Pablo Torre Finds Out - What the Hell Happened to Phil Mickelson?

Episode Date: November 18, 2025

Why did one of the greatest golfers ever turn on his own legacy to become a culture warrior with a T-rex skull? His definitive chronicler, Alan Shipnuck, re-visits the many scandals of "a master manipulator" — and uncovers a pattern among Trump-era men who just want the juice.• Previously on PTFO: Phil Mickelson, the Pipeline and Trump's (Alleged) 14-Inch Pipe• Order Alan Shipnuck's bestselling book "Phil"• Pre-order Alan Shipnuck's new book "Rory" 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. I shouldn't do this. I know this is dangerous. I know this is a bad move. Everyone told me not to call this guy. I'm dialing the number. Right after this ad.

How many jokes can we make in one podcast? You and Coppulman set the bar pretty high. It's a lot. It's too much. My mom has informed me it is too much for the record here. But I do need to explain Alan Shepnuck. Thank you for joining us. by the way. Delighted to be here. I got to explain why you're the guy I've been thinking about

as I've been dealing with the one and only Phil Mickelson on X, the everything app, in which I have been feeling a bit like you, just a glimmer of what your life might have been like as the foremost expert. Certainly the author of the book on Phil Mickelson entitled Phil, which you published in 2022, but you've become the guy. You're the guy I come to because Do you remember what he called you, by the way, the quote that I'm about to say? Phil's called me many things through the years. But with Phil, it's all projection. You know, every accusation is a confession.

It's a little Trumpian in that regard. The quote from Phil Mickelson on Twitter, November 22nd, 2020, 23, 5.23 p.m. Eastern was, Alan is the worst liar and a pathetic human. You know, it's interesting because Phil said various things about the book that wrote, I corresponded with at least three of his lawyers. I don't know how many he has, but I was in touch with three of them. The courts are available to a guy like Phil Mickelson. If I was, in fact, telling lies, then that would be libeless. He would have had a strong case if everything he believed was true, but it's just not. I just need to catch people up to the

version of Phil that I have encountered on the internet. The brief speed run through all of this, though, is that Hunterbrook Media, my friend Sam Cappellman, did a piece in which he investigated this group chat that Phil Mickelson was an active participant in. And it's all these bros who are really into this one company, Sable Offshore, which happens to be an oil pipeline off of Santa Barbara. Was President Trump going to come and save it over the objections of California Governor Gavin Newsom? All of that is part of the sort of brass tax here. But I quote tweet the original article, I say, what do I get the feeling that this is not the end of this story? And then Phil tweet something back about how, you know, he's ultra careful, that there's nothing to see here,

that, you know, this is, how dare you insinuate wrongdoing, all that stuff. So I respond with an offer to discuss on the show on Pablo Tori finds out. No response to that. What Phil responds after the episode comes out in response to my original request for comment on Twitter was, quote, I've never heard of you and have no idea who you are, but given what I know to be true and what you report, your tabloid, and I'll wait for the right opportunity. Thumbs up emoji. Then I say, you know, hi, Phil, I'm still the same person you replied to last week. I've been trying to fact-check what you meant when you wrote this to a group chat of

Sable offshore investors. Quote, Big Daddy Trump, ready to swing his 14-inch in front of Newsom's face, will drive up any stock. End quote. Thanks, Pablo. No response. And in that back and forth, the thought occurred to me. I need to talk to Alan.

Phil is once in a lifetime character for us in the sports media. He loves to talk. He loves to take up space. He loves the sound of his own voice. It's been said many times. He always has to be the smartest guy in the room. And wasn't there

an Enron documentary that was called the smartest guys in the room. When I was doing the book, Davis Love told me a funny story about Phil. He said, Phil is the only guy out here who likes to play in the proams. We all hate the proams. It's six hours and tedious. But Phil, he'll play with a heart surgeon, pump him for info. And the rest of his life, he thinks he's an authority on heart surgery. And then he'll do it the next week with a dentist and the next week with a pilot. And Phil just loves to pretend he knows everything. And he's undeniably a bright guy, but he's not a smart. as he thinks he is. And that's how he gets himself in these situations.

I want to make clear that when you wrote your book, it wasn't, and this is according to the New York Times, by the way, because I think it sets the stage for like what we're trying to do here, which is actually answer a couple of questions that I have that I want to pose to you. Because your book, according to New York Times, quote, is not a drive-by character assassination. Shipnuck generally admires Mickelson and takes note of his philanthropy, his sunny disposition, his deadpan wit, his many acts of random kindness, and the fact that he's not a sore loser. The question, though, of, like, what happened to Phil Mickelson

and when did it start happening? And who is he really? Those are some of the things that I think requires this trip back in time to when you first encountered him because it is nuanced. It is more interesting than just, here's a guy on Twitter who sucks,

who claims now this allegiance to Donald Trump's Republican Party, There's something else happening that is legitimately super fascinating to me. I mean, Phil voted for Obama. He was kind of the classic California dude, socially liberal, fiscally conservative, whatever that means. You know, his wife, Amy, they tend to be left-leaning and open-minded. And that was always kind of the Mickelsons that we knew. And where did he take this hard right turn?

Is it strictly performative because he's already angling for a pardon for whatever crimes he may or may not have committed? I mean, you can never put anything past Phil. He's a master manipulator. He is always playing, you know, 5D chess, and it blows up on him. He sets himself on fire, but sometimes maybe it works out. We'll see how this whole thing plays out. I mean, I saw you retweeted, Pablo, that now all of a sudden, the Trump administration's like,

yeah, we love offshore oil drilling off the coast of California. Mikulsan made him become a billionaire out of this deal. And he'll be laughing at all of us. But you just never know with this guy. It's just, he's always working an edge, always working in edge. Seated on my immediate left is Hall of Famer Phil Mickelson, who really needs no introduction, so we're going to dispense with one. Phil, thanks for being here.

Happy to do it. It's fun to start the year. So in 2017, I went to the Madison Club, this very exclusive private golf club in Palm Springs area, and Phil had this secret layer up in the clubhouse, and we retreated there and did this very long, in-depth podcast. And I believe it's the only real podcast he's ever done, except for maybe some smaller promotional things around LiveGolf. And he was interested in the medium and he wanted to talk. The fact that your off-season preparation has been compromised a little bit by the spore ternia

surgery. I have a theory that the injury occurred at the Ryder Cup because your balls got so big and heavy, they possibly created some sort of stretching or tearing. I'm not a doctor, but am I on the right track there? Well, it was an umbilical hernia, so it was behind my belly button. What you're referring to is a little bit lower. I do appreciate that. It's probably one of the nicest things you've ever said to me over the years. And I said, why are you not on social media?

You would kill because you're funny, you've got a needle. He said, because of my personality, I'll go in too deep. He's like, once I start, I'll never stop. I have a mind that kind of dives into things all in that we talk about. And I think it's a very positive thing, but it can be a negative thing. I've never tried a recreational drug in my life because I am scared out of my mind that if I were ever try something like that, I could easily dive right down that path and be all in on that. Amy describing to me as obsessive, and I think he is about a lot of things. Do you remember the first time you got quality time with Phil Mickelson, when that was, where that was?

It would have been in 1994. I was an intern at our beloved alma mater Sports Illustrated. And Phil was the first one at that level who really understood how to play the game with the media. Like Jack Nicholas famously knew the name of every reporter. He knew their first name. And when they'd ask a question, he'd be like, he's like, well, Pablo, you know, that's a very insightful question.

Like, Jack was not subtle about it. And, you know, you're sitting in your chair like, oh, Jack liked my question. where, Alan, that move has 100% success rate with us sad reporters who are, like, charmed. Totally. But, like, Phil went to the next level. You know, he started taking guys out for dinner. He would start playing casual rounds of golf.

Like, he really took it to a different level of creating relationships. Now, he came up to me, and he kind of introduced himself. He's like, oh, I hear you're, you know, at Sports Illustrated. And, you know, someone told me you could be the next Rick Riley, which is an amazing thing. Because, you know, Riley was a god back then. Oh, my God. And I was a lowly intern, and, you know, he lays it on thick. And of course, I was like, oh, wow, I didn't even know Phil knew who I was.

And so, like, how many superstars in a sport are going to go up and treat himself to an intern? You know, golf is a little more cloistered incestuous B, but nevertheless, like, that tells you. Let me be clear about this. I have never heard of someone of that stature taking the time to fluff someone of so little stature at the time. Exactly. That was Phil. So then it's easy to forget now with all the bluster and the bullshit, you know, who Phil was. And it was particularly dark time for American golf.

You know, the best players were Corey Pavin and Marco Mira and Tom Lehman. I'm falling asleep remembering those names. Exactly. Very boring, very anodyne, charisma-free. And Phil arrived and he had aura. A good smile. He left to the hole. Good looking.

That put to win the golf tournament. The 20-year-old amateur, Phil Nicholson. You know, he had charisma. He was a star before we even got to the PGA tour. He won a professional tournament while he was still an undergrad at Arizona State. Bill Nicholson. I feel I really played well, but, yeah, the put on 8 was great. Boy, I talked about chills in your spine.

That was them right there. And you had the popped collar, and you had the slick-backer. He's a good-looking guy, and he was the can't-miss kid in golf. He was Tiger Woods before Tiger Woods arrived. And Phil was a larger-than-life character, you know, even early on. He lived big. He got his pilot's license. He drove fast cars.

He had a beautiful wife who was a cheerleader for the Phoenix Suns. And he played the game in this crazy sort of way where he was always living on the edge. He was high risk, high reward. What a putter. What a performance by Nicholson. He would self-immolate occasionally, but he was winning tournaments at a regular clip. And for three or four years, Phil was the golden boy. And then Tiger Woods turned pro and threw into sharp relief all the flaws in Phil's game and lifestyle.

You know, Tiger never respected Phil because he recognized this was an awesome physical talent. He was not really maximizing what he'd been given. And in Tiger's world, that was the ultimate sin. Look, the whole thing of you getting access to Phil at the house, you getting access through this relationship that you're building with his wife, Amy, who was essentially, by the way, like his flack, his, like, PR rep, the person handling, like, his public image in lots of different ways. But it reminds me of, like, Phil at his most fun.

You know, for people who don't remember what that was like, What was the part that was legitimately charming, that you were like, this is a blast to be in this guy's orbit? Yeah, I mean, he's a performer. On the golf course, in the press tent, you know, on the rope line signing autographs. He just, he loves the spotlight. And so his pre-tournament press conferences were electric

because you never know what he'd say. Can he tell some a little bit about the name of Mickinson and whether there was any Scottish heritage to that? I don't know. I don't know. maybe a wee bit. He wasn't that careful. And again, this is all in,

you can't talk about Phil without talking about Tiger. And your Tiger is the ultimate soulless kind of corporate warrior. And, you know, he's got dead eyes. And his mouse moving, but he's not really saying anything. And Phil had come in. He was freewheeling and fun. And he's giving reporters shit. And then it was just the way they played the game.

Now, obviously Tigers was at the most exacting tournaments on the harshest setups, Tiger's Way was clearly superior. That's why he won all those major championships, and it took Phil a long time to figure out the formula. But week to week, Phil was just more fun in every way. It's more fun to watch, more fun to interview, more fun to watch them interact with fans. He was just a performer, and he made the golf beat quite lively for everybody.

Yeah, I'm reminded of a part of your book where you're in now, I think it's 1999, and you have this encounter, with Phil. What was that story? The golf beats is unusual because like if you're the NFL writer for Sports Illustrated, you might not see the same team twice in the season until the playoffs. You know, you're bouncing around. Golf is just the same people week after week. You know, I call it high school with private jet money. And it's this very incestuous world. And so there was always this chumminess between the reporters and the players because you just had to see each other every week.

And when I came out, you know, at Sports Illustrated, we did things a little differently. And like my mandate was like to cover golf like the other sports. And so I would say some of my coverage had a slightly harder edge or was more sardonic or whatever. And that graded on Phil. And again, now we're into this era where, you know, Tiger is the man. And Phil has been very quickly relegated from the headliner to the undercard.

And I was doing a mailbag back then. You know, this was the 90s, so it was a little ahead of its time. And there were a lot of jokes about Phil's weight back then. And I do remember one reader wrote in. And, you know, I didn't publish it. So it's sort of on me. But the guys like, oh, I hear the Mickelsons are pregnant. You know, which one?

Phil or Amy. You know, it was stuff like that. It was a little sophomore. So my bad. But that wasn't, those weren't my words, but it was in my mailbag. So it was stuff like that he was upset about. So Phil pulls me into the under the grandstand at Medina Country Club, which is this very regal setting in golf, by the way. And it's Sunday the PGA championship.

Tiger's going to win. There's a great feeling in the air. You know, this is Tiger's first major. He really will have won since the Apoccal 97 Masters. And it's all anyone can think about. Phil's mad at me about some random line in a mailbag from six months earlier. Like, it's just incredible. And yeah, so I mean, he's standing so close to me.

And Phil's a big dude. He's like 6'3. And, you know, I can smell his breath. It was pungent. And he's like, just throw the first punch. And it's so ridiculous because unlike Phil, who's, you know, was going to finish 80 second or something. Like, I still had to work. I had to write a cover story about Tiger Woods winning the PGA championship.

Like, it was just the most idle threat. He knows I'm not going to throw the first punch. I know he's not going to throw the first punch. I know he's not going to throw the first punch because he's this guy who has a reputation of protect. So the semantics of it were ridiculous. Like, he should have just said, I think you're a dick. That would have been more to the point. But just throw the first punch.

Like, come on. So then we go back and forth. And we have a philosophical discussion about the role of the media. But he says something that's really interesting at the end. And he said, you think you know me, but you don't. And it was like, you know, he had a little Clint Eastwood squint. And there was a little bit almost of a dare is how it came to germinate in my brain. And as I got into the reporting of the book, I realized, yeah, I thought I did know him, but I really don't.

He wasn't wrong. I mean, just so many contradictions and so many shadows and so many skeletons and so many secrets. And as public a life as he's led and the way he's chewed the scenery, there's so much of people that know. And that's why we're doing this podcast, Pablo. Like, there's a whole world in that sentence. I'm always like wary of like, okay, are we psychoanalyzing somebody? But two things are true here. He spoke to like hundreds of people for your book.

And also Phil Mickelson himself, a psychology major. Yeah. I mean, that's like, you know, his wife gave me famously beautiful. And talking about their romance, Phil tells me like... The physiological response of the human body for fear is the same as it is for arousal. So when you're afraid, your heart pumps faster and your lungs expand and your nostrils flare and your senses become much more acute. And that's what happens when you're aroused, you know. So what I would do is I would, I would take Amy or, you know, to a suspenseful movie, not a horror movie, but a suspenseful movie.

And during this suspenseful time, I would grab their hand and I would kind of rub it, you know, during this, And she would displace her fear as arousal or attraction for me. And that's how I was able to, you know, when I didn't have as much to work with, was able to land such a gem. I just want to reiterate, quote, she would displace her fear as arousal or attraction for me. I'm just like... It sounds so romantic.

But there is, but there is the whole, like, the through line that you're, identifying is the dude is up to something. Everything about Phil is just funny. I mean, until it's not. Like, like, and then he's, it's gotten, he's gotten edgier and he's gotten more polarizing. And it's turned in, it's kind of turned a little bit. But for most of his life, it was just, it was just, you had to roll your eyes and laugh.

I mean, look, the whole thing of how much money has Phil made, like the, the large ass of being, what was it, the second highest, earner on the tour for a long, which is like effectively how so how much money has Phil earned when you just talk about what he made off of golf and like marketing on the books? Oh yeah. I mean, he was making almost $100 million a year. Like Tiger was at 120. Phil was like in the 80s or 90s. Like he had blue chip sponsorship deals and he had a bunch of them. And part of it was because like these financial services company, which is also hilarious, Phil's always been sponsored by financial services companies.

But they'd pay him $10 million a year and he'd wear the logo and that's cool. But what they were really buying was his time because Phil would come in for these outings with the most important investors and clients. He would request a binder and he would study it. So let's say it's, you know, KPMG or Bearing Point or whatever the company was,

they were bringing in 40 dudes for a pro-am. Phil would get a dossier on all 40, and he'd memorize it. So he'd meet this guy, and he'd like, hey, oh, hey, Jim, I heard you won your club championship. Congratulations. And like, hey, Bob, I heard your daughter got a scholarship to Stanford to play volleyball. I was so proud. And people were so dazzled by Phil.

And no one else would make that kind of effort. And that's part of why he was valuable. And it was partly just his stick. Like, he loved that reaction. And so Phil had all these huge deals. So he's probably earned easily a billion dollars. Now, you may remember Phil had this big public dust up where he complained about the tax rate in California.

And Phil Mickelson making some noise. He's hosting a big golf term this week saying that he's going to have to make some drastic changes because of what's gone on in terms of taxes in California. This is one of his many little scandals. And this is going back 20 years. The four-time major champ who rakes in nearly 50 million a year says he's not yet sure. if he'll leave California for a less taxing state. He also apologized for offending anyone.

I think that it was insensitive to talk about publicly to those people who are not able to find a job that are struggling paycheck to paycheck. This is a funny story. So he complains on national TV about how much has to pay in taxes. No one's making him live in California. Most of his brethren have moved to Florida, Arizona.

He's chosen to be in California because he's from California. And we, you know, he likes it. the weather, he likes the lifestyle, like, sure, like, it's a choice, Phil. Then before his next tournament, and he's going to go in and have to face the music and do a press conference, they're out in the parking lot, and there's his PR guy, and there's a tour staffer, and they're kind of strategizing. And the tour staffer says to Phil, listen, Phil, nobody wants to hear, you know, a guy who's making $40 million, complain about their taxes, and Phil's like, it's 50.

I mean, that's not really the point of this conversation. We're trying to get your ass out of trouble here, Phil. But even then, he can't, he's just, Amy used a word once to describe her husband, that he's a rascal. And it's a great word. It's always stuck with me. He just can't control himself. And so Phil had, he made a hell of a lot of money, but he had a very high burden rate from the mansions, from the G5, from, you know, Amy, she liked to

buy a nice gift. She bought, Phil, a T. Rex skull for a birthday present. I don't know how much a T. rex skull costs. Well, you can't get that at Macy's, right? Like, you know, she bought him a meteor that was like, like, you know, weighed like a thousand pounds. Anytime your gifts end up sounding like things in a supervillain's layer, you're like, I think you might have too much money. Yeah. So, Phil made a lot, but even just the, the, the obvious trappings of, you know, conspicuous consumption, like he had a high burn rate. Then you get in a lot. Then you get in a lot. the gambling. And that's where, you know, it was going out the door really fast. The accounting, by way, just to recap it briefly, like what Billy Walters says, you know,

citing his two very reliable sources and the betting records that form the foundation of this part of his book, you know, we're talking about losses of approximately $100 million, according to Walters, while betting more than a billion over the last 30 years. And so whatever the truth is inside of this triangulation of just estimates, It is, as far as I can tell, the most a pro athlete has ever wagered on sports over the course of a career. You know, Phil lost a lot of fans over how he treated his caddy, Jim McKay, famously known as Bones. And this all came out in my book. It had never really been reported before that he owed Bones about $900,000 through the years.

And when the FedEx Cup was first introduced, this big season-ending Bonanza bonus program, you know, a lot of it was deferred. the first year, the guy who ever won $10 million, like $9 million of it went to his retirement count. And so how do you pay your caddy off of that? And then the deferred compensation went away, but it was still, it was like this new thing that every player and caddy had to kind of account for because it wasn't really traditional earnings. It's a bonus. The caddy deserves some, how much, whatever. So this was not an unusual negotiation. And so Phil and Bones kind of talked it out, but like Phil never paid. It just kind of started accumulating. And so $900,000 is a lot of money to anybody.

It's especially a lot to a caddy. But they were having success. They were winning. Bones was, he didn't want to rock the boat. He was just kind of waiting for Phil to make him whole. And finally, eventually, when they decide to part ways, Phil sends him two checks. And it totals 800,000, not 900. Like, even so, it just like, it's like his little, fuck you.

Like, I'm just going to hang on to a little bit. Just, you know, and there wasn't a written contract. It's not like Bones is going to sue him in a court of law. So he just had to swallow it. But why didn't Phil pay him? Was he really in such a cash crunch? He just couldn't pay bones the money? I mean, it seems fantastical, given how much he was making.

But Phil Migglinson made a fortune. How much of it did he hold on to? That is the enduring question. Right, which then informs the potential motives for why is he always trying to swing for the fences financially. Is that, again, and I think there are multiple through lines here. A, he always does this with everything, so there's just that consistency. And then there's also just the, well, maybe he also needs it more than we realize. How much of that drive his behavior to go to Live Golf and get that $200 million payday,

although it was a little less than $200. He got a haircut after my book came out. But we got to talk about Live Golf because it's so fundamental to Phil. And the very short version is that Phil for decades had the... these gripes with the PGA tour. And he was always, whether it was Tim Fincham or Jay Monaghan, the two commissioners, he was always going to them with these big ideas, how to blow up the tour, how to change it, how to improve it.

And they'd sort of pat him on the head and send him on his way. And when Liv Golf was percolating, that gave Phil the leverage he always wanted. And so that's what he famously told me. Why am I negotiating with these scary motherfuckers? Because this is a once-in-a-lifetime opportunity to reshape how the PGA tour does. its business. In a piece posted on the Fire Pit Collective, the World Golf Hall of Famer, told journalist Alan Shipnuck, the author of an upcoming unauthorized biography of Mickelson, that he would support the new league, even though the Saudis are scary to get involved with.

We know they killed Koshoggi and have a horrible record on human rights. They execute people over there for being gay. Knowing this, why would I even consider it? Because this is a once-in-a-lifetime opportunity to reshape how the PGA tour operates. I'm not sure I even want it to. succeed, but just the idea of it is allowing us to get things done with the PGA tour. Phil was working both sides of the street. He was trying to make all these structural changes of the PGA tour in case he stayed. He basically helped write the constitution of Live Golf in case that launched. The predecessor to Live Golf was something called the Premier Golf League. Phil was involved with those guys. Phil also went to, you know, these private equity dudes

and tried to steal all the IP and just create his own Live Golf. Like, he was working four sides the street, more or less simultaneously. It's interesting how it might or might have played out if you never picked up the phone and called me and told me the things he did. What I didn't fully appreciate until you're articulating it now, I think, is the reason this guy who always has an angle was calling you, the guy famously working on this biography

that was unauthorized, that was collecting hundreds of testimonies of all these people around him. The reason he was calling you, was what? What was his actual game there? So, yeah, I mean, I went to Phil face-to-face, asked him to do sit-down interviews for the book three times. He said no.

But he knew the deadline, and he called me a week for the deadline, because in the end, and this is my speculation, but very informed in speculation, is that he just couldn't stand the idea that I was going to write about this chapter of his life and a professional golf and not fully appreciate how smart he was. And that he had outsmarted the Saudis, he had outsmarted the PGA tour,

and that he had finessed this entire situation. And I had to understand that and give him the credit that he desperately needed. That's it. That's the only reason. Because his lawyers told him not to call me. His agent told him not to call me. And he kind of white-knuckled his way all the way through the process until I was about to hit said. He's like, no, I got to tell him.

I just, I got to tell him. And it's unbelievable. And he could have called any other reporter and still kind of put his story out there. And he could have tried to get, you know, his flowers a different way. He could have called, he could have called actual Rick Riley. Yeah. Yeah. He had 20 reporters in his phone. He could have called me.

It's just, it's truly unbelievable. It's a whole pattern of how he's lived his life. And it's like, you know, it's how he's gotten himself into two insider trading. scandals. Like, there's a lot of easy ways to make money. When you're sitting on a lot of money, you can make more money pretty easily, right? Put in the bond market, whatever. You can buy Apple stock. It's not that hard, but it's more fun if you're Phil to, like, get a little tip and feel like you're getting over on everybody else. Like, I honestly believe that's what is. I'm not even sure it's about the money. It's just the adrenaline. It's just, you know,

there's a good quote from Stuart Singh, who's a contemporary of Phil's. And he says, you know, fills the ultimate juice guy. He just needs juice and everything he does. The practice round wagers, the crazy shot selection during the tournament. And, you know, Sink said, where does math meet juice?

Vegas. That's why I feel so into gambling. It's just, I mean, of course the money's part is like, that's part of the drug, but it's really about the juice. And I think that's what it comes down to in these deals. It's, you know, it's just the juice. And so that was picking up the phone

calling me was the juice. Like, oh, I shouldn't do this. I know this is dangerous. I know this is a bad move. Everyone told me not to call this guy. I'm dialing the number. Oh, my, you know, my heart's racing. Like, I just, it's like, you know, you and I go bungee jumping. Phil does it in other ways. But it's, it's been a pattern for decades. And you don't have to be Sigmund Freudier to figure out what's going on. Like, the first insider trading case was almost a decade ago. And he skated on that one. He refused to testify that could have kept his close friend out of jail, Billy Walters. Phil had to give back a million dollars in quote-unquote ill-gotten gains back to the government, but he ultimately wasn't charged with a crime.

He was just named as a relief defendant, but it definitely could have gone another way for him. But do you need his way out of that? So at that point, I'm probably going to give up the market. Like, I'm probably not going to be in shady group chats. Like, I'm just going to sit on my pile of money and put it somewhere safe. And, but, you know, that's not Phil. He needs the juice. So, oh, you've got some, you got some weird underground oil pipeline.

Yeah, bring it on, baby. Let's go. I want to turn to just his online persona. When did that turn in your view? Like, when did it emerge that, like, wait a minute, hold on. The Phil as this internet character, that has fundamentally changed some. Yeah, so I think he was always in there,

but it was kind of disguised because when we were driving around in his golf cart in Rancho Santa Fe, he made some very, so that was I think 2018, it was way before Live Golf. And he was talking about, okay, we're finally going to leave California.

We're looking at this land in Florida. Like, I'm getting out of this hellhole. That was kind of his thing. And he had some strong things to say, that part of the conversation is off the record, which I always honor, so I can't go into the specifics, but loosely it was about taxes,

some of it was cultural. So I think, I mean, you see this in people as they age, and they can become more conservative. It wasn't so outlandish that I never heard it before, but the persona kind of curdled in the Live golf years. And there's, you know, Liv was this group of renegade,

They were kind of like flying the pirate flag. And they took pride in being iconoclass and being risk takers and kind of breaking up this stodgy sport. Because of that, no one wanted to host golf tournaments in the first year. They were struggling to get venues. Only one person with a portfolio of golf courses really raised their hand and said, I'd love to have you guys. And that was Donald Trump. So right from the beginning, he threw them a lot of.

lifeline and of course he was being paid millions of dollars to host these tournaments that are operated by the public investment fund of Saudi Arabia unprecedented situation for a former president but we know that Trump has a flexible view on these things and so there was this nexus between Trump and live from day one and a lot of the players had felt encumbered while they're on the PGA tour about speaking out on certain things, including social issues, and they'd been discouraged from doing that by their agent, by the tour infrastructure. And live was a much more unbridled atmosphere, shall we say. And especially the first couple of years, like anything goes, the players started speaking more freely about their own political beliefs, their own thoughts on current

events, world events, but they had this close relationship with Trump. And so, They were especially prone to amplifying certain talking points. And so you saw that with Phil right away. I mean, Bryson Deschambo was up on stage on election night when Trump was reelected. Whether there's any left-leaning players on live golf, they certainly haven't voiced that. You know, I think there's been this conformity of thought and there's been this almost pure pressure. Like, if you're going to speak out, like, this is our agenda. I think Phil already had those feelings.

He kind of held them in. Once he got to live golf and he sussed out the political climate, he just let it rip. Well, you know, the people I think of when I watch and unfortunately continue to read his Twitter feed, and I see not just like the Trump favoring that's sucking up, but when I see Phil Nicholson's Twitter account these days, the people I think of on Twitter who remind me of this sort of evolution that I've been able to watch from afar are Aaron Rogers and Elon Musk.

When I just think of like, oh, wait a minute, like these were guys who were once known as very media friendly, left-leaning, actually, known for being interesting, known for having personality, known for being expansive and thoughtful, who were fun. And sometime over the pandemic and certainly in the years since, they became these sort of culture warriors who I think are not just defined by like one. wanting to say the thing that feels unsayable in polite company. They're also sort of defined, in my view at least, as almost projecting this misery.

And now it just seems like every time I read the transcript of a group chat or just what he's tweeting, it just seems like there's a sadness there. And I wonder if you've noticed that too. Oh, yeah. Yeah, it's sort of like a siege mentality. I think for Phil, it really started with the Billy Walters case. because he was in legal jeopardy. He certainly took some hits.

He lost sponsors, all of that. But Billy Walters is a very popular guy in the golf world because he's just fun to be around. He loves to play golf. And Phil and Billy were members at two of the same clubs, which is the Madison Club in Palm Springs and the Rancho Santa Fe Country Club where they both have homes. And people kind of had to take his side. Are you on Billy's side or you're on Phil's side? because you couldn't be on both.

And pretty much the entire world took Billy's side. And Phil became kind of as outcast. And anecdotally, is not really welcome at either of those places that used to be his stomping grounds. You know, Phil's whole life had been this great escape, this great up and down. You know, he did it on the golf course and he did it away from the golf course. He was always able to just finesse it. He was just always able to, you know, just get out of a jam.

That was the first time it really caught up with him, not legally, but in his social world, his reputation in golf, a lot of people turn their back on Phil after that. And then you fast forward to the live golf, that really turned him into a pariah. And so I think that that joyfulness that Phil exuded, that little twinkle in his eye, it just got extinguished. And now he's under siege again. And of course, it's all of his own doing. I'm not saying it's not, I'm not asking for sympathy on behalf of Phil Mickelson,

but I think it explains where he is emotionally. And the Elon Musk parallel is interesting. You know, Elon blames the woke left for, you know, indoctrinating his transgender child. I think that's a big part of Elon's story. I would say there's so much. in Phil's life who has been gender fluid and I think it's caused some pain for him in his as a human, as a person and he's adopted Elon's outlook that it's the woke left's fault.

And so it's a very fascinating parallel between those two characters. Like that's one thing they have in common. And I think it's political. it's personal, it's part of this larger cultural war on the media, it's everything. And I suppose there is something that I find deeply sad but also relatable near the end here as I contemplate, like what is, who is Phil Mickelson, this person that I found myself arguing with on Twitter lately. He's a guy who is living his life online. It just seems like he's a guy whose brain has been consumed by the internet. And I hate to do the legacy of it.

exercise, but I think in this case it's actually instructive. Like, what's different now in 2025 about what you might have written as the guy assigned this particular story? It's just so classic, Phil, for him to say, I don't know who you are. You've been on a generational heater. It would take one quick Google search to figure out who you are. He also just had responded to me a week before. That's the thing.

I'm just like, I get it. Maybe you didn't watch ESPN or whatever between the hours of 5 and 6 p.m. Eastern over the course of the last 13 years. That's totally fine. even though you love sports betting. I'm just wondering, do you just not remember that you replied to me a week ago?

It's just, it's like, it's nonsensical. And this is a funny thing where long after, you know, my book came out, Phil tried to make the bad faith argument that our conversation was off the record, even though I'd requested multiple times to interview him for the book.

And he said to me, I don't want to talk about anything for the book other than Saudi Arabia. And also, I had fact-checked some stuff from our conversation through his lawyer. Obviously, that's going in the book about fact-checking. I think people saw through that as just total BS. But later, subsequently, someone said to him,

this is actually a live tournament in Saudi Arabia. So he goes back, he's called these guys scary motherfuckers. It's the first time he's going to Saudi Arabia. And he's like kissing babies and trying to create all this goodwill and whatever. And then in this press conference, someone says, oh, you know, the interview you did with Alan Shepnick, blah, blah. He said, I will reiterate, I never did an interview. with Alan Shipnick.

I never did an interview with Alan, Shipnik. And mispronounced my last name, you know I've known for 30 years. And someone very close to Phil said, I'm sure he did that on purpose because he was going to be like, oh, well, you know, that's how he's going to game the system,

is that he didn't say Shipnuck, he said Shipnick. And so that's a different person. And it's like, that's a pretty funny name. I don't think there's any dispute about who I am and what we're talking about here. And like, but that's how Phil's brain is. Like, oh, yeah, I can say,

name differently and then I can deny it later. So I think that's kind of like what he was doing with you. I'm going to tweet you. But then it doesn't work out, but now I don't know who you are. Like, so there's just... Just clearly also, he left, again, the obvious safe shot on the board at you, which was ship d'b-hack. How did he not go just that direction?

Well, I mean, you can go back to recess in elementary school. I can give you a whole bunch of variations, but, yeah, you know, he completely whipped. Ship Cuck. Okay. I'm just workshopping now. like, what would I make fun of you with? He's really just missing. It's objectively a great name for put-downs.

But so the Phil legacy, this is one of the bitter ironies in this from Phil's perspective, is he was actually right about a lot of things when you're talking about this whole war for the sole professional golf. Like his two main talking points to me was that the players needed more say in their governance on the PG tour. And you saw that when Jay Monaghan, the country. commissioner sold them all out and created this backroom deal, the Saudis. And ever since then, there was so much outrage, they've blown the whole thing up.

They've given the players more seats on the board. The players now run the PG tour. The commissioner role has been so diminished. Monaghan's retiring and they're not even to have a commissioner anymore. They're going to have a CEO. Like, Phil was right about that. And the other thing was that the players should be compensated more. And, you know, the tour spent $75 million to build this headquarters.

They had hundreds of millions of dollars. in reserves, and then Liv Golf arrives, they turn the spigot on, all of a sudden, the players are getting paid twice and much they used to. Like Phil was right about that too. And so, on the merits, he could be vindicated.

He could be the hero to every professional golfer because he tripled their salaries. He changed the landscape. He let them run the tour themselves. In fact, the tour had to become, it was a 501c3. It was just a charity organization, a past-through organization.

Now it's a for-profit with a billion and a half dollars. of investment. So Phil was was bang on, but no one will ever give him credit because of the way he handled it. He just napalmed the bridges on his way out of town. And so what is his legacy? I mean, he's clearly one of the 12 to 15 greatest golfers of all time. You can't take that away from him. But his inability to win the U.S. Open, six runner-ups. So even as much as he's accomplished, the ones that got away are so memorable, he'll never live. live them down. And now you get into this late period fill over the last decade where he's

being investigated by the SEC and he's become this right-wing internet troll. It's just, it's a mixed legacy. And it's all of his own making. And the craziest thing about all of this is after he won the PJ Championship in 2021, in his 50s, one of the greatest victory laps and the history of the sport, all he had to do was just right off into the sunset. He would have been in the tower of Jim Nance. He would have been a Ryder Cup captain. He would have been honorary star of the masters. He would have made $20 to $50 million a year in perpetuity just doing those things.

All the endorsements, all the pro ams. He had the easiest road in front of him, and he gave it all up because he had to be the smartest guy in the room, and he had to reinvent professional golf in his image. And now he's a pariah. And so it's just an incredible own goal. But in his mind, he was right about everything and it was worth it. And that's the ultimate paradox of Phil Mickelson. There is one more thing he was right about, it turns out.

He was absolutely right about what would happen to him if he logged on to social media. Yes, he was. He called it. He called it, dude. He's a generational reply guy. This has been Pablo Torre finds out a Metal Arc Media production. And I'll talk to you next time.