Michael: I'm going to give you a number, Kevin: one dollar. That's how much a jury awarded Donald Trump after he sued the NFL for being a monopoly. One single dollar. It's a story that perfectly captures the man we're talking about today. Kevin: One dollar? That sounds more like an insult than a victory. What’s the story there? Did he frame the check? Michael: He might have! It was the result of his disastrous legal gamble with the USFL, a rival football league. He pushed the other owners to sue the NFL, and they technically won, but the jury awarded them a symbolic dollar in damages, which was automatically tripled to three dollars. The NFL sent a check for $3.76, which was never cashed. It was a total failure, but Trump later called it 'a great lawsuit.' Kevin: Of course he did. That’s an incredible level of spin. Where does a story like that even come from? Michael: It comes from The Making of Donald Trump by David Cay Johnston. And Johnston isn't just any author; he's a Pulitzer Prize-winning investigative journalist who's been covering Trump for nearly 30 years, longer than almost anyone. He wrote this book in just 27 days during the 2016 campaign, trying to distill three decades of reporting into a single, urgent profile. Kevin: Wow, 27 days. So this is less a leisurely biography and more of an emergency briefing. That one-dollar lawsuit story already tells me this is going to be a wild ride. Michael: Exactly. And according to Johnston, to understand the man, you have to understand the playbook. And that playbook all starts long before Trump was even born, with a family blueprint for bending the rules.

Michael: So, have you ever heard of Friedrich Drumpf? Kevin: Can't say I have. Sounds like a character from a Grimm's fairytale. Michael: Close. He was Donald Trump's grandfather. He emigrated from a small German village in 1885 at age 16, specifically to dodge mandatory military service. He lands in America and, like many, seeks his fortune. But his path was... unique. He ends up in the Klondike gold rush. Kevin: Okay, so he's a classic American immigrant story. Pulling himself up by his bootstraps, chasing gold. Michael: He was definitely chasing gold, but not by panning for it. Johnston uncovers that Friedrich opened a place called The Arctic Restaurant and Hotel. It was advertised as having fine food and lodging, but its real business, according to the book, was alcohol and prostitution. The rooms were tiny, mostly just a bed and a scale for weighing gold dust, and the "private boxes" for female guests were a core part of the business model. Kevin: Hold on. So the Trump family fortune began with a gold rush-era brothel? Michael: That's the picture Johnston paints. A story of pure opportunism. Friedrich saw a need—lonely miners with gold in their pockets—and he filled it, skirting the edges of legality and morality to build his initial wealth. He even built on land he didn't own. When the gold rush died down, he sold everything and left. Kevin: Okay, so the playbook is: find a boom, bend the rules, and get out before the bust. That sounds... disturbingly familiar. Michael: It gets more familiar. Fast forward a generation to Donald's father, Fred Trump. He builds a real estate empire in Queens and Brooklyn. But Johnston digs up some very uncomfortable stories. For instance, in 1927, a 21-year-old Fred Trump was arrested at a Ku Klux Klan rally in Queens that turned into a brawl with police. Kevin: Wait, his father was arrested at a KKK rally? How is that not a bigger story? Michael: Well, Donald Trump has vehemently denied it, saying it never happened, that there were no charges. But Johnston provides the newspaper clippings and public records. The charges were dropped, but the arrest is documented. It's a pattern Johnston highlights: when confronted with an inconvenient fact, deny, deny, deny. Kevin: And what about his business? Was it as clean as his son claims? Michael: Not exactly. Fred became incredibly wealthy by mastering government-subsidized housing programs after World War II. But he was investigated by the Senate in the 1950s for profiteering—essentially, for inflating his costs to get bigger government-backed loans and then pocketing the difference. The headline in the Brooklyn Eagle read, "But Trump has the surplus in his bank account." He was also known for having business ties with figures linked to the Mafia. Kevin: So the family blueprint is becoming clearer. It's not just about hard work; it's about leveraging systems, whether it's government subsidies or the needs of lonely miners, and associating with whomever it takes to get the job done. And if anyone calls you on it, you just say it never happened. Michael: Precisely. Johnston's argument is that you can't understand Donald Trump without understanding that he was born into this ethos. He wasn't just taught business; he was taught a specific, ruthless, and ethically flexible version of it.

Kevin: That idea of denying reality, even when the facts are right there, seems central. It feels like it goes beyond just business ethics. Michael: It absolutely does. And that brings us to the second, and maybe the most bizarre, part of his 'making': his genius for controlling his own story, sometimes by literally inventing people to tell it for him. Kevin: Inventing people? What, like imaginary friends? Michael: You're not far off. Johnston documents Trump's frequent use of pseudonyms, most famously 'John Baron' and 'John Miller'. These weren't just pen names; he would get on the phone with reporters and pretend to be his own spokesman. Kevin: You're kidding me. He called reporters pretending to be his own publicist? How did anyone fall for that? Michael: It sounds unbelievable, but it happened repeatedly for years. The most famous case is from 1991. A reporter from People magazine, Sue Carswell, was working on a story about his messy breakup with Marla Maples. She gets a call back from a man who identifies himself as 'John Miller,' a PR guy for Trump. Kevin: And let me guess, 'John Miller' had some very specific, very flattering things to say about his boss. Michael: Oh, you have no idea. 'Miller' goes on this long, rambling monologue, in a voice that sounds exactly like Trump's, saying that Trump wasn't leaving his wife for Marla, he was leaving for himself. He then starts listing all the famous women who are supposedly desperate to date him. He says, "He's living with Marla and he's got three other girlfriends... He's got Madonna calling, he's got Kim Basinger calling..." Kevin: This is beyond parody. It's like a plot from a bad 90s sitcom. He's literally creating his own hype machine with a sock puppet. But why? Why not just have a real publicist do it? Michael: That’s the key question. Johnston suggests it's about two things: total control and plausible deniability. He gets to plant the exact narrative he wants, in the exact Trumpian language he prefers. And if it blows up, he can just say, "That wasn't me." Which is exactly what he did. When the recording of that call was unearthed in 2016, he went on TV and said, "No, I don't think it was me, it doesn't sound like me." Kevin: Even with the audio evidence? That's next-level audacity. Michael: It's a core part of the brand-building. The brand is whatever he says it is, at any given moment. This extends to his wealth. In a deposition for that lawsuit against Tim O'Brien, the journalist who questioned his billionaire status, Trump admitted under oath that his net worth fluctuates. When the lawyer asked what it's based on, Trump said, "It goes up and down with the markets and with attitudes and with feelings, even my own feelings." Kevin: With his feelings? My feelings tell me I should be a millionaire, but my bank account has a different opinion. So his net worth isn't just about money, it's about his mood? Michael: According to him, yes. It's all part of the same strategy: reality is malleable. Whether it's his wealth, his romantic life, or his family history, the story is what matters, not the facts. And he was the master storyteller of his own myth.

Kevin: Okay, so we have a family blueprint for bending rules and a personal obsession with crafting a fictional brand. How does that scale up? What happens when this person starts dealing with entire systems, like the law or finance? Michael: That's where Johnston's reporting gets really chilling, because you see the real-world consequences. He applies that same playbook—exploit loopholes, deny responsibility, and prioritize the brand over everything—to much bigger arenas. Take Trump University. Kevin: Right, the "get rich quick" real estate seminars. I remember the ads. Michael: The ads were classic Trump. He promised to share his secrets to success, taught by "hand-picked" professors who were the "best of the best." He even claimed it was better than Harvard. The reality, as laid out in the book and numerous lawsuits, was a high-pressure sales operation. Kevin: So were people actually learning anything, or was it just a very expensive photo-op? Michael: For most, it was a path to debt. The "hand-picked" instructors were often people with no real estate success of their own, who were trained in aggressive sales tactics. The goal was to upsell attendees from the "free" seminar to the $1,500 weekend course, and then to the $35,000 "Gold Elite" package. The content was often generic, outdated information you could find online. It was branded as education, but it operated like a multi-level marketing scheme. Kevin: And he got away with it? Michael: For a long time. When state attorneys general started investigating, a pattern emerged. In Florida, Attorney General Pam Bondi's office was looking into Trump University. Shortly after, a political group supporting her received a $25,000 check from the Donald J. Trump Foundation. Soon after that, her office announced it would not be pursuing an investigation. A similar thing happened in Texas. Kevin: That feels... incredibly corrupt. Using a charity to make a political donation that seemingly shuts down an investigation into your business. Michael: It's a perfect example of exploiting the system. He understands where the levers of power are and isn't afraid to pull them. We see the same pattern with his taxes. Johnston details how Trump uses his golf courses for massive tax write-offs. Kevin: How does that work? Michael: It's a masterclass in having it both ways. For example, his golf club in Westchester, New York. In his public financial disclosures, he values it at over $50 million. But when he's arguing with the local tax assessor, he claims it's worth less than $1.4 million to keep his property taxes low. Kevin: How is that even legal? Valuing the same thing so differently depending on who you're talking to? Michael: It's about aggressively exploiting every loophole and then fighting it out in court. He uses conservation easements, where he promises not to develop land in exchange for a huge tax deduction, even on land that was probably undevelopable anyway. He even put a small herd of goats on his New Jersey golf course to have it classified as agricultural land, dropping the tax bill from $80,000 a year to just over $1,000. Kevin: Goats. Of course. It's not about paying your fair share; it's about winning the game against the taxman. Michael: Exactly. Whether it's the legal system, the tax code, or the media, Johnston's book argues that Trump sees them all as systems to be manipulated for personal gain. The rules aren't a moral guide; they're just obstacles in a game he's determined to win.

Kevin: So when you put it all together—the family history from the Klondike, the fake publicists, the system-gaming with taxes and Trump U—it feels less like a series of random scandals and more like a consistent, lifelong strategy. Michael: Exactly. Johnston's core argument, which he borrows from F. Scott Fitzgerald, is that "action is character." You don't need to psychoanalyze Trump; you just need to look at the pattern of his actions over decades. He treats everything—business, media, politics, even family—as a transaction to be won. Kevin: It's fascinating that the book received such a mixed reception. Critics praised its investigative depth, but many readers found the portrayal so relentlessly negative. Yet, it's all based on documented facts—court records, depositions, interviews. Michael: That's the paradox Johnston presents. The book shows Trump is not some outsider who came to break the system. He's a master of exploiting its existing weaknesses, someone who has been playing this game his entire life. He knows exactly where the cracks are because he's spent a lifetime prying them open. Kevin: And the book came out in 2016, essentially as a warning. It makes you wonder what we, as a society, value in our leaders. Is it the carefully crafted brand, or the verifiable actions behind it? Michael: It's a question that's more relevant than ever. Johnston's work forces us to ask: what are the 'making of' stories of the leaders we choose to follow? And are we paying enough attention to the details? Kevin: A great question to reflect on. We'd love to hear your thoughts. What was the most surprising story from Trump's past for you? The fake publicist? The gold rush brothel? The goats? Find us on our socials and let us know. Michael: This is Aibrary, signing off.