Inside the Billionaire Shadow League Funding American Tennis

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 https://theathletic.onelink.me/eNRy/ptfo • Previously on PTFO: David Foster Wallace, Michael Joyce and the Psychology of Tennis https://pod.link/1685093486/episode/OTUzMmJhNzQtODRkZC0xMWYwLWFjNDUtYmI1NTkyY2VlMmQ2 Hosted on Acast. See acast.com/privacy https://acast.com/privacy for more information.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Pablo Torre?

  Welcome to Pablo Torre Finds Out. I am Pablo Torre and today we're going to find out what this sound is.

• 0:06Speaker 01

  You can look at someone like Frances Tiafoe making the semifinals of the US Open, winning tournaments, and you can say, "I helped make that happen."

• 0:17Pablo Torre?

  Right after this.

• 0:21Speaker 02

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• 1:15Pablo Torre?

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• 1:58Pablo Torre?

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• 2:23Pablo Torre?

  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.

• 2:32Speaker 01

  And history.

• 2:33Pablo Torre?

  And history.

• 2:34Speaker 01

  Yeah.

• 2:35Pablo Torre?

  But even like the US Open this year, which have you been going to?

• 2:38Speaker 01

  Every day, every night.

• 2:40Pablo Torre?

  Of course. How many has it been? Matthew Vorderman, and thank you for being here again, by the way.

• 2:44Speaker 01

  Thanks for having me. How many has it been? I started going to the, what is now called the Billie Jean King National Tennis Center when I was nine years old. Opened in 1978. Old Louis 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.

• 3:09Pablo Torre?

  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 has this character. The audience feels participatory in ways that are not Wimbledon or French Open.

• 3:30Speaker 01

  Yes, 100%. The US Open is 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 USTA, national governing body of tennis in America. They're all about accessibility supposedly. But this US Open has tested their definition of accessibility in ways that I think a lot of people didn't anticipate.

• 4:13Pablo Torre?

  It is hard to get a grounds pass. There is a level now of out of control pricing when it comes to something that is meant for broad, popular consumption.

• 4:24Speaker 01

  Yeah. I would say this year, what has really struck me about the US Open is that I feel like I am in an airport. You can very easily see that in an airport, there is part of the airport for wealthy people who don't wait in lines.

• 4:43Pablo Torre?

  Oh, no.

• 4:43Speaker 01

  Hang out.

• 4:44Pablo Torre?

  Club, baby.

• 4:44Speaker 01

  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 the, 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 Arthur Ashe 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 like this nonprofit organization, which is holding

• 5:28Speaker 01

  its signature in 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 US Open. They're having all the fun and everyone else is just sort of like fighting over the scraps.

• 5:53Pablo Torre?

  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.

• 6:18Pablo Torre?

  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.

• 6:40Speaker 01

  These are people who are playing, who are trying to get to the major leagues of tennis.

• 6:44Pablo Torre?

  Yes.

• 6:45Speaker 01

  There are rankings points on the line, not that many. There is some money on the line, not that much.

• 6:52Pablo Torre?

  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 Jassika on one side, the recently retired Jack Sock on the other, all of these guys still in their late twenties or early thirties. But the fourth player, Jack Sock's partner, a gentleman dressed in all white, is named Bill Ackman. And Bill Ackman has never played professional tennis before.

• 7:28Speaker 01

  In terms of his competitive tennis experience, I think it's safe to say that pretty much ended at Horace Greeley High School in Westchester County in New York. He did not play college tennis. He was a rower at Harvard.

• 7:46Pablo Torre?

  He's hitting the ball right into the net.

• 7:49Speaker 01

  Errors happen in tennis. Even the best players hit a lot of balls into the net.

• 7:53Pablo Torre?

  Yeah.

• 7:54Speaker 01

  But I think there's like a lack of familiarity.

• 7:57Pablo Torre?

  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.

• 8:09Pablo Torre?

  And then you get to his serve.

• 8:15Speaker 01

  I can tell you, it's not a serve that really belongs on the court in a professional tournament.

• 8:22Pablo Torre?

  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.

• 8:39Speaker 04

  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 Ondami's elected, but I'm positive on the country. You know, 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 my 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.

• 9:20Pablo Torre?

  I follow him. I regret to inform my audience.

• 9:23Speaker 01

  He's, you know, sounds off on all sorts of public policy.

• 9:27Pablo Torre?

  The master of the 5,000-word tweet is Bill Ackman. This guy.

• 9:36Pablo Torre?

  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 Roddick on his podcast.

• 9:58Speaker 05

  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 the match where it looked like four players were in the bag. It was a disaster.

• 10:17Pablo Torre?

  And Martina Navratilova, no less than Martina, posted on Bill Ackman's favorite platform, X, quote, "Apparently you can buy yourself a wild card, oh, to have that confidence", end quote. But immediately, the tournament organizers said, "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 "wild card spot", quote, "to bring further excitement to this year's tournament."

• 10:51Speaker 01

  Well, there was excitement about it.

• 10:53Pablo Torre?

  Guilty as charged, I was excited. I remain excited by the fact that this ever [bleep] happened. It's crazy to me.

• 11:01Speaker 01

  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 doubles wild card into the US Open

• 11:17Pablo Torre?

  Yes.

• 11:18Speaker 01

  this year. Usually, these people have some resume of accomplishments in the sport, and that's not what happened here.

• 11:28Pablo Torre?

  And that's why we're doing this episode, is because I've been laughing 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 1:30 PM sun with a shot clock, parentheses, 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...

• 12:13Pablo Torre?

  I mean, kid gloves is not even an appropriate descriptor of how soft, how pillowy these serves were at times.

• 12:23Speaker 01

  Well, tennis actually has a word, has a phrase, that encapsulates this. It's called customer tennis.

• 12:30Pablo Torre?

  That's so good.

• 12:31Speaker 01

  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, you know, beneficial for you not to make them feel bad or uncomfortable.

• 12:51Pablo Torre?

  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

• 13:31Pablo Torre?

  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 shame.

• 13:52Speaker 01

  Yeah, it looked like a quid pro quo happening

• 13:55Pablo Torre?

  No.

• 13:56Speaker 01

  during an actual, during an actual event. That sparked a bit of outrage and crossed the line.

• 14:02Pablo Torre?

  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.

• 14:18Speaker 01

  Yeah, he has been a huge benefactor. He's given millions of dollars to the Junior Tennis Champions Center, otherwise known as the JTCC, in Washington, DC, which produced players like Frances Tiafoe 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 of the USTA Foundation.

• 14:41Pablo Torre?

  He went so far as to bankroll the Professional Tennis Players Association.

• 14:46Speaker 01

  Yes, Novak Djokovic, six years ago, was launching a player group that was supposed to sort of be a ballast against the control by management, the ATP.

• 14:57Pablo Torre?

  It's like a union.

• 14:59Speaker 01

  It's basically a union, and then also with a for-profit entity.

• 15:04Pablo Torre?

  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.

• 15:22Speaker 01

  Every time I turn my head, there's, I feel like there is Ackman involvement.

• 15:28Pablo Torre?

  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 D1 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.

• 16:00Speaker 01

  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 institutionalized, so that this was not so crazy to some of the people who were involved in the decision-making.

• 16:30Pablo Torre?

  The part about this, to me, that I didn't quite realize until we started talking, is that there are more Bill Ackmans. 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.

• 17:09Speaker 01

  And in ways that you didn't ever realize either. I think people are used to the idea that tennis is a wealthy person's 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 US Open, paying tens of thousands of dollars for those tickets, guys who are playing on the courts

• 17:53Speaker 01

  that they are watching, sometimes within months, sometimes within a year or two, are on the other side of the net from them.

• 18:17Pablo Torre?

  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 Athletic's 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. This message is brought to you by Apple Card. With Apple Card, you earn unlimited daily cash back on everyday purchases, like groceries, or merch, or tickets to the game.

• 19:02Pablo Torre?

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• 19:25Speaker 03

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• 20:25Pablo Torre?

  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 are watching tennis now on television. But it's happening like 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...

• 21:01Speaker 01

  Jeff Appel.

• 21:02Pablo Torre?

  Otherwise known as...

• 21:04Speaker 01

  The mayor of New York tennis.

• 21:07Pablo Torre?

  AKA, the guy responsible for why Bill Ackman is somebody that I've been thinking about for the last year.

• 21:15Speaker 07

  My name is Jeff Appel. Thank you for having me today. I started playing competitively since I was about nine or 10 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...

• 21:34Pablo Torre?

  What is Jeff Appel's day job, Matt?

• 21:37Speaker 01

  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.

• 21:49Pablo Torre?

  He's the guy whose bio, when you find it, lists that he is advising these SPACs and arranged an $800 million merger. And yeah, is, 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 tennis.

• 22:07Speaker 01

  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 played professional tennis. And there's this intermingling of quality club players, but also actual former pros.

• 22:35Pablo Torre?

  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 Kleigerman.

• 22:50Speaker 07

  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...

• 23:05Pablo Torre?

  So his skill, it seems to me, is that he is an expert matchmaker.

• 23:11Speaker 01

  He is the matchmaker that is bringing together Wall Street titans and terrific tennis players who may one day become Wall Street titans.

• 23:21Pablo Torre?

  Which brings us now to something called the Finance Cup.

• 23:27Speaker 07

  Excellence, determination, and work ethic. All key elements required to excel in finance and tennis.

• 23:39Speaker 07

  And the two fields join together yet again for the 2023 Finance Cup, as the action starts now at the Miami Beach Tennis Center.

• 23:50Speaker 01

  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 Ryder Cup of tennis. The US versus Europe. Your best bankers and former pros against our best bankers and former pros.

• 24:16Pablo Torre?

  I am so perversely interested in what this is like.

• 24:20Speaker 01

  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 were right out of college or shortly thereafter, have gone on to run like major, major Wall Street institutions and hedge funds.

• 24:41Pablo Torre?

  As they alternate locations between the US 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?

• 24:52Speaker 01

  Yeah, it's a pretty nice trophy.

• 24:54Pablo Torre?

  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 like almost mythological creature that speaks directly to, yes, the providence 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.

• 25:26Speaker 04

  10 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 from '59, 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 over the world come to this spectacular city. Newport is amazing. Who thinks Newport's amazing?

• 25:50Speaker 01

  Now it's all coming together now, isn't it?

• 25:52Pablo Torre?

  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.

• 26:05Speaker 01

  That's tennis, isn't it?

• 26:08Speaker 01

  This is what makes this sport different from all other sports, I would argue.

• 26:12Pablo Torre?

  How would you describe, actually, if you were to sort of give us a taxonomy of wealth and sports, what does strike you as like texturally distinct to tennis as a matter of how they are moneyed?

• 26:25Speaker 01

  I would say it's the participatory aspect of it.

• 26:29Pablo Torre?

  What do you mean?

• 26:30Speaker 01

  In tennis, I think what happens because it's one-on-one, it's because you need a partner.

• 26:36Pablo Torre?

  Hmm.

• 26:37Speaker 01

  There's a situation where the illusion can get created that like, I'm actually playing with this guy.

• 26:43Pablo Torre?

  We're a team.

• 26:44Speaker 01

  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.

• 27:04Pablo Torre?

  Well, in the Finance Cup, to that point, one of the regulations that governs who can participate is that you gotta work full-time in finance, which is to say that all of these elite players that you've referenced are all finance guys now.

• 27:21Speaker 01

  Yeah, yeah.

• 27:23Pablo Torre?

  They are actually on these teams in a corporate sense.

• 27:28Speaker 01

  Yeah, ringers don't exist. You can't rock up there with Patrick McEnroe.

• 27:33Pablo Torre?

  No, you could be a former ATP number three, but you gotta actually earn your corporate sleeveless vest. Your fleece vest. You earn that.

• 27:45Speaker 01

  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 networking in an atmosphere like that.

• 28:05Speaker 07

  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 was 19 years old. He didn't like hanging out with the tennis players. He liked hanging out with business people and just liked business. And went back to school after three knee surgeries. He was at Fortress, now he's starting at Ballyasney in the capital markets.

• 28:42Pablo Torre?

  Jared Donaldson, by the way, the guy who made five grand slams was ranked as high as 48 in the world in 2018.

• 28:48Speaker 01

  Yeah, but not that into it, apparently.

• 28:50Pablo Torre?

  Apparently.

• 28:51Speaker 01

  He always wanted another career. You find that with a lot of tennis players.

• 28:55Speaker 07

  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 so forth.

• 29:22Pablo Torre?

  And the perhaps perfect example of this that I want to focus on with you now is Milos Raonic.

• 29:27Speaker 01

  So how much tennis are you playing now, Milos? Not much. Former Wimbledon finalist, 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.

• 29:48Pablo Torre?

  And now, he's taking the money out of someone else's because he works at Goldman Sachs.

• 29:54Speaker 07

  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 focused 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 closer to that path.

• 30:20Pablo Torre?

  And he isn't alone, it turns out. Just last week at the US Open, former world number six Gail Monfils foreshadowed his own life after retirement. So far, to be honest, I have a new chapter coming the next year. I will work in finance. You know, I already signed to be, to work in the wealth management in the 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?

• 31:01Speaker 01

  Tennis is not easy, you know?

• 31:03Pablo Torre?

  Right, right.

• 31:04Speaker 01

  Tennis is a grind.

• 31:06Pablo Torre?

  Tennis has always sort of reminded me of like boxing.

• 31:08Speaker 07

  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 and getting up again and trying again.

• 31:28Speaker 01

  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.

• 31:45Speaker 07

  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 100, 342, there's a lot of like, hey, we think we, 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?

• 32:18Speaker 01

  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.

• 32:33Pablo Torre?

  Like a mascot, glad hand.

• 32:33Speaker 01

  Yeah. Those jobs don't really exist anymore. And I think Mello should be the first one to tell you that because he had a lot of doors closed. He had all those meetings, but he only got one job.

• 32:45Pablo Torre?

  I like that he remembers that he had 342 of them.

• 32:49Speaker 01

  Yeah, not 346.

• 32:51Pablo Torre?

  That's kind of like how every wide receiver knows how many players were drafted ahead of him.

• 32:56Speaker 01

  Yeah, right. He's hanging on to like how hard it took to get to the finals of Wimbledon in 2016. He's got the receipts for it.

• 33:05Pablo Torre?

  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.

• 33:20Speaker 01

  In some ways, yeah, because they are solicited 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 gets solicited at times and say, can you help out this kid? It happened to Coco Goff when the USTA 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 Frances Tiafoe's and Robin

• 34:05Speaker 01

  Montgomery, too.

• 34:06Pablo Torre?

  It's so funny that even just the way you put it, though, being an early stage investor in Frances Tiafoe is almost literally investing.

• 34:14Speaker 01

  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 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 Frances Tiafoe making the semifinals of the US Open, winning tournaments, and you can say, I helped make that happen. Bill's 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 is unbelievable. He gave me, I mean, he he's done so much for me. I mean, he gave me a chance to play around, around the world

• 34:58Speaker 01

  and not worry about any, 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, he sends her a note of support.

• 35:19Pablo Torre?

  Benefactors.

• 35:20Speaker 01

  Yeah, you're a benefactor. It makes it, you know, and, 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.

• 35:32Pablo Torre?

  And in this case, what you're saying is that Ackman, he is generous in real ways and in exchange he gets to hang.

• 35:43Speaker 01

  It's one of those, both things can be true, as I think is often true with any kind of philanthropy, you know?

• 35:50Pablo Torre?

  Yes, yes, yes.

• 35:51Speaker 01

  It makes us feel good about ourselves, you know? We get something out of it. Humans get something out of being charitable.

• 35:58Pablo Torre?

  It's the Curb Your 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 Koch Estate, speaking of the complications of philanthropy, here we're talking, though, about hosts, hosts of actual tennis matches on their properties.

• 36:31Speaker 01

  Yeah, practice tennis matches in the case of, you know, the Koch Estate where I've been to interview players and watch some practice matches.

• 36:43Pablo Torre?

  What's that house like?

• 36:44Speaker 01

  Henry Moore sculptures, Giacometti sculptures. I mean, really, just, you know, one of the grand properties in Southampton. This is one of the things that happens like the week before the US Open on the highest level where, you know, you can go out there and, you know, Yannick Sinner's staying in Bridgehampton and Tommy Paul's 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.

• 37:21Pablo Torre?

  You're saying that all billionaire tennis courts are created equal?

• 37:23Speaker 01

  Not all billionaire tennis courts are created equal. One of the advantages of the Koch Estate 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.

• 37:47Pablo Torre?

  I am looking at photos of the Koch Estate and they got room for all sorts of things.

• 37:55Speaker 01

  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.

• 38:08Pablo Torre?

  Yes.

• 38:08Speaker 01

  Julie Koch is right up there. Also, one of the things that the JTC 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 US 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. And she grew up in Washington DC in a one bedroom apartment with her mother and her grandmother. And she told me of going up to the Hamptons for a weekend to meet some of these people

• 38:50Speaker 01

  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 being like, thinking like, why are these driveways so long? I mean, it was a completely different world of anything she had seen. Frances Tiafoe was one of the kids who made that trip. He told me, he just described it as just a complete eye opener. He had never seen or kind of imagined houses like that. And to be on their properties

• 39:28Speaker 01

  was, you know, a crazy experience for him, in his words. And he met Ackman and changed his life.

• 39:38Pablo Torre?

  It's hard 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.

• 39:59Speaker 01

  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.

• 40:10Pablo Torre?

  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.

• 40:20Speaker 01

  Yeah, it's a big reason.

• 40:31Speaker 01

  This episode is brought to you by Onin. You know those days where it's back to back meetings?

• 40:36Pablo Torre?

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• 41:20Pablo Torre?

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• 41:51Speaker 03

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• 42:15Speaker 06

  State Fair food is getting smaller and pricier.

• 42:18Speaker 01

  We'll have room for fried cookies.

• 42:20Speaker 06

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• 42:53Pablo Torre?

  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.

• 43:09Speaker 01

  Yeah, I mean, to be clear, he's a pretty good tennis player by all accounts. His favorite partner is a guy named Richie Rennenberg. Richie Rennenberg spent 13 years on the professional tennis tour from 1987 to 2000. Former pro, US Open doubles champ, good player. There is a version of Richie Rennenberg that Bill Ackman can legitimately hang with on a tennis court, especially if he's his partner. Bill's a very good player. He's very good technique. I would say that he likes the faster courts, you know? So the grass court 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-Am's.

• 43:54Speaker 01

  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 were his serve is very good, his net game is exceptionally good, he covers a lot of court, he's a big guy. And his ground stuff's like all of us, you know? He can, days where he's hitting really well, he returns, and days where he's not. But then I asked people like Milos Raonic, 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?

• 44:35Speaker 01

  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 event. 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 Rennenberg, 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 Rennenberg'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 know, you're not hitting heavy top and throwing him up against the fence.

• 45:20Speaker 01

  You're not doing that, but... So, you know, 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.

• 45:33Pablo Torre?

  And so, do the people in Bill Ackman's life, were they supportive of the experiment? Did they want him to do this?

• 45:40Speaker 01

  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...

• 45:56Speaker 01

  I said, why? Did you want him to see, you know, what the actual level was like?

• 45:59Pablo Torre?

  He wanted Bill Ackman to find out.

• 46:00Speaker 01

  Yeah, and he just had a big, big smile. So he was good with it for his own reasons. And even his buddy Richie Rennenberg, 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, when we ask him about Ackman's skill. I remember not long after I got there, his, Bill's coaches, Georgie and Olivier, come over and say, Bill, they just gave Bill a wild card into the Challenger. And I'm like, what? I actually thought, that's kind of cool. I mean, I'm, you know, he's been talking about maybe getting a wild card, a little challenger here, a challenger there. So we started talking about partners and people that 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, you need some, you need somebody.

• 46:44Speaker 01

  If we, 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.

• 46:51Pablo Torre?

  So just to translate that, though, Richie Rennenberg, literal 1992 US Open doubles champion, is like, I am not good enough to help you stay on this court?

• 47:03Speaker 01

  In a minor league tennis match?

• 47:05Pablo Torre?

  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 80p 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.

• 47:38Speaker 01

  So we know what ultimately happened.

• 47:41Pablo Torre?

  Yes.

• 47:41Speaker 01

  And I think like one of the big questions hanging out there is like, would you ever do it again?

• 47:48Pablo Torre?

  That's even on the table?

• 47:50Speaker 01

  What it puts on the table is like, what was the learning experience for you?

• 47:56Pablo Torre?

  What lessons?

• 47:57Speaker 01

  What was the lessons you took from these 67 minutes on the tennis court? The thing about tennis, and really all sports, and really in 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 Ackman's greatest strength. It allows him to make bets on things where everyone thinks he's completely crazy.

• 48:30Pablo Torre?

  Right, right.

• 48:31Speaker 01

  Now, Bill didn't want to talk to us for this episode.

• 48:35Pablo Torre?

  Which remains very disappointing.

• 48:37Speaker 01

  Yeah, I always want to talk to people I'm writing about.

• 48:40Pablo Torre?

  Especially, I'd imagine, if that person's stated investing philosophy is, once again, this.

• 48:46Speaker 01

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

• 49:19Speaker 07

  I don't want to speak for Bill, but he's not a man to back down from any challenge.

• 49:24Speaker 01

  If someone had asked you to play that day, would you have played?

• 49:28Speaker 07

  [bleep] yeah.

• 49:29Speaker 01

  Really?

• 49:30Speaker 07

  100%. Unfortunately, I had a tear in my plantar fascia, so I couldn't have played. I've never said no to a challenge on the tennis court.

• 49:39Pablo Torre?

  Even in that answer? It's like, if I hadn't torn my, I'm just like, oh my goodness.

• 49:45Speaker 01

  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?

• 50:02Pablo Torre?

  No!

• 50:03Speaker 01

  No!

• 50:03Pablo Torre?

  Of [bleep] course not!

• 50:05Speaker 01

  No, and you'd be lucky to get out of there alive. I mean, that's, 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

• 50:26Pablo Torre?

  Ego.

• 50:26Speaker 01

  This sport that has this intersection that I think doesn't exist anywhere else.

• 50:34Pablo Torre?

  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.

• 50:48Speaker 01

  Yeah, you probably shouldn't be on the court. It's the complete flaw of the whole 10,000 hours idea.

• 50:55Pablo Torre?

  Yes, yes.

• 50:56Speaker 01

  Which is that, you know, is it nurture or nature? Like, there's a lot of nature involved, you know? There really is. I mean, and you can get to a certain point in 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.

• 51:18Pablo Torre?

  You can fund the sport, you could invest in the prospects, you could enable the entire premise that America is a plausible tennis country.

• 51:27Pablo Torre?

  On your giant mansion. But the thing you can't buy is the actual ability to hang on a court with real professional athletes.

• 51:40Speaker 01

  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.

• 51:54Pablo Torre?

  Yeah.

• 51:55Speaker 01

  You know, what happened on that court in Newport, Rhode Island? Is that person went to do stand-up?

• 52:03Pablo Torre?

  Yes.

• 52:03Speaker 01

  And it didn't go so well.

• 52:06Pablo Torre?

  What I'm here to tell you is that what I found out is that it was [bleep] hilarious.

• 52:20Pablo Torre?

  This has been Pablo Torre Finds Out, a Meadowlark Media production.

• 52:26Pablo Torre?

  And I'll talk to you next time.

• 52:47Speaker 03

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• 53:11Speaker 06

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• 53:53Speaker 06

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