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Inside the Billionaire Shadow League Funding American Tennis

47m 2s

Inside the Billionaire Shadow League Funding American Tennis

The podcast explores the intersection of wealth, philanthropy, and elite tennis, focusing on Bill Ackman’s unorthodox appearance in a professional doubles match at the Hall of Fame Open in Newport. Despite his $11.7 billion fortune and long-standing support for youth tennis development—such as funding players like Francis Tiafo and Robin Montgomery—the match revealed a troubling reality: Ackman’s performance was laughably poor, with weak serves and frequent errors, exposing the phenomenon of "customer tennis," where wealthy patrons play primarily to maintain social or financial connections rather than compete fairly. This incident underscores a deeper structural issue within tennis: a world where access and visibility are increasingly tied to wealth, with elite events like the US Open becoming arenas of financial inequality. The story also highlights the network of connections between finance and tennis, exemplified by figures like Jeff Appell, who organizes elite Sunday matches linking Wall Street professionals with former pros. These relationships, while seemingly beneficial to athletes, raise ethical questions about fairness and authenticity in competition. The narrative ultimately reflects on what is truly valued in sports—skill, resilience, and genuine participation—versus appearances and transactions. It concludes that while money can fund talent pipelines and create access, it cannot buy the ability to compete on equal footing with elite athletes. The episode serves as a critical reflection on how tennis, a sport often seen as egalitarian, is instead shaped by the invisible power of wealth, with players and fans alike navigating a world where financial status determines both access and experience.

Transcription

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English
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 semi-finals of the US 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 and history Yeah, but even like the US open this year which I've been going to every day How many has it been Matthew butterman 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 Billie Jean King National tennis team? 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 is 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 a hundred percent the US open is the only grand slam And it's I would say the 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's slum what 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 supposedly, but this US open has Tested their definition of accessibility in ways that I think a lot of people didn't anticipate 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. 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 on lines hang out club Maybe 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 dollar renovation they're doing on authorized 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 Non-profit organization, which is holding a signature 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 forward to the US open If 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 Sock's 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 horse really 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 in from the net 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 serve 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 dollars 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 got to rethink the bet. I'm negative on New York if on Tommy's elected but I'm positive on the country Um, 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 by 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 Everything our education 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 Roddick 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 the match where it looked like four players were in the bag. It was a disaster And Martina never to lova. 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 and quote But immediately the tournament organizers said no no no Quote in no way did bill by 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. Well, there was excitement about it We can deal to his charge. I was excited. I'm I remain excited by the fact that this ever But it's crazy to be 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 US open. Yes. 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've been laughing at this for a variety of reasons One of them how Bill Ackman defended himself on Twitter when he said in parts Quotes when 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 And 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 one 30 p.m. son with a shot clock, friend of the season, a new experience for me." And 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, how soft, how pillowy these, these serves were at times. Well, tennis actually has a word as a phrase that encapsulates this. It's called customer tennis. 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 I 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 dollar 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 dollars 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 dollars 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, during an actual event. That sparked a bit of outrage and crossed the 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's been a huge benefactor. He's given millions of dollars to the junior tennis champion center, otherwise known as a JTCC in Washington DC, which produced players like Francis Tiafo and Robin Montgomery, both players that he has personally given money to an order to help launch their careers. And he's been a benefactor of 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 a ballast against the control by management, the ATP. It's like a union. It's basically a union. And then also with a for profit entity, a full McGillah that led Bill Ackman, by the way, to say things like, quote, I understood the plight of the player and quote, but the point here is that Bill Ackman loves tennis, funs tennis is all over the sport in ways that someone like you has seen everywhere. Every time he turned my head, there's 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, actually, on 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. 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. The part about this, to me, that I didn't quite realize until we started talking is that there are more Bill Ackman's. 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'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 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 ungame 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're 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 Jeff Powell. Otherwise known as the mayor of New York tennis. AKA the guy responsible for why Bill Akvin is somebody that I've been thinking about for the last year. My name is Jeff Appell. 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 what is Jeff Appell's day job that 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 is advising these backs 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 tennis. No, he's the mayor of New York tennis because every week, sometimes more than every week, he's organizing tennis matches on Randall's 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 Appell to this Sunday morning game to play with him and a player, Kyle Kleegerman. 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 had picked up a racket since high school. We didn't know it. 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 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 2023 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 am 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 are 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? Yes, 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 like 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, we got to look like a real company. It's a special event. There aren't that many opportunities in '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 is 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-type 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 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. 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, though. Yeah. Yeah. They are actually on these teams in a corporate sense. Yeah. Ringer's don't exist. He can't rock up there with Patrick Mackenrow. No, you could be a former ATP number three, but you got to actually earn your corporate sleeveless vest, your fleece vest. You earn that. And Jeff Appell 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. 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 of 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 Valley Asni in the capital markets. Jared Donaldson, by the way, the guy who made five grand slams 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 like tennis players. I think I've done it maybe, you know, 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 than I want to focus on with you now is Milo's round. So how much tennis are you playing now, Milo? 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. 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 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 close to that path. He isn't alone. It turns out. Last week at the U.S. Open, former World Number 6, Gail Monfie, foreshadowed his own life after retirement. So far, to be honest, I have a new chapter coming in the next year, I will work in finance. I already designed to be to work in the worst management in the Swiss company. So my next chapter, looking at more in 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. Tennis is a grind. Tennis has always reminded me of boxing. There's an appreciation for the soft skill of athletes that doesn't necessarily show on a resume, but there's just that intensity that comes with it, the resilience, just also being okay with failure and getting up again and trying again. And in addition to the extent that 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 a hundred three hundred and forty two, there's a lot 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? Somebody. 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 at like a mask show up at dinner and yeah, those jobs don't really exist anymore. I think me let's 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. I like that he remembers that he had 342 of them, yeah, not 346. That's kind of like how every wide receiver does, how many players were drafted ahead of him. 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. And the symbiosis of how these skillsets 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 solicited for help for really promising tennis players who might not have the means to afford was incredibly expensive sport. I mean, tennis, if you're a kid, is going to cost you like $50,000 a year to develop, right? 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? Happened to Coco Gough 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 Tiafo's and Robin Montgomery too. It's a funny, even just so 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 when 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 Francis Tiafo making the semifinals of the U.S. open, winning tournaments, and you can say, I help make that happen. That was a great guy. He's done so well in life and the fact that he wants to give back to young athletes like me. He's done so much for me. 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 Appell, and the Ackman and Robin Montgomery are, as we speak, talking about her progress. When's a match? You send her a notice of support. Yeah. You're a benefactor. 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. 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 Curberry Enthusiasm episode in which Larry David is wondering about being an anonymous donor. He's like, "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. Yes. Practice tennis matches in the case of, you know, the Koch estate where I've been to interview players and watch some practice matches. What's that house like? Kind of remorse sculptures, jocamedi sculptures. I mean, really, just, you know, one of the grand properties in South Hampton. 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, Yannick Sinner staying in Bridge Hampton and Tommy Paul's in South Hampton and it's funny because there's only a handful of courts that have enough room in the back court to be able to accommodate these professional players. I'm saying that all billionaire tennis courts are created. 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. I am looking at photos of the Koch estate and they got a 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 yes, Julie Koch 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 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 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. Francis Tiafo 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 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. But 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. Be clear, he's pretty good tennis player by all accounts. His favorite partner is guy named Richie Rennemberg. Richie Rennemberg 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 Rennemberg 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 a very good technique. I would say that he likes the faster courts, 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 programs, 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 net game is exceptionally good. He covers a lot of court. He's a big guy. And his ground straps like all of us, you know, he can, days where he's hitting really well over turns, and days where he's not. But then I asked people like Milo's round edge who is 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 it, 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 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 Reddenberg, like, who has, you know, for 30 years played with wealthy people. Originally they brought him into the finance world. Ben Brody, who had been a top advisor to Bill Clinton. He was Richie Reddenberg'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 them up against the fence. 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. And so, do the people in Bill Actman'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, you know, what the actual level. He wanted Bill Akman 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 Ranemberg, 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 Akman's skill. I remember that long after I got there, his, Bill's coach is Georgie and Olivier come over and say, Bill, they just gave Bill a walk heart 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 walk in a little challenger here, a challenger here. 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. If we, because we're 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 this is a translate that though. Richie Ranemberg, literal 1992, US 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 a return, of course, to the everything app X because a week before the match with Bill Akman posted on July 2nd, quote, if we win, I am pretty sure I'll 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 US Open and a gold mentally 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 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 black man's greatest strength. It allows him to make bets on things where everyone thinks he's completely crazy. Right. Right. Now, building want to talk to us for this episode which remains very disappointing. Yeah, I always want 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 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 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 within so much and talks to him all the time. And Jeff Paul 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? Yeah. Really? 100%. Unfortunately, I had a tear on my plant of 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 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 no one Ryan fastball? No, no, of course not. No, and you'd be lucky to get out of their life. 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 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, 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 when you're 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, that's 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*** hilarious. This has been Pablo Torre finds out a metal-lark media production. And I'll talk to you next time.

Podcast Summary

Key Points:

  1. The US Open and other tennis tournaments reveal a stark divide between accessible, public events and elite, financially exclusive experiences, where wealth enables participation far beyond the average fan.
  2. Bill Ackman, a billionaire hedge fund manager, entered a professional tennis match at the Hall of Fame Open with no prior experience, resulting in a comically poor performance that exposed the reality of "customer tennis"—a transactional, performative form of play where the experience serves financial or social gain rather than genuine competition.
  3. The incident and broader context highlight how wealth, philanthropy, and networking in elite tennis are deeply intertwined with finance, with figures like Bill Ackman and Jeff Appell facilitating connections between Wall Street executives and top tennis players, creating a hidden "shadow league" where financial and sporting worlds merge.

Summary:

The podcast explores the intersection of wealth, philanthropy, and elite tennis, focusing on Bill Ackman’s unorthodox appearance in a professional doubles match at the Hall of Fame Open in Newport. 7 billion fortune and long-standing support for youth tennis development—such as funding players like Francis Tiafo and Robin Montgomery—the match revealed a troubling reality: Ackman’s performance was laughably poor, with weak serves and frequent errors, exposing the phenomenon of "customer tennis," where wealthy patrons play primarily to maintain social or financial connections rather than compete fairly. This incident underscores a deeper structural issue within tennis: a world where access and visibility are increasingly tied to wealth, with elite events like the US Open becoming arenas of financial inequality.

The story also highlights the network of connections between finance and tennis, exemplified by figures like Jeff Appell, who organizes elite Sunday matches linking Wall Street professionals with former pros. These relationships, while seemingly beneficial to athletes, raise ethical questions about fairness and authenticity in competition. The narrative ultimately reflects on what is truly valued in sports—skill, resilience, and genuine participation—versus appearances and transactions.

It concludes that while money can fund talent pipelines and create access, it cannot buy the ability to compete on equal footing with elite athletes. The episode serves as a critical reflection on how tennis, a sport often seen as egalitarian, is instead shaped by the invisible power of wealth, with players and fans alike navigating a world where financial status determines both access and experience.

FAQs

Customer tennis refers to matches where one player is not competing at a high level but rather plays to maintain a positive experience or avoid discomfort. In the Bill Ackman match, his lack of competitive tennis experience and soft serves made the match appear transactional, with the goal of entertainment rather than competition, highlighting how wealth and influence can shift the dynamics of the game.

Bill Ackman participated to bring excitement and media attention to the tournament, and he was invited by Jeff Appell, a tennis matchmaker who connects Wall Street figures with elite players. The match was also part of a broader pattern of philanthropy and networking where wealth is leveraged to support tennis development.

Wealth creates significant disparities in access, with high-ticket tickets and expensive training costs limiting participation for many. However, wealthy individuals like Bill Ackman fund junior programs, enabling players like Francis Tiafo to succeed, illustrating how financial power shapes the pipeline of talent in American tennis.

The Finance Cup is a networking event where former professionals and finance professionals compete in tennis matches, blending finance and sports. It serves as a platform for career transition, mentorship, and networking, with participants often moving into finance roles after their tennis careers.

The Hall of Fame declined the offer to avoid a perception of impropriety or quid pro quo, which would suggest that access to the tournament was granted in exchange for financial support—a conflict with the integrity of the competition and its public mission.

Jeff Appell acts as a matchmaker, organizing tennis games between elite players and Wall Street professionals. He fosters relationships that blend athletic and financial worlds, helping former players transition into finance and creating a network of mutual support and mentorship.

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