Bulwark Takes - We Can't Stop Laughing At Billionaire Bill Ackman's Horrible Pro-Tennis Debut

Episode Date: July 17, 2025

JVL and Ben Parker break down the bizarre and cringeworthy saga of billionaire investor Bill Ackman playing in a professional tennis tournament. Despite having no prior pro matches and being 59 years old, Ackman secured a spot in the Newport Hall of Fame Challenger event, thanks to a wildcard invite from former tennis pro Jack Sock. Ackman's poor performance, dumping serves, and hitting wildly off-target shots, was both painful and hilarious. Beyond the comedy, they emphasize the real issue: Ackman took a spot from a legitimate, hardworking player trying to climb the ranks in a brutally competitive system. This as a case study in billionaire entitlement, comparing it to fantasy camp for the ultra-rich and even likening Ackman to a “Make-A-Wish” recipient for grown men with money and delusions.

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Ba-da-ba-ba-ba. Hello everyone, this is JVL here with my bulwark colleague Ben Parker. If you like the shameful joy, then my friends, do I have a story for you. It is story time at the ranch and today we're going to talk about the ballad of Bill Ackman. Billionaire, Harvard hater, woke fighter, professional tennis player. Hmm. Hmm. Ben, give me a level set.

Hmm. Ben, give me a level set. How much do you know about tennis and or Bill Ackman and or the intersection of professional tennis and Bill Ackman? So, OK, in order tennis, it's like giant ping pong, but you can play it with more people. OK. Bill Ackman is one of these like crazy billionaire types, maybe sort of tech adjacent. I don't know who has nothing better to do but post crazy stuff on Twitter. He spends a lot of time on Twitter for a guy's worth $10 billion that dude posts. I can tell you because I've been going through his Twitter timeline and holy shit. And job must be pretty easy.

You know, it's the first 10 billion that are hard after that. You know, what I know of the intersection of the two of them is that I've seen some clips of Ackman playing tennis on Twitter that are, I'm not a tennis aficionado as you can tell, but breathtaking, just beautiful. Breathtaking as they would say on Seinfeld, yes. So here's what happened.

We had the Newport, the tennis hall of fame in America is in Newport, Rhode Island. They do a professional tournament there, it's grass courts that I think I think it's the only grass court tournament held in the United States. And it's it's not an ATP level event. The Challenger Circuit, which is like the minor leagues and. Bill Ackman played in the doubles draw recently. He's 59 years old.

He has never played a single professional tennis match. How you might say, did he get into this thing? And what happened was Jack Sock, who was a member of the last class of very good American players, I think he got his highest number 10 in the world, won a couple doubles Grand Slams. He had requested a wild card and he retired in

2023, but he requested a wild card entry into the Newport Hall of Fame open. And then he reached out to Bill Ackman and said, somebody who by all accounts, the two had never met before and said, would you like to accounts, the two had never met before, and said, would you like to be my doubles partner for this professional tennis event? Bill Ackman said, yeah, yeah, I'd love that. So you have to understand Bill Ackman is a tennis hanger on. He's the kind of guy who gives a lot of money to tennis and hangs around the sport and is just loves it, loves it so much.

Does anything he can to get as close to it as he can. And that's fine. This is, you know, there are certain rich people subcultures, I think yachting, mountaineering, Broadway. Broadway is like this. You get people who become, rich people in New York who become producers of Broadway shows, which means they just, you know, somebody has an idea for a show and they say, can you give me $5 million to do my show? And you'll be a producer. Yeah.

Bill Ackman is like that for tennis. And he has always wanted to play professionally, thinks he's pretty good. He said before the open that he is playing at 59, the best tennis of his life, which itself should be a tell, because it's either not true. It's either not true. Or if it is true, then it's just he has no business being near a professional tennis court, right? Maybe he is better now. Being near the local country club. Like the man is a danger to himself and others it looks like. So, uh, so he shows up and the, this is, you know, again, it's a small tournament. There's, you know, I think there's a thousand people there and, uh, he and Jack Sock get run off the court and it's bad.

Uh, it's real bad. So Bill Ackman, and I want to, you know, I'm a little bit of a tennis nerd myself, never a good tennis player. I've always a very bad tennis player. I'm still a very bad tennis player, hoping that by age 59, I'll be playing the best tennis of my life. That'd be really exciting. And so when you, when you look at this, you see him dumping serves into the middle of the net and, you know, hitting balls three feet wide and can't even really hold the ball. It's a bet. But here's what I want people to understand.

When I say that he has no business being near a professional tennis court, he doesn't have any business being near a high school varsity tennis court. I would say most high school, I would say your average high school singles player, either boy or girl, would probably beat him. You're just sort of average varsity team singles player. And Andy Roddick, who went off on this, on his podcast, said, there are 50 guys at my club who could beat him. Can I ask you a tennis question?

Yeah, go ahead. So I can't tell from watching the video, is the problem just like he's 59, he doesn't move very well, is the problem conditioning and he can't keep up with the players or is the problem just that his technique is awful? Just skill. Just skill. Okay. Doesn't, you can't hit the ball hard enough, can't impart enough spin, can't react quickly enough. I mean, the answer is all of the things.

Can't volley, can't return, can't serve. Literally all of the things. And as you will see in some of these shots, the guys they are playing against are clearly so freaked out by this that they are just lolly popping the ball back to him. I mean, they're they are playing with him the way I play with my eight year old, which is to just, you know, hey, come on, we'll put it right back. I'm going to try to put it where you can reach it. And maybe we'll be able to, you know, and it's it's painful to watch.

And this is all bad. But it's only it's painful to watch. And this is all bad, but it's only sad, bad, right? Like you look at him and you're like, okay, this is like make a wish, but for a billionaire, you know, he's a really rich guy. He's worked so hard his whole life. And before the world passes him by, he just wants to play professional tennis for one hour to see what it's like. Doesn't that terrible, right? Doesn't he deserve to get something after all, he's worked so hard and he's created so much wealth for everybody else. The problem is that in the aftermath of this, Bill Ackman is not either chagrined or grateful

or understanding that people are upset. He's got to be embarrassed, right? He's not embarrassed. And I want to explain why people are upset. The reason people are upset. He's not embarrassed. And I want to explain why people are upset. The reason people are upset. So tennis has all sorts of layers that are between recreational tennis and professional tennis. And so there are exhibition events, there are Pro-Am events, there are bazillion Pro-Am events where they put some, you know, local celebrity or somebody playing with a retired pro or something, and they do it for charity and it's a lot of fun. This is not that, this is a challenger circuit.

And so what you get is you get a lot of guys who are grinding it out, trying to create a career and every spot in a challenge or draw, those things are precious. Like the guys who are playing those things are desperate just to get invited into the draw. Because once you're there, you can win enough money to maybe buy your plane ticket to the next weekend. And B, there are ranking points. And this is what all these guys are chasing is points. Because you want to get enough points that you can move up into the ATP tour, which is where the real money is. And so, you know, there are thousands of guys who you and I have never heard of, who are some of the best players on the planet, and who are so good that like when you if you

stand in front of them and watch your eyes would fall out of your head, and they're scraping and sleeping in their cars and just trying to get by to get an extra point out of one of these challenges. And so Bill Ackman took a spot from somebody who has a real career or is trying to make a real career. Just kicked someone off the bottom rung of the ladder. Yes, yes. Great, lovely.

But here's the thing, Ben. When it was all over, Bill Ackman was defiant. He said that the reason, first of all, he said, I play with guys who are in their mid-20s who are Division One players or retired professionals all the time. So I know what this is like. And it's just that he had a little stage fright. He got a little stage fright. His nerves, he had butterflies in his tummy, Ben. Tummy flies.

And so he just, he felt like he was short of breath and he was hitting balls short and he didn't, it wasn't a fitness thing. He was short of breath. Again, I choose to believe him. Oh, oh, oh. And you know, he, and also didn't, it wasn't a fitness thing. He was short of breath. Again, I choose to believe him. Oh, oh, oh. And you know, he, and also the sun, it was 1.30 in the afternoon, he says, and so the sun was a real problem

that he was trying to serve the sun. Also, he, for the last year, has been only playing the ad side in doubles, and Jack Sock called the ad side. And so all of a sudden, Bill had to play the do side, and how can all of a sudden Bill had to play the due side. And how can you expect him to know how to play the due side? That's really hard. It's like, you might as well ask him to play left handed and,

and then Ben, he says, and actually we almost had them. How close was it? His tennis scores are weird. Explain this to me. So, they dropped the first set very badly. I think it was 6-1. And in the second set, he said, you know, we were up a break, and then we had three break points. And if we had won one of those break points, then we probably would have won the second set. And then we would have had all the momentum in the world going into the third set. So if you think about it, we kind of won.

Because if he had won, then he would have probably won, is his logic. Am I following that right? Yeah, basically they were right there. They're right there. The whole thing is and oh, and then he also said it was extra hard because the other players were taking it easy on him. And that really threw him off. So the levels of self delusion here, and I want to, again, for people who aren't like into tennis culture, I am positive that it is true that a guy who's worth $10 billion has very often played with guys who are, you know, retired college players and retired pros. Because if somebody who's worth $10 billion says to you, hey, you

want to come and hit around with me? And you've got a charity or something, then you say, yeah, sure, I'll come and come over to your club and hit with you for an hour. Hitting around with these guys does not mean that he has played against these guys. And he seems to have no sense of that. He seems to feel like, yeah, you know, I went out and hit around with this guy who was third singles for University of Nebraska once and, you know, I felt like I was really hanging with him there. It's like that episode of 30 Rock. It's like that episode of 30 Rock

where John Hamm gets to do whatever he wants because he's good looking and he's like flying planes and in surgery. And he thinks that he's the best at everything and he's actually an idiot. And he's just really good looking. Some people are like, oh yeah, you're doing great. Oh, it's a great appendectomy.

It's exactly like that. It's are like, oh, yeah, you're doing great. Oh, it's a great appendectomy. It's exactly like it's like that. But with 10 billion dollars. And it's I've I've never seen anything quite like it. And I that level of self delusion. Again, I'm not we joke around here that I'm the house communist and I'm not actually a communist. I'm really like a one and a half cheers for capitalism guy. But you look at dudes like Bill Ackman and it's real hard not to go full

bullshy. I mean, my reaction is, uh, man, it's a real shame he didn't have this kind of, uh, passion for the NFL. MMA. If only he had tried, if only Bill Ackman had tried MMA, cause there's, you know, there is a long list of, of people who've decided, Oh yeah, you know, I'm, I'm a real tough guy. I work out, I work out in a dojo. I think I'll try MMA. And then they just like get their asses beat.

Um, it would have been great. Would have been awesome. Bill Ackman had tried MMA. You know what? Hope Springs Eternal. Maybe he'll do it. Maybe he will do the bicentennial or quadricentennial MMA fight at the White House.

At the White House. Is that too much to hope? Is it too much to hope that we can get Conor McGregor versus Bill Ackman in the octagon on the White House? At the White House. Is that too much to hope? Is it too much to hope that we can get Conor McGregor versus Bill Ackman in the octagon on the White House lawn? We can only pray. Good luck, America. There's a time and a place for a filet of fish, but breakfast is for sausage biscuits.

McDonald's breakfast comes first.