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John McEnroe: Donald Trump Offered Me $1 million to Play Serena Williams

How much would you pay to put on a modern-day Battle of the Sexes tennis match? According to tennis great John McEnroe, Donald Trump was willing pay $1 million. On Wednesday, McEnroe was interviewed on “In Depth with Graham Bensinger,” and revealed that 18 years ago, the not-yet-president offered him a decent chunk of change to play either Serena Williams or Venus Williams.

The strangest Dear John letter ever

According to McEnroe, he got an envelope while he was calling a match in 1998. It was from Donald Trump, who McEnroe was definitely aware of at the time — he called Trump a “promoter galore.” McEnroe remembers the general gist of the letter.

“‘Dear John, I want to offer you $1 million to play either Serena or Venus.’”

Why Serena or Venus Williams?

In 1998, the sisters were in their late teens. Serena was still establishing herself as a professional, while Venus was experiencing some early success. But being young didn’t stop them from being confident about their talent. At the Australian Open that year, the sisters both said that they could beat any male tennis player ranked outside of the top 200.

It’s likely that Trump was responding to that very bold claim by the Williams sisters. Both Venus and Serena did participate in a Battle of the Sexes match at the Australian Open that year, facing German tennis player Karsten Braasch. Even though Braasch was famous for barely training (and doing more smoking and drinking instead), they both lost. A match between 1998 John McEnroe and the teenage Williams sisters would have probably been a bloodbath.

Venus Williams (L) and her sister Serena of the U.S. celebrate their victory in the doubles finals against Mariaan de Swardt of South Africa and Elena Tatarkova of the Ukraine at the European indoor championships in Kloten October 18. The Williams sisters won 5-7 6-1 6-3.
MUE/MR/AA

McEnroe was confident, but he turned Trump down

McEnroe wasn’t sure why Trump picked him as the guy who could beat one of the Williams sisters, but he turned it down. He said that he never had a desire to play a woman and recreate a Battle of the Sexes match. He was confident he could have done it at the time, but his kids have a slightly different opinion.

“Over the course of time, literally my kids, my daughters will say: ‘Dad I don’t know if you can beat Serena.’ I’m like, ‘God I can’t even get my kids on my side.’”

Eighteen years ago, they were most likely wrong. But if they said that about their 59-year-old father last week? Well, they’re probably more right than wrong.

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