Remember how last year in December, Diego Forlán, a 45-year-old former soccer player, made his pro tennis debut? After five years of retirement from soccer, he was seen competing at the Uruguay Open in a doubles match. The celebrated striker of his time received a warm reception from a packed crowd. Sadly, he couldn’t win this encounter. Along with his partner Federico Cori, he lost against the pair of Boris Arias and Federico Zeballos in the first round of the ATP Challenger event in his home city of Montevideo. Fast forward to July 2025, and we have a nearly 60-year-old businessman trying a similar luck. The only difference? He’s actually not a sports person like Forlán. But hey, Bill Ackman still managed to make his pro tennis debut on Wednesday. However, the aftermath of him accomplishing an ATP dream has been anything but positive. Former tennis icon Andy Roddick is annoyed at the Hall of Fame for this “joke”.

After making his ATP debut, billionaire Bill Ackman, a 59-year-old hedge fund manager, played at the Hall of Fame Open, a Challenger tournament in Newport, Rhode Island. On July 9, he appeared in a doubles match. His partner was an ex-American pro and Olympics Gold medalist, Jack Sock. They were up against Australians Omar Jasika and Bernard Tomic. Well, Ackman’s ‘dream debut’ didn’t prove to be fruitful enough. He and Sock lost in straight sets (1-6, 5-7) to Jasika and Tomic.

Now, out of these four players competing, only Ackman was the odd one out. Anyone can tell. That’s what the 2003 US Open winner Andy Roddick has suggested in his brutal response to Hall of Fame. Why? For letting the CEO of Pershing Square Capital Management play in a Challenger event. A professional platform that normally allows actual players to get better. During an episode of his Served podcast, Roddick minced no words in slamming the Hall of Fame officials to have Ackman, 59, compete at such serious level. He began saying, “Bill Ackman who’s been a massive tennis fan, supporter, funds the PTPA, does the whole thing. Wanted to play a pro tournament. So, obviously some exchange of something, like you don’t give a wild card to someone who 50 players at my club are better than.”

Roddick underlined that he truly respects the Hall of Fame, being an inductee himself. But when it comes to Ackman’s case, “This was a total miss.” Reason? “The job of the Hall of Fame is to preserve and celebrate excellence in our sport. This was the biggest joke I’ve ever watched in professional tennis.”

He simply called it “a disaster”. and went on to mention, “Now I can’t tell people, you can make your own decisions. I’m sure sponsors are tough for Challengers, I get it. This was beneath the Hall of Fame in my opinion. It’s nothing personal against Bill Ackman. He can do whatever he wants. If his dream was to do it and someone’s going to let him do it, I mean it’s not his fault. I don’t blame him.”

Well, Roddick has his own views and rightfully so. On the other hand, however, Ackman must be feeling amazing after fulfilling his tennis dream. But one may still wonder: how come he developed a deep passion for tennis in the first place?

A $4 billion blunder that resulted in Bill Ackman going back to his tennis dream

The hedge fund manager’s interest for tennis has been brewing for years. In fact, he was fond of tennis since his childhood. He grew up in Chappaqua, New York, where he played competitively at the Horace Greeley High School in early 1980s. Even after he went into a different profession, Ackman never left his passion for the sport. At one point, he even desired to make a court on the rooftop of his Manhattan office. It’s been revealed that he trains daily, for about 90 minutes a day during summers.

In the early 2010s, he had icons like Andre Agassi and Pete Sampras compete in his charity event at the Madison Square Garden. Later, Ackman even claimed that he defeated Agassi in a casual doubles game.

But in 2015, his life took a turn, costing him $4 billion along the way. Riding high on past wins, he took a huge swing at Valeant Pharmaceuticals. Ackman believed its bold business model of acquiring tiny drug companies and increasing prices was the ultimate future of pharma. For that, he was looked upon as a genius for a momentary period. But guess what? There were some mysterious findings that emerged later.

It was found that he had connections with a mail-order drugstore named Philidor. Further, immensely increased drug prices were met with harsh criticism publicly. Not to mention an investigation by the SEC and Congress. But Ackman didn’t back out. He tried to turn the tide around in his favor, even becoming a board member of the company. But nothing worked out.

The stock plummeted from $260 to less than $11 in the year 2017. And Ackman? Well, he exited while leaving one of the costliest bets in hedge fund history. Later, he made a confession saying it was “one very big mistake,” that probably reminded him that tennis, not trading floor, was his real passion in the first place.

What are your honest thoughts on Ackman’s tennis debut at the Hall of Fame Open? Let us know in the comments below.