Pablo Torre Finds Out - Inside the Billionaire Shadow League Funding American Tennis

Episode Date: September 10, 2026

If you thought U.S. Open prices were bad, wait until you learn how much titans of Wall Street will pay to play with the pros. The Athletic's Matthew Futterman reports — from the bromance of Frances Tiafoe and hedge-fund king Bill Ackman, to the matchmaker of the Finance Cup and the Koch family court in the Hamptons — on how American tennis became symbiotic with a new class of mega-rich benefactors.• Read more from The Athletic: https://www.nytimes.com/athletic/7580250/bill-ackman-tennis-finance-hall-fame/ • Subscribe to The Athletic• Previously on PTFO: David Foster Wallace, Michael Joyce and the Psychology of Tennis Hosted on Acast. See acast.com/privacy for more information.

Welcome to Pablo Torre finds out. I am Pablo Torre, and today we're going to find out what this sound is. You can look at someone like Francis Tiafo making the semifinals of the U.S. Open, winning tournaments, and you can say, I help make that happen right after this. It's not surprising that tennis on some level, I should say, is like a sport for people with money. It's a country club sport by reputation, of course. And history. Yeah. But even like the U.S. Open this year, which have you been going to?

Every day. Every night. How many has it been? Matthew Futterman, and thank you for being here again, by the way. Thanks for having me. How many has it been? I started going to the, what is now called the Billy Jean King National Tennis Center when I was nine years old, opened in 1978, old Lewis Armstrong Stadium. In terms of covering it, I don't know.

I've been a sports writer for 25, 26 years, and pretty much every year. I try to go every year, and part of the thing about it is that this feels like kind of the people's open. There's crowd noise, there is cheering, there is booing, there is the city of New York almost as this character, the audience feels participatory in ways that are not Wimbledon or French opening. Yes, 100%. The U.S. Open is the...

the only Grand Slam, and it's, I would say, one of the rarer of the big tournaments, many of which take place in, like, huge diverse cities, where you walk around the crowd, it somewhat resembles the city that it exists in. Takes place in a public park, publicly owned facility, owned by the USDA, national governing body of tennis in America. They're all about accessibility, supposes. But this U.S. Open has tested their definition of accessibility in ways that I think a lot of people didn't anticipate. It is hard to get grounds pass.

There is a level now of out-of-control pricing when it comes to something that is meant for broad, popular consumption. Yeah, I would say this year what has really struck me about the U.S. Open is that I feel like I am in an area. You can very easily see that in an airport, there is part of the airport for wealthy people who don't wait on lines. Hang out at a club, baby. Hang out in the lounge. And there is the airport for everyone else who is, you know, like fighting for an outlet and waiting in like the 26-deep Starbucks line. They are currently building nine new hospitality clubs to entertain all the new club. seating they have. They actually moved

a lot of the seats down from the mid level into the lower level through this $800 million renovation they're doing on Arthraud Stadium. So they did the thing that's supposed to be impossible, which is they created more beachfront property, which they can get the most

amount of money from. And the feeling I have gotten is that this nonprofit organization, which is holding its signature an event in this public park, is suddenly like somehow fitting in with the larger story of America of income inequality and like the top 3% or whatever it is who can afford $4,000 to take a family of four to the U.S.

Open. They're having all the fun and everyone else is just sort of like fighting over the scraps. But the moment that this all came to mind wasn't this year. It was last year. It was July, and what is, I think, very safely described as one of the strangest tennis matches that anyone anywhere has ever seen. So you may have noticed that we do like following the money here on PTFO, and today's trail actually takes us from New York City, just for a minute here, and back to the great state of Rhode Island. for a professional tennis match at the Hall of Fame Open, a small but dignified tournament in Newport,

happens to be underway. These are people who are playing who are trying to get to the major leagues of tennis. There are rankings points on the line, not that many, there is some money on the line, not that much. But right now, on this July day in question, there is something big at stake. Because three of the four players on the court

are elite professional tennis players, Bernard Tomich and Omar Jaseka on one side, the recently retired Jack Sock on the other, all of these guys still in their late 20s or early 30s. But the fourth player, Jack Sox partner, a gentleman dressed in all white, is named Bill Ackman. And Bill Ackman has never played professional tennis before.

In terms of his competitive, tennis experience. I think it's safe to say that pretty much ended at Horace Gilly High School in Westchester County in New York. He did not play college tennis. He was a rower at Harvard. He's hitting the ball right into the net. Errors happen in tennis. Even the best players hit a lot of balls into the net. Yeah. But I think there's like a lack of familiarity. A lack of velocity on it. Which in fairness may also be, because at the time of this match, Bill Ackman is 59 years old.

And then you get to his surf. I can tell you it's not a serve that really belongs on the court in a professional tournament. Which makes all 67 minutes of this match inexplicable. Until you realize, perhaps, that Bill Ackman also happens to be a hedge fund manager

worth $11.7 billion. I try to have a conviction based on the facts and a kind of a key thing. If you've done a lot of work on something and you made your bet and then facts start to emerge that are inconsistent with the original thesis, you've got to rethink the bet.

I'm negative on New York if Mondami's elected, but I'm positive on the country. Clearly we have the most pro-business president we've had in a very long time. Always been a big free speech advocate. It's important for me to be able to share a bond. points of view. And the power of X is that you can reach a very broad audience of people.

I have, you know, approaching 900,000 followers, and a lot of them are members of media or CEOs, people in government. I follow him. I regret to inform my audience. He, you know, sounds off on all sorts of public policy. The master of the 5,000-word tweet is Bill Ackman, this guy. But the reason that I wanted to cover billionaire make-a-wish tennis, as I have come to understand this, is that this was not something that lots of people in real professional tennis were cool with when they saw it. Like actual professional tennis star Andy Rodic on his podcast. 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. There was exactly one person on that court trying as hard as they could, and a match where it looked like four players were in the bag. It was a disaster. And Martina and Avertilova, no less than Martina, posted on Bill Ackman's favorite platform, X. Quote, apparently you can buy yourself a wild card owe to have that confidence. End quote. But immediately, the tournament organizers said,

No, no, no, no, quote, in no way did Bill buy his way into the Hall of Fame open? They proceeded to explain that Bill Ackman and his partner, Jack Sock, they had this wildcard spot, quote, to bring further excitement to this year's tournament. Well, there was excitement about it. Guilty is charged. I was excited. I remain excited by the fact that this ever happened. It's crazy to me. At tournaments, there are spots reserved for the tournament just to hand out. Usually they go to players who might attract the crowd. I mean, Serena Williams and Venus Williams, you know, they got a doubles wild card into the U.S. Open this year. Usually these people have some resume of accomplishments in the sport.

And that's not what happened here. And that's why we're doing this episode is because I have been last. at this for a variety of reasons, one of them, how Bill Ackman defended himself on Twitter, when he said, in part, quote, what people are missing is that the whole thing worked out perfectly. My poor play dramatically increased the virality of the event, driving massively more coverage than if I had played well. End quote.

The excuse making continued, quote, Jack also chose the ad side, and I have been playing the ad side for the last year. I was also serving into the 130 p.m. Sun with a shot clock. Prentices, a new experience for me. End quote. And that's, of course, before we then get to the whole thing about how the other side was actually taking it. I mean, kid gloves is not even an appropriate descriptor of how soft, how pillowy these serves were at times.

Well, tennis actually has a word as a phrase that encapsulates this. is called customer tennis. That's so good. It's what happens when you're on the other side of the net from someone who's not as good, but might be paying you to play with him or it might be beneficial for you, not to make them feel bad or uncomfortable.

But the concept of customer tennis, which I did not know until just now, that is the theme here. This is transactional tennis. And it's not supposed to be the case that the Tennis Hall of Fame, or perhaps tennis itself writ large, is in the position of the customer. I mean, what happens is that four days after the match,

Bill Ackman announces on X that he is giving them, the Hall of Fame, a $10 million endowment, and that he would, quote, manage it for free. to which the Hall of Fame says, after some deliberation, we cannot accept your $10 million, because then it would create this perception of impropriety, which is a remarkable thing to have to say, that we're at a point where this has been so embarrassing

that for you to give us $10 million looks like this is customer tennis of an even grander scale that puts us all to shape. Yeah, it looked like a quid pro quo. happening during an actual event. That sparked a bit of outrage and crossed a line. And this is where we should point out that Bill Ackman is not just any billionaire tennis enthusiast who thinks he can play professional sports. He is particularly important in the world of tennis as, yes, the flow of money is concerned.

Yeah, he has been a huge benefactor. He's given millions of dollars to the Junior Tennis Champion Center, otherwise known as a JTCC in Washington, D.C., which produced players like Francis Tiafo and Robin Montgomery, both players that he has personally given money to in order to help launch their careers. And he's been a benefactor at the USDA Foundation. He went so far as to bankroll the Professional Tennis Players Association. Yes, Novak Djokovic six years ago was launching a player group that was supposed to sort of be about, against the control by management, the ATP.

It's like a union. Basically a union. And then also with a for-profit entity. A whole McGillah that led Bill Ackman, by the way, to say things like, quote, I understood the plight of the player, end quote. But the point here is that Bill Ackman loves tennis, funds tennis, is all over the sport in ways that someone like you has seen everywhere. Every time I turn my head, I feel like there is Ackman involvement. And he has, by the way, discussed openly that he plays with all of these excellent tennis players quite regularly.

On X, he wanted to say, quote, I regularly play with mid-20-year-old D-1 college players and recently retired pros on a familiar court with no audience. which is to say that Bill Ackman is living a life that I totally underestimated. I think what's so interesting about this experience is that while it was so crazy to you, tennis exists in this universe where we've talked about the intersection of wealth with the sport, where the system is set up and is so instituted. so that this was not so crazy to some of the people who were involved in the decision-making. The part about this to me that I didn't quite realize until we started talking is that there are more Bill Acmes. He's not alone.

There is what appears to be this entire like shadow league of tennis of Wall Street guys, these masters of the universe who are seemingly constantly surrounded by these elite tennis players, these actual former pros, these collegiate stars. And it makes it so that the world of finance and tennis are so much closer than I personally ever realized. And in ways that you didn't ever realize either. I think people are used to the idea that tennis is a wealthy person sport and they like it. But I don't think most people realize how much hang time there is between wealthy people who are not star tennis players and never were and people who were really good former NCAA champions, tour players, all of that. To the extent that those wealthy people sitting in those low seats at the U.S.

Open paying tens of thousands of dollars for those tickets, guys who are playing on the courts that they are watching, sometimes within months, sometimes within a year or two, are on the other side of the net from them. If you're the kind of sports fan who needs to go beyond the stats, and if you're the kind of sports fan, for whom, when that whistle blows, you need the deeper story, then you've got to join the Athletic Live on YouTube to hear more about all the sports stories you just cannot stop talking about. On game days, you'll watch the biggest matchups alongside some of the athletics biggest and best reporters, you know, the ones who kind of know everything going on behind the scenes.

And you can even become part of the show thanks to the interactive chat. The Athletic Live is presented by Google Gemini. Check it out now starting September 8th. And subscribe now on YouTube. We're using you, Matt, as a guide into a world that I did not know about, a subculture, a corner of tennis that seems to explain what we are seeing when we were watching tennis now on television. but it's happening not far from here. I mean, it's sort of originating on Wall Street here in downtown Manhattan.

And the ways that the ultra-rich are connecting to all of these elite tennis players, it brings us to a particular Wall Street figure who's sort of like the nexus point of this world. And his name is... Jeff Appel. Otherwise known as... The mayor of New York tennis.

AKA the guy responsible for why Bill Ackman is somebody that I've been thinking about for the last year. My name is Jeff Appel. Thank you for having me today. I started playing competitively since I was about nine or ten years old. I've been exposed to a lot, but I'd have to say that as good as a tennis player, some people think I am, I think I'm better off the court. And sort of my contributions to the sport is... What is Jeff Appel's day job, Matt?

He runs an investment fund called JDA Funds Management. I think he'd be the first to tell you. He's sort of on the back nine of his finance career. He's really into tennis and really into tennis players getting into finance. He's the guy whose bio, when you find it, lists that he's advising these SPACs and arranged an $800 million merger. And, yeah, all these eight-figure transactions for VC funds and litigation finance companies and all of that. But that's not why he's the mayor of New York Times.

No, he's the mayor of New York tennis because every week, sometimes more than every week, he's organizing tennis matches on Reynolds Island with some of the best tennis players in the city, people who were top players in college, some of them play professional tennis, and there's this intermingling of quality club players, but also actual former pros. which is precisely how one Bill Ackman gets involved in this world in the first place. Ackman is invited by Jeff Appel to this Sunday morning game to play with him and a player Kyle Cleggerman. I sent Bill an unsolicited email inviting him to play tennis, you know, talking about my tennis background and Kyle's background.

And coincidentally, he responded two hours later. Bill hadn't picked up a racket since high school. What we didn't know is... So his skill, it seems to me, is that he is an expert matchmaker. He is the matchmaker that is bringing together Wall Street Titans and terrific tennis players

who may one day become Wall Street Titans. Which brings us now to something called the Finance Cup. Excellence, determination, and work ethic. All key. elements required to excel in finance and tennis. And the two fields joined together yet again for the 2003 Finance Cup as the action starts now at the Miami Beach Tennis Center.

This is the sort of full flowering of these Sunday morning games that are happening in New York. The idea is essentially a. Finance World Rider Cup of Tennis, the U.S. versus Europe, your best bankers and former pros against our best bankers and former pros. I'm so perversely interested in what this is like. I would say one of the ultimate networking events, given that many of the people who have come through the finance cup beginning when they're right out of college, or shortly thereafter have gone on to run like major, major Wall Street institutions and hedge funds.

As they alternate locations between the U.S. and Europe this June, by the way, Marbella Spain, at Rafa Nadal's Academy, this whole thing has a trophy. Have you seen the trophy? Yeah, it's pretty nice trophy. In fact, it's crafted from English Oak, according to the Instagram page I found for it. And it's also, though, a bear and a bull. fused together into this almost mythological creature that speaks directly to, yes, the provenance of bear and bull markets. And in 2025, it turns out, this event happened to be hosted at the Tennis Hall of Fame in Newport, Rhode Island. Ten years in, you know, we got to look like a real company. It's a special event. You know, there aren't that many opportunities.

where you get to go hang out with a bunch of wonderful people for a long weekend, playing an amazing sport. We're all incredibly passionate about. And people from all the world come to this spectacular city. Newport is amazing. Who thinks Newport's amazing? Now it's all coming together now, isn't it? Where we began our story, except we didn't mention when we began our story that it happened to also involve a Gatsby-themed black tie event at the historic Marble House Mansion. in Newport.

That's tennis, isn't it? This is what makes this sport different from all other sports, I would argue. How would you describe, actually, if you were to sort of give us a taxonomy of wealth in sports, what does strike you as like texturally distinct to tennis as a matter of how they are moneyed?

I would say it's the participatory aspect of it. What do you mean? In tennis, I think what happens because it's, It's one-on-one. It's because you need a partner. There's a situation where the illusion can get created that, like, I'm actually playing with this guy. We're a team.

We're a team or we're hitting partners and I'm hitting balls and I'm hitting well today. And he's moving me around and I'm moving him around a little bit. And that thing that we mentioned before, that whole concept of, like, customer tennis, that can be forgotten. Well, in the Finance Cup, to that point, one of the regulations that governs who can participate is that you got to work full time in finance, which is to say that all of these elite players that you've referenced are all finance guys now. Yeah. Yeah. They are actually on these teams in a corporate sense. Yeah, ringers don't exist.

You can't rock up there with Patrick McEnroe. No, you can be a former ATP number three, but you got to actually earn your corporate sleeveless vest, your fleece vest. You earn that. And Jeff Appel doesn't only put you in games. He and a couple of other people become your mentors and nurse your career. And it's why you want to keep showing up in those games on Sunday morning. And it's why you want to play in the finance cup. You don't play tennis all day. You also do a lot of. out of networking in an atmosphere like that. People don't know this, but Andres Pedrosa, the most successful coach in college tennis. In 2005, he worked at Bear Stearns, okay? I know Andres from when he was still playing on tour and had a hand in his brief and successful Wall Street career.

Jared Donaldson's another great example. Someone I've been involved in since he's 19 years old. He didn't like hanging out with the tennis players. He liked hanging out with business people and just, like business. I went back to school after three knee surgeries. He was at Fortress. Now he's starting at Ballyasney in the capital markets. Gary Donaldson, by the way, the guy who made five grants lambs was ranked as high as 48 in the world in 2018. Yeah, but not that into it, apparently. He always wanted another career. You find that with a lot of tennis players.

I think I've done it maybe, you know, 100, 150 times of opening up some doors and coaching them in terms of what's the right fit for them and their comparative advantage, right? If someone's a big personality and doesn't have a long attention span, they're more better geared toward wealth management or the capital markets as opposed to the deep analysis and the perhaps perfect example of this that I want to focus on with you now is Milos Rownich. So how much tennis are you playing now, Milos? Not much. Former Wimbledon finalists, one of the scariest

serves in the game. For many years, the last guy you wanted to see next to your name on a draw sheet early in a tournament, because he could literally take the racket out of your hand. And now, he's taking

the money out of someone else's because he works at Goldman Sachs. I knew I always wanted to do something very different after tennis, and then got this opportunity here at Goldman and jumped on it right away and I was very excited about it and it's great because I'm learning a lot.

So now I sit on the external investing group on the private equity focus team and it's been a few adjustments along the way but it's definitely like exactly where I want to be and I'm getting close to that path. And he isn't alone, it turns out. Just last week at the U.S. Open, former world number six, Gail Monfie,

foreshadowed his own life after retirement. So far, to be honest, I have a new chapter coming next year. I will work in finance. You know, I already designed to work in the wealth management in a Swiss company. So my next chapter looking more in the office and working in finance. What did tennis players specifically have to offer the world of Wall Street, do you think? Tennis is not easy. Right, right.

Tennis is a grind. Tennis has always sort of reminded me of, like, boxing. There's an appreciation for the soft skill of athletes that doesn't necessarily show on a resume, but there's just like that intensity that comes with it, the resilience just also being okay. with like failure in getting up again and trying again. And in addition to the extent that like the world of finance can become something of a jungle at times and rather combative, tennis is very similar in the sense that it is non-contact combat, but there's plenty of battling.

I think the one mistake you can make is thinking like just because I was a good tennis player, I'll be good at the next thing or I deserve an opportunity and it doesn't work that way. I took 342 meetings with different people, all unique meetings, to like get in front of as many people as I can, learn as much as I can, and see where I can get an opportunity to, like, get a shot. And trust me, out of 142, there's a lot of like, hey, we think we're interested or we think we can help you. But then when it comes push to shove, it's like a different thing, right? The jobs that used to exist for former tennis players. in the financial world where you just kind of hang around

and you get trotted out to play with clients and show up and show up at dinner. Glad hand. Yeah. Those jobs don't really exist anymore. And I think Milo should be the first one to tell you because he had a lot of doors closed.

He had all those meetings, but he only got one job. I like that he remembers that he had 342 of them. Yeah, not 346. That's kind of like how every wide receiver knows how many players were drafted ahead of him. Yeah, right.

He's hanging on to how hard it took to get to the finals of Wimbledon in 2016. He's got the receipts for it. And the symbiosis of how these skill sets sort of collide and then swap sometimes. I'm thinking of how these bankers also fancy themselves tennis scouts. In some ways, yeah, because they are solicit. for help for really promising tennis players who might not have the means to afford what is incredibly expensive sport. I mean, tennis, if you're a kid, is going to cost you like $50,000 a year to develop

as a top tennis player. So what happens is people like Bill Ackman get solicited at times and say, can you help out this kid? It happened to Kogo-Goff when the USDA Foundation was able to... send some money to her family in order to get her an extra trainer. And Ackman famously funded the early stages of careers like Francis Tiafos and Robin Montgomery, too. It's so funny, even just how you put it, though, being an early stage investor in Francis Tiafo is almost literally investing.

Yeah, it doesn't pay financial dividends. That is not what they're in it for. There are parts of the world where that happens, and it can get a lot of players in. into some trouble, especially when they aren't able to fulfill and pay back those investments. That is not this at all. This has a different sort of payoff. You can look at someone like Francis Tiafo making the semifinals of the U.S. Open, winning tournaments, and you can say, I help make that happen. It was a great guy. You know, he's done so well in life. And the fact that he wants to give

back to young, young athletes like me, it's unbelievable. He gave me. He gave me a great guy. He gave me I mean, he's done so much for me. I mean, he gave me a chance to play around the world and not worry about any finances at all. You can be text buddies with him for the rest of your life. You can be on email threads. Jeff Appel and Bill Ackman and Robin Montgomery are, as we speak, talking about, you know, her progress.

He wins a match. You send her a note of support. Benefactors. Yeah, you're a benefactor. It makes it, you know, and that happens in all walks of life. I think it probably happens more in tennis than in just about any other sport that I've ever seen. And in this case, what you're saying is that Ackman, he is generous in real ways. In exchange, he gets to hang.

It's one of those, both things can be true, as I think is often true with any kind of philanthropy. Yes, yes, yes. It makes us feel good about ourselves. You know, we get something out of it. Humans get something out of being charitable. It's the Kirby Enthusiasm episode in which Larry David is wondering about being an anonymous donor. It's like, well, why would you do that? And in this case, by the way, what Bill Ackman and his colleagues who have estates,

and we're here talking about venture capitalists like Michael Loeb, we're talking about Julia Koch and the Coke estate, speaking of the complications of philanthropies, philanthropy. Here we're talking, though, about hosts, hosts of actual tennis matches on their properties. Yeah, practice tennis matches in the case of, you know, the COCA state where I've been to interview players and watch some practice matches. What's that house like? Henry Moore's sculptures, jacometti sculptures. I mean, really just, uh, you know, one of the grand properties in Southampton. This is one of the things that happens like the week before the U.S. Open on the highest level

where, you know, you can go out there and, you know, Yonik Sinner staying in Bridge Hampton and Tommy Paul is in Southampton. And it's funny because there's only a handful of courts that have enough room in the backcourt to be able to accommodate these. professional players. You're saying not all billionaire tennis courts are created equal. Not all billionaire tennis courts are created equal. One of the advantages of the coca state is that there is enough room, not surprisingly,

behind the baseline so that the best tennis players in the world can hit the kickiest kick serve and the guy on the other side of the net will not run into the back fence. I am looking at photos of the coca state. and they got room for all sorts of things. Including a nice big tennis court where some of the best players in the world, Hall of Fame members, have played and stayed. And yeah, I mean, if you want to talk about tennis benefactors,

Julie Coke is right up there. Also, one of the things that the JTCC does every year is they bring some of the really promising kids from their academy out to the east end of Long Island. So Robin Montgomery, I was speaking with her after she won a doubles match at the U.S. Open, and I was asking her about what it was like being a kid,

because she was one of those kids who got brought up to the east end of Long Island. She grew up in Washington, D.C., in a one-bedroom apartment with her mother and a grandmother. And she told me of going up to the Hamptons for a weekend to meet some of these people and sort of show people who donate money to organizations like this, like where their money was going.

And she recalled like being in a car and driving around there and with her friend thinking like, why are these driveways so long? I mean, it was a completely different world of anything she had seen. Francis Tiafo was one of the kids who made that trip. He told me, he just described it as just a completely different world. eye-opener. He had never seen or kind of imagined houses like that. And to be on their properties was yet, you know, a crazy experience for him in his words. And he met Ackman and

changed his life. Which is all to say that when you understand where Bill Ackman's money, in part, is going, which is to fund the pipeline of American youth tennis. This is something that American tennis in general really relies on. Like, he's important to the premise that we're even competitive as a country. Because what separates America from most countries is these sports federations, they don't receive government support. They have to raise money themselves in order to fund their operations. It is why one of them got to play in a professional tennis match

at the Tennis Hall of Fame, one might argue, in Newport, Rhode Island. Yeah, it's a big reason. So I have to admit that in my delight at how horrific Bill Ackman was in his lone professional tennis experience, you have pointed out that actually Bill Ackman's scouting report is not quite as I have conveyed it. Yeah, I mean, to be clear, he's a pretty good tennis player by all accounts. his favorite partner's guy named

Richie Renenberg. Richie Rennerberg, I spent 13 years on the professional tennis tour from 1987 to 2000. Former pro, U.S. Open doubles champ, good player. There is a version of Richie Renenberg that Bill Ackman can legitimately hang with on a tennis court,

especially if he's his partner. Bill's a very good play. He's a very good technique. I would say that he likes the faster courts, you know, so the grass courts suited him pretty well. I remember seeing him at an event. I didn't know him probably 20 years ago. There are these Michael Milken pro-ams. And he was okay.

He wasn't great, to be honest. And then he worked at it, and he plays a ton. So I'd say the strengths of his game where his serve is very good. His neck game is exceptionally good. He covers a lot of court. He's a big guy. And his grounds, like all of us, you know, days where he's hitting him really well, he returns and days where he's not.

But then I ask people. like Milo's Rounditch, who has played in this finance cup and has been across other tennis courts with Bill Ackman, like what he does? And I was like, you know, are you bringing the fastball? You kind of learn this ability to just adjust to make sure everybody's having as good of a time as possible. Sometimes the fun part is people do want to get aced, right? People do want to see that big serve and kind of get the feeling of how quickly that passes by. So sometimes that's a fun of it. The other times it's, hey, people, if you're playing with somebody for an hour and a half, they don't only want to do that.

Sometimes they want to get into some rallies. They want to get some exercise out of it. And I asked Richie Renenberg, like, who has, you know, for 30 years played with wealthy people. Originally, they brought him into the finance world. Ken Brody, who had been a top advisor to Bill Clinton, he was Richie Renenberg's entree into finance. And I asked him, like, well, what do you do when you're playing a guy like that who's really into tennis. One thing you do is you try to put the ball in a good spot. You're not hitting heavy top and throwing them up against the fence. You're not doing that. So what you come to understand

is that idea of levels, the idea of customer tennis, and that, you know, the delusion that can take place. And so do the people in Bill Ackman's life, were they supportive of the experiment? Do they want him to do this? I asked Francis Tiafo, who has hit with him not in a while I asked him what he thought of it and he said he actually really wanted Bill to play that match and I said why and he just

had a big smile and I said why did you want him to see what the actual level was like he wanted Bill Ackman to find out yeah and he just had a big big smile so he was good with it for his own reasons and even his buddy Richie Wrennenberg

you know he understands that there are limits, you know? And I think it's telling sort of like what his reaction is when we ask him about Atman's skill. I remember not long after I got there, Bill's coaches, Georgie and Olivier, come over and say, they just gave Bill and Walcott

into the challenger. And I'm like, what? I actually thought that's kind of cool. I mean, he's been talking about maybe getting a Welkron little challenger here, a challenger there. So we started talking about partners and people he might play with.

And at one point, he kind of said, would you want to play? And I said, Bill, no. I mean, you need somebody. Because with playing with me, we could easily lose love and love. So I said, you need somebody who you can at least get a game with. So does to translate that, though? Ritchie Rennonberg, literal 1992 U.S. Open doubles champion, is like,

I am not good enough to help you stay on this court. In a minor league tennis match. This is where I just got to return, of course, to the Everything app, X, because a week before the match what Bill Ackman posted on July 2nd quote, if we win, I am pretty sure I will be the oldest person

in tennis history at 59 to win ATP points. I am playing the best tennis of my life. And Jack, this is Jack Sock, his actual eventual doubles partner, Jack is one of the greatest double players ever. He won at Wimbledon and the at US Open

and a gold medal in Olympics. And we start practice this Friday, so you never know, end quote. So we know what, ultimately happened. Yes. And I think like one of the big questions hanging out there is like, would you ever do it again? That's even on the table?

What it puts on the table is like, what was the learning experience for you? What lessons? What was the lessons you took from these 67 minutes on the tennis court? The thing about tennis and really all sports and really lots of sports. and really lots of parts of life is that your greatest strength can also be your greatest weakness. So like courage and bravado

and seeing possibility where no one else sees it is probably like Blackman's greatest strength. It allows him to make bets on things where everyone thinks he's completely crazy. Right, right. Now Bill didn't want to talk to us for this episode. Which remains very disappointing.

Yeah, I always want to. to talk to people I'm writing about. Especially, I'd imagine, if that person's stated investing philosophy is, once again, this. I try to have a conviction based on the facts and a kind of a key thing. If you've done a lot of work on something and you made your bet and then facts start to emerge that are inconsistent with the original thesis, you've got to rethink the bet. So I had to ask his friends, like, what do you think he would do if he did it again? And I asked the guy who brought him into tennis in the first place in his adult life,

figured he'd know better than anyone since he's played with him so much and talks to him all the time. And Jeff Appel said, don't bet against it happening. I don't want to speak for Bill, but he's not a man to back down from any challenge. If someone had asked you to play that day, would you have played? Fuck yeah. Really? 100%. Unfortunately, I had a tear on my part.

plancha fascia so I couldn't have played. I've never said no to a challenge on the tennis court. Even in that answer, it's like if I hadn't tore my, I'm just like, oh my, my goodness. Yeah, I was kind of amazed because, I mean, Jeff really does know about levels, but, you know, it's that thing, I guess, that everyone wants to stand in the batter's box and see what a fastball actually looks like. Could I hit the Nolan Ryan fastball? No. No. Of course. Of course not. No, and you'd be lucky to get out of there alive. I mean, that's what's amazing to me.

But this is what this story became all about. How does the mind go to a place where it's okay to play this tennis match? And it's all wrapped up in money and philanthropy and this sport that has this intersection that I think doesn't exist anywhere else. What is so reassuring is the total shock, back to reality, of there is a distinction in terms of what my money does not buy me. Yeah, you probably shouldn't be on the court. It's the complete flaw of the whole 10,000 hours idea. Yes, yes. Which is that, you know, is it nurture or nature?

Like, there's a lot of nature involved, you know. It really is. I mean, and you can get to a certain point. I mean, your development, if you're, you know, getting help and taking lessons and do all those things. But, you know, you are different from these people. You can fund the sport. You could invest in the prospects. You could enable the entire premise that America is a plausible tennis country on your giant mansion.

But the thing you can't buy is the... actual ability to hang on a court with real professional athletes. It's sort of the equivalent of, you know, making a lot of jokes and there's people around you that are laughing at them all the time. And you start to think that like, wow, I must really be funny. Yeah. You know, what happened on that court in Newport, Rhode Island, is that person went to do stand-up. Yes. And it didn't go so well. What I'm here to tell you is that what I found out is that it was f***ing hilarious.

This has been Pablo Torre finds out, a Metal Arc Media production. And I'll talk to you next time.