Michael: A USA Today investigation found that Donald Trump has been involved in over 3,500 lawsuits in his life. Kevin: Hold on, 3,500? That can't be right. Michael: It is. That’s about 50 lawsuits a year, every year, since he was born. And what’s fascinating is that a surprising number of them, and the mindset behind them, start on the golf course. Kevin: On the golf course? I thought that was where deals were made, not where lawsuits were born. Michael: Well, that litigious, win-at-all-costs mentality is the core of the book we're diving into today: Commander in Cheat: How Golf Explains Trump by Rick Reilly. Kevin: Rick Reilly... the name sounds familiar. Isn't he a huge deal in sports writing? Michael: Huge. He's an 11-time National Sportswriter of the Year. He spent decades as the star columnist for Sports Illustrated. When a guy with that kind of access and deep love for the game of golf says someone is the biggest cheater he's ever seen in his fifty years of playing, you tend to listen. The book was polarizing, for obvious reasons, but it's packed with stories from over 100 insiders—caddies, pros, and partners. Kevin: So this isn't just political commentary. This is a sports legend taking a hard look at a public figure through the lens of the game they both love. Michael: Exactly. And Reilly’s argument is simple but profound: to understand Trump, you have to understand his golf game. It all starts with the cheating.

Kevin: Okay, so what kind of cheating are we talking about? Is it just fudging a stroke here or there? I mean, let's be honest, a lot of casual golfers take a mulligan or two. Michael: Oh, we are way beyond a casual mulligan. Reilly documents a level of cheating that's almost performance art. He calls it the "Trump Bump." It’s not just about improving a score; it's about constructing an entirely alternate reality where he is always the winner. Kevin: Alternate reality? That sounds dramatic. Give me an example. Michael: Alright, here’s one from a frequent guest in Trump's foursomes. Trump's ball is off the green, down a hill. The guest is in the fairway, watching. He sees Trump make a full chipping motion... but no ball comes up the hill. Kevin: He whiffed it? Michael: That's what you'd think. But then, Trump walks up the hill, strolls over to the hole, sticks his hand in, and pulls a ball out, triumphantly declaring, "I chipped in!" He called it the "invisible dunk." Kevin: Come on. He just pretended to chip in? He faked a miracle shot? Who does that? Michael: Someone who, according to Reilly, needs to be the best, even in a fantasy of his own creation. But it gets even more audacious. It’s not just about what he does; it’s about what he gets others to do. There's a now-famous story from ESPN's Mike Tirico. He was playing with Trump, Jon Gruden, and Ron Jaworski. Kevin: That’s a serious group. Michael: Right. On a blind par 5, Tirico hits a perfect shot. It's heading straight for the pin. The whole group is excited. They get up to the green, and Tirico's ball is nowhere to be found. They search everywhere. Finally, they find it in a deep bunker, fifty feet left of the hole. A terrible lie. Kevin: Oh, that’s heartbreaking. A perfect shot just vanishes. Michael: Vanishes is the right word. After the round, Tirico is talking to Trump's caddy, and the caddy just comes clean. He says, "The boss didn't like where your ball was, so he picked it up and threw it in the bunker." Kevin: He threw his ball in the bunker? That's not cheating, that's sabotage! It's like something out of a cartoon, where the villain ties the hero to the train tracks. Michael: Exactly! And that’s the core of Reilly’s first point. This isn’t just about shaving a stroke. It's about a fundamental disregard for the rules and for his opponents. Reilly quotes a Harvard psychiatrist in the book who suggests this behavior stems from a deep-seated narcissism. It's not just that he wants to win; it's that he cannot psychologically tolerate not being the best. So, if reality doesn't conform to that need, he'll just... change reality. Kevin: So when he claims to have won 18 club championships, which Reilly debunks pretty thoroughly, it’s not just a lie. It’s part of building this persona of the ultimate winner. Michael: Precisely. Reilly found that many of these "championships" were senior or super-senior events, or he just declared himself the winner of the first round at a new course and called it a championship. One time, he didn't even play in the tournament at his Bedminster course. He was out of town, called the pro shop afterward, found out who won, and told the staff to put his name on the plaque instead because, he claimed, "I beat that guy all the time." Kevin: That is absolutely shameless. It's one thing to cheat, but it's another to steal someone else's victory. Okay, so he's a shameless cheater on the course. But how does that 'win at all costs' mindset show up in his actual business? Does it leave the fairway? Michael: Oh, it doesn't just leave the fairway. According to Reilly, it's the blueprint for his entire business empire.

Michael: Reilly argues that Trump’s business strategy, especially with his golf courses, can be boiled down to a simple, repeatable formula: "Buy, Lie, and Cry." Kevin: 'Buy, Lie, and Cry.' That's catchy. Break it down for me. Michael: Okay, so the 'Buy' part is straightforward. He often acquires distressed properties, like golf courses on the verge of bankruptcy. He gets them for a good price. The 'Lie' is where it gets interesting. This is the promotional phase. He'll pour some money in, add a giant, completely unnecessary waterfall, and then declare it the "best course in New York" or "better than Pebble Beach." He inflates its value to the public and the media to build his brand. Kevin: Okay, that's just marketing, right? A little hyperbole. Michael: It would be, except for the 'Cry' part. At the exact same time he's telling Forbes magazine that a course is worth, say, $50 million, he's suing the local town, claiming the course is over-assessed for tax purposes and is actually only worth a tiny fraction of that. Kevin: Wait, he's doing both at the same time? Michael: Simultaneously. The best example in the book is Trump Westchester. In his presidential financial disclosures, he valued it at "over $50 million." But for years, he was suing the local town of Ossining, arguing its real value was just $1.4 million to get a massive tax break. Kevin: That is a staggering difference. How can you even defend that? How can a property be worth both $50 million and $1.4 million? Michael: You can't. And that's Reilly's point. It's the same logic as the invisible chip-in. You create the reality that best serves you in the moment. For the public, it's a world-class, $50 million asset. For the taxman, it's a struggling, barely-worth-a-million-dollar property. He wants the prestige of the high value and the tax break of the low value. Kevin: But isn't fighting your tax assessment just smart, aggressive business? Where does it cross the line? Michael: I think Reilly would argue the line is crossed at the blatant, provable hypocrisy. It’s the pattern of deception. It's not just about taxes. This mentality extends to how he treats people he works with. The book is filled with stories of contractors, painters, and architects who were never paid in full. Kevin: Like the architect you mentioned earlier? Michael: Exactly. Andrew Tesoro, the architect for that same Westchester clubhouse. He did the work, submitted his bills, and Trump's organization just kept shorting the payments. When the final bill of over $100,000 came due, they offered him 40 cents on the dollar. When he finally got a meeting with Trump himself, Trump offered him just $25,000, basically 18% of what he was owed, and told him to take it or leave it. Kevin: And he had to take it, I'm guessing. Because suing would cost a fortune. Michael: That's the intimidation factor. You're a small business owner, a single dad like Tesoro was. Are you going to spend years and hundreds of thousands of dollars fighting a billionaire's legal team? Or do you just take the hit and move on? Most people take the hit. It's the business equivalent of throwing your opponent's ball in the bunker. You create a situation where they have no good options. Kevin: So the 'win at all costs' mentality is identical. On the course, he cheats to win the game. In business, he uses lawsuits and financial pressure to 'win' the negotiation, even if an agreement was already in place. Michael: And that pattern of deception, of prioritizing his brand and his wallet over the rules, is exactly what Reilly argues followed him straight into the White-House.

Kevin: Okay, this is the leap I've been waiting for. It's one thing to talk about a golf score or a business deal. It's another to connect it to the presidency. How does Reilly make that jump? Michael: He argues that Trump never stopped being a golf course owner. His presidency is run with the same priorities: what's good for the Trump brand and what benefits his properties. The book points to some deeply troubling potential conflicts of interest that seem to stem directly from his golf empire. Kevin: Such as? Michael: The most glaring example Reilly brings up is the initial travel ban on several Muslim-majority countries. When the list of seven countries came out, journalists and analysts immediately noticed who wasn't on the list. Kevin: Let me guess. Countries where he has business interests? Michael: Precisely. Countries like Saudi Arabia, Egypt, and the United Arab Emirates—all with documented ties to terrorism—were conspicuously absent. And where does Trump have massive, multi-million dollar golf resorts? Dubai, in the UAE. His business partner there, Hussain Sajwani, is a powerful tycoon. Reilly points out that Trump's decisions seemed to protect his business relationships, even if it made little sense from a national security perspective. Kevin: Wow. So we're going from a misplaced golf ball to potentially influencing foreign policy based on where he owns a course. That's a huge leap, but the pattern Reilly lays out is... unsettling. Michael: It's a pattern of self-interest. Another powerful example is his response to Hurricane Maria in Puerto Rico. The island was devastated. The federal response was widely seen as slow and inadequate. Trump was publicly feuding with the mayor of San Juan and tweeting about the island's "massive debt." Kevin: I remember that. It felt so callous at the time. Michael: Reilly provides some crucial context. Just two years before the hurricane, Trump's golf course in Puerto Rico, which he had licensed his name to, went bankrupt. It defaulted on a $33 million government bond, leaving the already-struggling territory holding the bag. So when the hurricane hit, Trump wasn't just dealing with a natural disaster; he was dealing with a place where his business had publicly failed and left a pile of debt. Kevin: So Reilly is suggesting his personal animosity and his failed business deal colored his response to a humanitarian crisis? Michael: That's the argument. That he sees everything—countries, people, policies—through the lens of his personal wins and losses. And this, Reilly concludes, has left a "big orange stain," as he puts it, on the game of golf itself. Kevin: A stain? How so? Michael: For years, golf has been trying to shed its image as a stuffy, elitist, rich-white-guy sport. People like Tiger Woods brought in a new, diverse audience. But Trump reinforces all the worst stereotypes. He drives his cart on the greens, a huge taboo. He's famously said golf should be "aspirational," meaning a reward for the rich, not a game for everyone. Reilly, who grew up playing on public courses, sees this as a direct assault on the soul of the game. Kevin: He's making it exclusive and dishonest, when the game's tradition is about honor and accessibility. Michael: Exactly. He's undermining the very values that make the game special.

Michael: Ultimately, Reilly's book isn't just about golf. It's a character study. It argues that the small cheats reveal the big ones. The way you behave when you think no one is watching, or when you think you can get away with it, is who you really are. Kevin: If you’ll move your ball a few inches in the rough to get a better lie, what will you do when the stakes are higher? When it’s not a five-dollar bet, but a tax bill, a business contract, or a national policy? Michael: That's the central question of the book. Reilly quotes his father telling him, "Remember, Ricky, golf is a gentleman’s sport." It's built on a foundation of integrity. You call penalties on yourself. You respect the course and your opponents. The book presents Trump as the antithesis of that spirit. Kevin: It makes you wonder. If golf is a 'gentleman's sport' built on honor, what does it mean when its most famous player is, according to Reilly, its biggest cheater? What does that say about the game, and maybe, about us? Michael: That's a heavy question. Reilly's conclusion is that it's a stain that will be hard to wash out. He's made the game synonymous with his brand of winning, which is often at odds with the truth. Kevin: It’s a powerful metaphor. The idea that character is consistent, whether you're on a golf course or in the Oval Office. The little things aren't so little after all. Michael: What do you think? Is it just a game, or is it a window into the soul? We’d love to hear your thoughts. Find us on our social channels and let us know. Michael: This is Aibrary, signing off.