sands, 3-6, 7-5, 6-0
- 2015 US Open 2R – Serena Williams beat Kiki Bertens, 7-6, 6-3
- 2015 US Open 1R – Serena Williams beat Vitalia Diachenko, 6-0, 2-0 (RET)
It was there that Williams suffered one of the most shocking defeats of her entire tennis career.
In three sets, unseeded Italian Roberta Vinci beat Williams 2-6, 6-4, 6-4, stunning Arthur Ashe Stadium into silence.
Williams never came closer to completing the Calendar Grand Slam, as she came up just short in 2015, winning 26 of the 28 matches required.
However, whilst beating Vinci in the semi-finals was a step too far, we will never know how she would have fared against McEnroe.
What happened when Serena Williams played the ATP world number 203 in 1998?
Williams and her sister Venus Williams sparked controversy in 1998 when they claimed they could beat any male player ranked outside the world’s top 200.
Germany’s Karsten Braasch, ranked 203rd in the world, was up for the challenge, as the powers that be set up a match during the 1998 Australian Open.
Braasch made light work of S. Williams, winning their exhibition set 6-1, before the older of the two sisters stepped up to the plate.
Producing a similarly dominant performance, Braasch beat V. Williams 6-2, as he proved the Williams sisters wrong.
They subsequently adjusted their claim, suggesting they could beat anyone ranked outside the top 350 on the men’s tour.
During an interview with The Observer in 2001, Braasch joked he would be up for a rematch.
“Apparently, after the game, Serena [Williams] and Venus [Williams] immediately told the press they wanted to challenge a male player again. This time, they revised the ranking of the man they wanted to face to 350 in the world,” he said.
“I informed the journalist who told me this that in the next week, I was set to lose a lot of ATP points and drop down to 350 in the rankings.
“I told him that if Venus and Serena waited just one week, they could challenge me all over again!”
That rematch never came to fruition, just as Williams and McEnroe’s dream match never took place.
25 years on, we can only imagine what would have happened if Trump had made an offer too good to refuse, and the two American legends faced off in a once-in-a-lifetime clash.
