The Art of the Deal
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Michael. Peter. What do you know about the art of the deal? All I know is that I'm ready to confirm my suspicion that staging a coup is roughly half as bad as being a New York real estate developer.

All right. I am going to send you the cover of this book. Well, actually, why don't you describe to me what it says? Honestly, I sort of hate how good the graphic design is. It's a black background and gold letters, of course. And it just says in huge font, Trump, the art of the deal. And then the author is Donald J. Trump with Tony Schwartz.

And it's a photo of Trump in front of like Vermont in November or something. That is Central Park. Oh, really? Come on. I don't know. They don't have trees in New York. Have you heard of Donald Trump? We don't.

You deciduous motherfuckers over there. I have no idea what anything looks like. So it's funny because it's this. The book says Trump in big letters at the top. And I just sort of thought that was because Trump is the author and he was putting his name big. But actually what's happening is that the full title of the book is Trump, the art of the deal. I'm pretty sure it's Vermont, though, Peter. I see tall buildings in the background. Yeah.

A lot of New Yorkers make that mistake. The book comes out in 1988, co-authored by Tony Schwartz, who's basically like a business journalist. Pretty obvious that he's doing all of the writing here. It's not in Trump's voice. It doesn't have that Trump cadence. So it's not showing the early stages of dementia. That's right. The way that Trump's speech is. He very accurately draws a clock in the middle of the book, you know.

He's reciting the alphabet backwards at various points. So I want to level set a bit here because I guess this is theoretically a big topic. I'm not trying to give my comprehensive take on Donald Trump here. I want to accomplish a few things, hopefully. One, see if we can pull it any threads that explain Trump as we know him now. Two, I want to prod Trump.

around the period of Trump's life that made him famous. You know, despite all the media coverage, most people don't exactly know what Trump was up to back in the 80s. Right. Unless you lived in New York. I don't think you had like have your arms around exactly what he was doing. Yeah, it was for most of us outside of New York. It was nothing, nothing, nothing. Home alone, too, which I watched as part of my. Oh, yeah.

Really digging deep, Peter. I do the work. And third, I wanted to take our first step into the exploration of a genre of airport book that I sort of realized we haven't touched on, which is the book written by celebrity business bozos. That's like a whole section of airport bookstores. That's right. It's sort of distinct from like

the rich dad, poor dad genre, right? This is more like a subgenre of low effort celebrity memoir. Also, Art of the Deal is the perfect exemplar because so many of these books are neither written nor read by the CEOs on the cover. There are so many of these books. Yeah. Mark Cuban has one called How to Win at the Sport of Business. I'm going to assume from context clues that that's a sports person, sports billionaire, sports Richie Rich. Robert Herjavec has one called Driven, How to Succeed in Business and Life. That's a car related billionaire.

I'm doing, I'm getting all these, Peter. I'm banging them out. Kevin O'Leary has one called Cold Hard Truth on Business, Money, and Life. Oh, he was on SNL. I know that one. Damon John has Rise and Grind, Outperform, Outwork, and Out-Hustle Your Way to a More Successful and Rewarding Life. You made that up. No, I didn't. But I was just trying to see whether you watch Shark Tank because these are just the sharks on Shark Tank. So there's even a sub-sub-genre of

billionaires who have done reality TV shows. Are we going to do the top chef hosts next? Just go through all the reality shows? You know that our podcast is coming to an end if we ever do a cookbook and we're just like, this recipe sucks. One cup? More like one and a third.

Yeah. One of the hallmarks of these books is that they are often just like a series of anecdotes more than they are a cohesive story. That's what the art of the deal is like. It goes through some of Trump's early life and then it's just deals from then on. Like it's just one deal after another. There is also a lengthy photo insert section. There's just like in the middle of the book, all of a sudden it's like it's picture time.

Yeah, yeah, yeah. And it starts out with family photos and then it's just like Trump with various celebrities. I'm hanging out with C&C Music Factory. And then finally, it's just pictures of buildings. It's like, and here's one I built. And here's one I built. I'm going to send you my favorite, my favorite picture from the photo inserts. And it's my favorite because of...

The caption. It's a photo of a building and it says New York City's Jacob Javits Convention Center. I offered to oversee the construction, but the city and state went ahead on their own. Not surprisingly, the project came in years late and hundreds of millions of dollars over budget. So he's just like settling scores. It's like I didn't do anything. In the middle of the photo insert is just a picture of a building that he didn't build. And he's like, this building sucks.

But if I was involved, it wouldn't have sucked. It's so good, dude. It sounds like he has nailed the voice because that is like the weird mixture of like insecurity and resentment and just irrelevant information that Trump is very good at. You can tell that Trump was involved in the writing. Like it's like just a little too petty.

and weird to be the voice of Tony Schwartz, the co-author. The worst part about doing this episode is that I can only talk about Trump for so long before every part of my brain wants me to do the Trump impression that I can't actually do.

And then it becomes permanent. And then just every episode from now on. So I want to get into the substance of the book. It starts off with a sort of like week in the life thing. His timeline starts at 9 a.m. on Monday. And by 2 p.m., he's getting deposed. He says, nowadays, if your name is Donald Trump, everyone in the world seems to want to sue you. Yeah.

If you're a huge piece of shit for your entire life, that is true. People will come after you eventually. So the very first thing he does in like his little week is have a phone call about his purchase of Holiday Inn stock. Hotel Motel. And it's just like a quick aside about how he had purchased 5% of the company because he thought that their real estate assets were undervalued and he was considering a takeover of the company. I thought this was weird because this is like activist investor talk.

I don't know what you know about activist investing, but like...

You know, you buy a bunch of stock in a public company to the point where you have leverage over the company and you can either try to take over the company or just influence business decisions. Right. And I didn't know that Trump was ever in this game at all. This was a time when aggressive activists investing in hostile takeovers were like all the rage. Like if you ever read Barbarians at the Gate. KKR. Yeah. Yeah. Yeah. And this was like.

Before any of this shit got heavily regulated, it was like the Wild West. And so a lot of scumbags were in the activist investing game. So I looked into the Holiday Inn story. And what happened was that there was animosity between him and Holiday based on some prior dealings. So he buys 5% of the company partially through backdoor channels to hide the purchases, which is illegal if you believe that.

the story of the Federal Trade Commission. Then he attempted what was called green mailing. This is where you buy a bunch of stock, you go to the company and you ask that they buy it back at a premium or else you will attempt a takeover of the company. This is more or less illegal now. At the time, it was just considered slimy. Trump claimed in testimony that that's not what he was doing. But in the book, he pretty flatly says that this was what he was doing. So I'm not

This sounds like a form of sports to me, honestly, but I'll allow it. I mean, that's probably the best comparison, right? These guys are just dicking around doing like posturing, but with money. Holiday Inn attempts to defend from the takeover. They do that by making payments to shareholders, which puts them into debt. They end up like selling a bunch of properties and something like

2,500 people in Memphis, Tennessee lose their jobs. The lesson I took from this was that even behind like a couple of throwaway paragraphs about like a profitable stock sale in the very, very beginning of the book, there's a story about like white collar crime and average people just getting wiped out by this asshole, you know?

I do assume that every single anecdote basically comes back to this. There's not going to be any where you're like, oh, wow, he really created a lot of jobs. Right. My understanding of his history is that like he just left a wake of just like unsatisfied and angry people. Like the the people that marched on the Capitol on January 6th and just got left with Joe Biden because Trump Trump could not deliver for them. Check.

Chapter two is called Trump Cards, the Elements of the Deal. This is the only chapter that's like actually setting out to give you affirmative advice. It's giving you his keys to deal making. It's also there is also something kind of funny about other people reading these books. I mean, we talked about this with the 48 Laws of Power, but also like in your normal life, if you're a normal person, how much like deal making are you really doing? When I do a post on Twitter, I consider that a deal. Yeah.

I did trick my doctor into getting me a shingles vaccine, but that was just through like lying. All right. I just sent you something. He says, my style of deal making is quite simple and straightforward. I aim very high and then I just keep pushing and pushing and pushing to get what I'm after. Sometimes I settle for less than I sought, but in most cases, I still end up with what I want.

more than anything else. I think deal-making is an ability you're born with. It's in the genes. I don't say that egotistically. It's not about being brilliant. It does take a certain intelligence, but mostly it's about instincts.

God, he's weirdly insightful about himself. It's just like I have like a lizard brain sense of dominance. Yeah, no, I think I think that's right. I think that he has an understanding that he's not like a particularly smart guy. Yeah. You know, he says it's in the genes. He's said that in like various different contexts before. It feels like something that his dad told him when he was young. Yeah, you could even say it goes all the way back to Sir Francis Galton. So I want to go through his little rules for dealmaking.

Most of which are sort of self-explanatory. It says, think big, protect the downside and the upside will follow, maximize your options, know your market, use your leverage, enhance your location, get the word out, fight

Oh, God. Is enhance your location like don't meet on their home turf? No, enhance your location is his sort of response to the idea that in real estate, it's location, location, location.

Oh. He's sort of saying that's not actually true. You can, like, make your location better. You can improve it materially or you can just do PR. It's actually not paying contractors, not paying contractors, not paying contractors. So...

Some of these are, you know, generic, like whatever. Think big. We're not going to go through them all, but there are some threads I want to pull at because some of them are very distinctly Trump and I think do help explain his success in the real estate game. He says protect the downside and the upside will follow. This is interesting because I think it's something that Trump did do well, although it was a lesson that he only learned a

a few years after publishing the book. So I think everyone kind of knows that Trump's ventures into the casino business were fairly catastrophic, right? He finances them with junk debt, probably built too many too quickly. He's like betting on the revitalization of Atlantic City. For me,

Funny story. At one point, he was about to be late on a debt payment. So his dad had a flunky buy $3 million in chips at the Taj Mahal to like illegally infuse the place with enough cash to make the payment. Is that illegal? Yeah, it's like an off-the-books loan basically. Mr. Lawyer over here. Okay. That's not just my opinion. The government said that that was illegal. Okay. Find them. I just assume every type of lawyer just knows all of the laws. Yeah.

So the Taj Mahal files for bankruptcy in 1991, Trump Plaza in 92. And it's actually like quite devastating for Trump financially. Not only were Trump companies in the whole $3 billion and change, but he had personally guaranteed bankruptcy.

Nearly a billion of that. Oh, OK. The reason that Trump got in that hole was basically because he wanted to expand too quickly. And in the sort of like heat of all that expansion, he's like, all right, I'll guarantee that debt. Right. So he's like assuring his business partners that worse come to worse, they can come after him. Right. He's like, this is how confident I am in the deal. Like, I've got personal skin in the game. Right. So it's a way of getting financing. Right.

And so as part of the deal that he strikes with his creditors in bankruptcy, he delays all of his personal obligations to pay off the debt. And from there on out, he stopped personally guaranteeing large amounts of debt and let all of these corporate entities eat the risk. So in the mid 90s, he's using company money to like pay off his personal debts.

which you can do legally, basically, like Trump had the company buy properties that he owed money on, thereby sort of absorbing his debts. And the result of all this maneuvering in general is that when the companies get hit by bankruptcy, for example, Trump himself isn't very affected. It's the contractors and the shareholders and the employees who get hurt. Right. So credit to Trump for being honest here.

This is, in fact, the reason that he's still rich, right? There is a sort of snake-like intelligence in this. I mean, a lot of this is just stuff that rich people do. It's like the story of the structures that insulate rich people. You know, like the fact that you can lose billions of dollars and still be rich despite never having that money is like a product of the system that we've created, right? It's like,

You know, that's the cost of like fostering entrepreneurship or whatever. Right. And there are some people that just like latch on to that structure more aggressively than others. And Trump is just a good example of someone who, you know, bled it dry. Right. And it's an example of America's like reverse Spider-Man principle where it's like with great power comes less and less responsibility. Right. Right.

So one thing you'll notice very quickly when you're reading the section and the book generally is that even in the 80s, Trump's critics occupy like a way too large portion of his headspace. Oh, yeah. He says the other people I don't take too seriously are the critics, except when they stand in the way of my projects. In my opinion, they mostly write to impress each other and they're just as swayed by fashions as anyone else.

One week, it's spare glass towers they're praising to the skies. The next week, they've rediscovered old and they're celebrating detail and ornamentation. What very few of them have is any feeling for what the public wants.

Which is why if these critics ever tried to become developers, they'd be terrible failures. Who is he even talking about here? That's what's funny about this section is like now when he talks about his haters, he's talking about like the media and liberals and like Democratic politicians. But at this point, it's just like the New York Times architectural critic. So he has like all these complaints about critics. And then a couple paragraphs later, he says, I'm not going to kid you. It's also nice to get good reviews. Oh.

Well, so transparent, you know, he's just like, first of all, these guys, they don't know what the fuck they're talking about. They're a bunch of fucking losers. Second of all, please like my buildings. One of the sort of darkly fascinating things about Trump to me is that he does seem to judge other people exclusively on whether they're nice to him.

It's just like, well, how can you be saying that this person is a dictator? They said nice things to me. I feel like this is why people think that he's a narcissist, right? Because like he definitely has that. I also think this is the biggest mistake Democrats made. Right away, they should have just been like Trump rules. You know, if you just put me in a room with Trump over the course of his presidency, by the end of it, I could have had him as.

Just like voting for, you know, Medicare for all. Right. There is something interesting about these guys where they're actually quite easy to manipulate. Right. He has no like lasting beliefs other than like racial grievances, clearly. This conversation sort of feeds into how in the book he talks pretty openly and extensively about manipulating the media. It does sort of make it clear that he courts controversy on purpose. Right. Which I think we sort of I think most people had a sense of. But.

He talks about how he was criticized in the press for destroying some sculptures when he was building Trump Tower and how the bad press actually drove up sales. Right. He also has fight back as one of his elements of deal making. And what's interesting is when he articulates why he does it, it's sort of just like, well, I'm getting my view out there. Like they get to say what they want to say. Why can't I say what I want to say? Which is an interesting justification. It's not exactly strategic justification.

necessarily, right? It's just like, well, fuck him. One of my like enduring beliefs about Trump is that I don't think he's capable of a lot of strategic thought. I think people, people will often do this thing where they're like, he's trying to distract us from whatever. He'll do like some dumb tweet. They're like, he's trying to distract us from the Muslim ban or something. I really don't think that he engages in strategic thinking that much. I think,

It's mostly just like running on instinct. I want to push back a little bit against that because I think that part of this section of the book reveals that there's a little more to within that. Like, for example, he talks about embellishing. Let me send you something here. Okay. He says...

The final key to the way I promote is bravado. I play to people's fantasies. People may not always think big themselves, but they can still get very excited by those who do. People want to believe that something is the biggest and greatest and the most spectacular. I call it truthful hyperbole. It's an innocent form of exaggeration and a very effective form of promotion. Yeah, this is his thing of like, we're going to have the best health care plan or whatever. Like you just say these superlatives constantly. So he admits...

To stuff in the book that's like basically fraud. Like at one point, at one point he has construction crews pretend to do work to convince the Holiday Inn board that like construction is moving along. And he's like bragging about this in the book. He's just like saying it in the book. But my point is that I think that you leave this early part of the book being like, OK,

He's actually doing a lot of this stuff a little more consciously than it might seem. And just like you, I went into this basically believing that Trump is sort of a collection of impulses more than more than a guy. But I think you can see in the art of the deal that there's a little more to it than that. He's more purposeful than he sometimes appears, or at least at one point.

This was purposeful. And maybe now it's just purely, you know, purely reflex. I agree that people often ascribe way too much strategy to him. Like he's not trying to distract you from the Muslim ban. But I do think that he elevated the Muslim ban because he knew that that was going to get headlines. Well, I do wonder, like.

how much of this is kind of conditioned to. He just starts lying and then he's like, wait a minute, this works. This is another example of like how power works. I think all of us do this where you sort of test like, okay, what can I get away with with my boss, whatever. Everyone does this. But like when you're powerful and you're insulated from any form of accountabilities,

There's no reason for you ever to stop doing this. It's only escalation, especially as your wealth and power grows and you're more surrounded by like toadies and other forms of reward. You can sort of see the psychology of someone who who lies a little bit, gets rewarded, lies a little bit more, gets rewarded. And it eventually builds to a point where like you lose an election and then you're just like, I won the election. Yeah, everyone around you is like, yeah, you did it.

I can't even say that I wouldn't do that. Like, you know, you're just like playing a game with someone and you lose and you're like, I won. And everyone in the room is like, you won, sir. I can't tell you for sure that I wouldn't do that. Also, this is the same mechanism by which our episodes keep getting longer. I'm like, you fucking weirdos. I wasn't a 115. Let's try 120. OK, 130. It's all an experiment. No one's been like, hey, tone it down, Mike. All right. Let's talk deals, baby. Deal. The majority of the book.

It's just him talking about deals. And it's interesting to see how he talked about them in retrospect and what he thought he was going to accomplish at the time. I think most people's knowledge of Trump's business dealings is pretty vague and general. And that's certainly where I was. I'm not even sure that I know what like real estate development is. That's a very funny part of the book because like my dad was a contractor. I wasn't that close to like the industry.

I think you could just read the whole book and not know what Donald Trump's job is. Yeah. Because like he's not doing the actual building. Right. That gets like contracted out. Right. He's not really doing the financing. Right. He gets financing from elsewhere. All he is really is someone who like expedites things and makes sure that things are moving along. Right. It's almost like a weird middleman thing.

where he's like connecting like the money people to the architects, to the contractors. And he does promotion. Yeah, and then promotes it. But yeah, it is sort of like a fake job in the sense that like he's not really creating anything. You know, he's just sort of making sure that things are flowing. A thousand voices just screamed out in anger at a podcaster saying that someone else has a fake job. The whole world, oh, Peter, I don't know. We are artists and also scientists. Yeah.

Scholars and statesmen. It's the opposite. It's the opposite of a fake job. No one is creating more than we are. So, all right. I want to start with the most emblematic deal. Have you ever heard of Trump City? Oh, my God.

No, but it sounds like Joe Blutzing from Arrested Development. So this is a great introductory story for 1980s Donald Trump. Everyone under the age of 50 I spoke to had never heard of this. Everyone I spoke to who was like a boomer who lived in New York at the time.

remembers this vividly. Yeah. There was a great Politico piece from a few years ago about this by Michael Cruz that I'm cribbing from quite a bit. Oh, there was a video about plagiarism recently, so we need to make sure that we... That's why I'm otherwise... Usually I would not credit someone. Yeah, usually just read it verbatim. I've pieced together...

A story from history. So, all right. In the 1970s, Trump is like an up and coming real estate developer, mostly known because he's the son of Fred Trump, who was a prominent developer specializing in subsidized housing.

housing. Fred brings Donald on board basically right after college, makes him president of the organization by the time he's like 25 in 1971. He's working alongside his father. He's also trying to make a name for himself. And, you know, depending on how much armchair psychology you want to do, probably trying to impress his dad. Yeah. So in the mid 70s,

Yeah.

That's a good match. He gets the option to develop three properties. One is the dilapidated Commodore Hotel over Grand Central. He turns that into the Grand Hyatt Hotel, which it still is today. Second location is a set of old rail yards on the west side in Midtown. He sells that to the government so that they can build the Javits Convention Center, which he would include in his photo insert and complain about.

Which famously sucks shit because Trump wasn't involved. Yes. The third property is another set of old rail yards. These on the Upper West Side. Okay. Trump develops these like big grandiose plans for this plot on the Upper West Side. And if we fast forward a bit, this notoriously powerful local community board, Community Board 7, scuttles the plans. They're not going to let it happen. He gives up. Someone else buys the plot. But by the mid 80s, it's still not developed enough.

And Trump swoops in to buy it. Trump at this point, he's at the height of his success in his real estate career, right? He developed the Grand Hyatt. He developed the Trump Tower at about the same time. String of other properties, too. He's just started to branch out into Atlantic City. He's opening his first couple of casinos.

He's getting tons of press coverage, right? The New York Times is describing him as like a modern iteration of Robert Moses with all that entails. We're also coming out of an era where the city struggled financially. New York nearly went bankrupt in the mid-70s. So Trump –

It's sort of a symbol of the city's rebound for better or for worse. Right. And according to a lot of reporting and contemporaneous accounts, Trump thought that this plot of land on the West Side was going to be his crown jewel. He was going to do something like 8000 apartment units.

A massive shopping mall, a hotel, parking garages, parks. And the center of it, a 150-story tower, which would have been the tallest building in the world. And what is he going to call it, Peter? Well, initially, he calls it Television City because he wants to lure NBC to move their studios to the complex.

And this is basically where the book leaves off. That's like he's in the midst of this planning. He's like, yeah, this is going to be great. Lots of people have complaints about this proposal. Architectural critics hate it. People are concerned that it's like a walled off city within New York, which Trump himself like sort of admits he's like. Yeah.

You know, it's the mid 80s. He's capitalizing on fears about crime and safety. Yeah. And he's offering wealthy people like an oasis, right? Yeah. But you'll have a mall. You'll have your tall buildings. You don't have to even leave. Yes. All of the urban vibrancy of Saudi Arabia. Community board seven once again does not like it. And the wealthy and powerful and often famous locals don't like it. Just say elderly gays. This is taking forever. They start organizing.

they get like celebrities like Jerry Seinfeld and others to raise money for lawyers. Okay. They also brought like Betty Friedan in. What? Like the coalition of people who like stood against Trump on this is fucking hilarious, dude. It's like, yeah, all of these like eighties, New York sort of, uh,

Weirdos. The low rise mystique. They have a very powerful ally. Mayor Ed Koch does not like Trump. Famous elderly gay. Refuses to give him any tax breaks. And not only that, he gives tax breaks to NBC to keep them in Rockefeller Center so they don't leave for Trump's new location. OK.

Once NBC is out, Trump eventually changes the proposed name to Trump City. OK. He's sort of like a standstill. He's butting up against all these rich folks and he sort of veers off into other ventures. He buys the Plaza Hotel for like four hundred million dollars financed by debt, buys the Taj Mahal by issuing like seven hundred million dollars in junk bonds and

You know, this is sort of what we touched on earlier. This is how he like gets into severe debt. And that really weakens his hand in Trump City. He's sort of in a position where he needs to do something. His other properties are bleeding money. The interest rates are fucking crazy on his debt. And so what ends up happening is he's basically forced to accept this very modest proposal from

put together by some like community organizations called Riverside South, which is what it's still called. It's just a bunch of nice little buildings. And like the weird anti-climax to the story is that like Trump goes into a meeting, sees their proposal, and they're ready for him to be like,

get the fuck out of here. I'm going to build something disgusting here. And instead he's like, I love it. Let's do it. So a couple, a couple of things here. One is I was reading this and it's not the only time in the book, but it's, you know, one of a few times where you're like, wow, the rich weirdos in the upper West side are the most powerful people in the world. Yeah.

Yeah, we're currently struggling to preserve American democracy. But one thing we don't struggle to preserve in this country is the views of bodies of water from rich people's apartments. The story of Trump is really the story of like the media creation of Trump. And this sort of like puts his name on the map, I think.

for the median New Yorker. In the late 70s, early 80s, he goes from just being this like rich kid with connections to the most talked about developer in New York City, in large part because of this deal where he just gets the option to develop these properties and combining that with someone who clearly likes to self-promote, right? Yeah. Building a tower, what am I going to call it? What else would I call it? Trump Tower, right? Sure, yeah. This big grotesque thing he's got and he's

His style is like ostentatious, you know, like tacky as shit. By the way, there are a couple of points in the book where he actually calls someone else's work tacky. And it's like, Jesus Christ, what did it look like? He's like a gold toilet, really? Isn't that a little much? He talks about this in the book. His ambition brought a lot of headlines because he would just be like, I'm going to build the tallest building in the world and it's going to be in New York City. He is a kind of self-made man in like the most like parentheses derogatory way, but

That he just like he invented himself as a fucking celebrity despite never really doing anything. Exactly. Self-promotion doesn't work on its own. He's not standing on a street corner shouting into a megaphone about his sweet tower. Right. Yeah. He's manipulating press members whose job is to not be subject to manipulation. Right. This is a whole job. If we're going to have like, quote unquote, savvy journalists, this is the shit they need to be savvy about. The fact that a guy can be like, I'm going to build the tallest building in the world.

And basically get absolutely nowhere. But like my parents still remember it. You know what I mean? It also shows that like in one of the few times that people stood up to him, he just like took it and moved on. That's actually a lesson you can learn from the book or at least reading about the shit that he talks about in the book. There's another example of people standing up to Donald Trump. This is 100 Central Park South.

Okay.

And replace them with some luxury monstrosity for rich perverts. The problem is that 100 Central Park South is a rent controlled building, meaning that the like 60 or so tenants there were paying like well below market in a beautiful location. And therefore they are extremely inclined not to leave.

They lawyer up and things get very ugly, very quickly. And one of my favorite parts of the book is reading Trump's description of how this happened and then going to the public record and finding out what actually happened.

So I'm going to send you something. You know, the basics of what's happening here is Trump wants these people out so he can demolish the building and they want to stay. Right. OK, so he says it happens to be very easy to vacate a building if, like so many landlords, you don't mind being a bad guy.

When these landlords buy buildings they intend to vacate, they use corporate names that are difficult to trace. Then they hire thugs to come in with sledgehammers and smash up the boiler, rip out the stairways, and create floods by cutting holes in pipes. They import truckloads of junkies, prostitutes, and thieves and move them into vacant apartments to terrorize holdout tenants. That's what I call harassment. I wouldn't have done that sort of thing for moral reasons, nor would I have done it for practical reasons. I buy buildings in my own name, and I have a reputation to uphold.

This guy's not doing the truckload of junkies and prostitutes. You know what? This is a whole paragraph being like, look, if I were a bad guy, maybe here's what I would have done. Yeah. Yeah. This is like the, uh, the Uber driver that I had that was like some Uber drivers sell Coke. You know, I don't know. Some people are out here. Uh,

Can't say who. He goes on to say, the tenants at 100 Central Park South got an abundance of heat and plenty of hot water. What I didn't do was run 100 Central Park South as if it were a white glove Park Avenue building. Okay. The rent roll, which barely covered my basic expenses, simply couldn't support luxuries. Nor did tenants paying tiny below market rents have any right to expect them. Okay. This is like I'm a slumlord. Yeah. Yeah.

I didn't provide luxury services, guys. Right. He's trying to tell a story of like, look, I didn't do shady things to harass them out, but they pay below market rents, which only gives me so much money. So I had to lower the quality of services. No choice. He claims that he basically just like reduced some basic services and

This is like you listening to Yasha Monk's anecdotes of like, they're segregating the kids. And you're like, all right, let's just get to the part where we find out what really fucking happened. What do we know about this?

Well, look, if you if you believe the lawsuits filed by both New York City and New York State, what Trump actually did was threaten the tenants with imminent demolition, drastically decrease essential services, persistently delay in repairing defective conditions with life threatening potential and instruct employees to obtain information about the private lives and sex habits of

Holy shit. Yeah, that's based on testimony from the superintendent who said someone from the management company that Trump hired, which, by the way, Trump says in the book, specialized in relocating tenants. Asked the superintendent to spy on the tenants. The superintendent's like, no, I'm not going to do that. Yeah. And the guy goes, what are you, a born again Christian? Yeah.

How is that the one time you don't use the Jersey accent? So to give some specifics, the previous owners of the building had allowed tenants to make renovations, including things like knocking down walls in some cases.

Some tenants had done it in some cases like decades prior, like people there were people whose like parents lived there and they had inherited it and their parents had made renovations. Right. Trump demands that they undo the renovations in 12 days or be evicted. Oh, wow. Like we're talking about walls that would need to be replaced. Right. Yeah. The tenants claimed that he turned off hot water and heat during the winter, stopped all repairs, allowed a rodent infestation.

One elderly woman with emphysema said that they did construction that filled her apartment with dust. Jesus. He tried to evict a tenant for nonpayment of rent when it turns out the guy had in fact paid. Oh, that happened to me once. There was another tenant that they tried to evict.

But they didn't give adequate notice to him, the legally required notice. Here's what Trump says about that. He says, in another situation, we failed to give a tenant sufficient legal notice of an impending eviction proceeding. Our case was legitimate, but the court ruled that we should have known the law had been changed recently to require longer notice. Was it a legitimate case or did you not give him the legally required notice? You know what I mean?

When you're reading this section, you very quickly realize that what actually happened here is that Trump got a shitload of bad press for all of this. And this is like his effort to do damage control. Let me tell you my side of the story. Right. What happened was that the tenants got a lawyer and sued Trump.

Trump sues them back for over $100 million. For what? What did he sue them for? He alleged that the tenants and the lawyers were extorting him, that the lawyer was engaging in racketeering in violation of the RICO predicates. Nice. That suit gets tossed out pretty quickly. Here is what...

stirs up the most controversy. We're at the controversial part. He says, I had more than a dozen vacant apartments at 100 Central Park South. Because I still plan to demolish the building, I had no intention of filling the apartments with permanent tenants. Why not, I thought, offer them to the city for use by the homeless on a temporary basis. He's doing the truck

I'm not going to pretend that it bothered me to imagine the very wealthy tenants of 100 Central Park South having to live alongside people less fortunate than themselves for a while. I genuinely felt it was a shame not to make use of a few vacant apartments when the streets were filled with homeless people. Oh, out of the goodness of his heart. He's trying to cast them as like wealthy elites. Some of them actually were quite rich. Others were elderly folks on Social Security. So he tries to like paint this picture in the book as

rich people who didn't want to move because they had it too good. Right. And that's not like a totally unfair statement about some of the folks there. But even within the book, he admits that some people there were just not quite well off. It's very funny to be like, now what some slumlords do is they bring in a truckload of undesirables and then deep breath, startling.

So I brought in a truckload of undesirables. Like you didn't have to say the first part. So Trump takes out newspaper advertisements saying that he would house homeless people in the building's vacant units. Obviously, like everyone from the tenants to the press just immediately calls this out as a gross ploy. You know, he's just leveraging homeless people to scare off the tenants. He quickly follows it up with this paragraph. He says...

It didn't help make my offer seem sincere when one columnist wrote a story saying that I'd refused a subsequent plea by a group representing Polish refugees seeking to use the apartments. In fact, by then I'd had second thoughts about the whole concept.

My attorneys had researched the situation and determined that if I permitted anyone to move into the apartments, even on a temporary basis, I'd have a very hard time ever getting them out legally. So here's what's happening. After he takes out the newspaper ad, a group representing Polish refugees says, hey, we could use the apartments for refugees. And Trump declines. And the reason that he's giving for that.

Is that he learns that the homeless folks might end up having tenants' rights themselves. Oh, yeah, yeah, yeah, yeah, yeah. And therefore, he's like, well, then fuck it, right? So, like...

It's very funny to me that he frames it like this in the book. Like, bro, you can say whatever you want. It's your book. No one's fucking fact checking this. And even in his telling, he sounds like an absolute fucking scumbag. But then that's also part of his weird psychology too, right? It's almost like he doesn't seem to understand like how like repellent he is as a person. I think he also has a thing in his brain where business is,

is like a justification for an enormous amount of misconduct. To be fair, that is the ideology of like our entire economy. So he's not wrong in thinking this. Yeah. So at the end of all this, the tenants basically successfully hold out and Trump still ends up making money because the property value basically just goes up while he's holding on to the building. And so he's like,

It was a winner, you know, like I did great. Just through no fault of his own at all. Right. Just absolutely did nothing. He's at the end of the day, a lot of his early success especially is like, well, he's buying New York City real estate in the late 70s and early 80s. So like even when things go wrong, you're fine.

Right. This is why, like every boomer thinks they're a financial genius. Right. There's also a very Trumpian thing in this chapter, which is that he spends several pages just railing against rent control. Oh, yeah, of course. That it like tends to benefit the already well off, that it restricts housing supply. This is what more libertarian minded folks say about Trump.

Rent control. Right. And what makes it so Trumpy in my mind is that like he doesn't have a coherent ideology. Yeah. His beliefs are just sort of like a patchwork of grievances that he has personally experienced. Right. So like it's not as though he opposes rent control.

because he's a free market guy. Right. And this slots into that framework. Right. He opposes rent control because it's been an impediment to him personally. Yeah, he's a fucking landlord. That's why I feel like Trump is like the quintessential reactionary. Right. Because he's really only engaging with what's directly in front of him. Like every grievance feels sort of compartmentalized. You know, this is like us being in support of a law that makes it illegal to write emails complaining about other people's upspeak.

Like, look, just my principled beliefs lead me to this conclusion. I don't do that. So he does talk about other deals in this book. They're not quite as interesting. He loves talking about Wollman's Rink, the ice skating rink in Central Park, because

Basically, the government was handling it. They were doing a terrible job over budget, too slow. He takes over, does it quickly, does it under budget. He evicts a bunch of the kids that are skating there. Fuck out of here. Bring a bunch of homeless skaters. Even when he sort of fails objectively to achieve his goals, he sort of just sort of pivots and reframes it at the end. And that's something that like, for example, with Trump City, people have...

kind of credit him for it. Like he'll he will pivot if he realizes he's he's hit a wall. I do wonder if that instinct of his has has faded over time. It's hard to tell because he doesn't he doesn't admit defeat anywhere. Right. Yeah. But you can see by his actions that he understands when he's been like outmaneuvered. Right. But I think the fact that he hasn't admitted that he lost the election.

feels relevant here. Yeah, we've gone from Trump city to Trump country. It's real, real progress. Renaming the whole nation Trump country. If there was a nationwide referendum, I would vote yes, because I feel like we deserve it. It's accurate at least. Yeah. This sort of segues into this thought that I had throughout the book about Trump, which is like one of the things that makes him an outlier is that usually when a business guy shows up on the political scene,

They're sort of like a libertarian on economic issues, right? They want to like get rid of regulations because for most businessmen, regulations are a big impediment. And one of the first ways that Trump distinguished himself as a presidential candidate was that he didn't do that too much.

Instead, he's like talking about a more hawkish trade regime, right? Like more aggressive government involvement in the economy, which is weird because he does seem to have all the ingredients of an anti-regulation crusader. He comes out of like the most heavily regulated industry. Right. And he's constantly talking about fucking zoning laws that get in the way and all sorts of shit. Right. But I think what's happening is that he views like navigating politics and navigating bureaucracy is like part of the game and something that he's good at.

His father, keep in mind, made his bones in federally subsidized housing. And on top of that, had extensive political connections in New York. Trump himself received a bunch of government subsidies and tax breaks, sort of like built his early career on the back of his dad's political connections. And when you read through some of these deals, you can see that he takes pride in his ability to like navigate bureaucracy. Like it was always a running gag that he'd be asked

how he was going to solve complex problems. And he'd respond that he'd be like hiring the best people, which I thought at the time was just his way of dodging questions. Right. But then you read the book and you're like, actually, I think this is how he thinks problems are solved. Like when he does woman's rink,

He like goes to Canada to find people who specialize in making the ice, you know, like he really views problem solving as like you find the best people, you hire them and you put a lot of pressure on them. Right. So a lot of the things that he said in 2016 that previously clocked to me as him just

bullshitting now registered to me as him more like honestly relaying his plan, even if it's just a dumb plan, because like that is that has worked for him. It's also reminds me of like my career in human rights that way. You see in a lot of dictatorships is like,

corruption is basically an opportunity for entrepreneurship that a lot of these like low level civil servants, basically what they do is like, well, I can expedite the permitting process for you. I think Trump like understands this on some level that like if you got rid of these regulations, there's no real reason for a lot of these things to exist. And it basically destroys this like rent seeking sector of the economy. Yeah, I think it's an interesting angle. I think that

Trump doesn't really understand corruption as a concept. Right. The definition of corruption is the use of entrusted power for private gain, which is something Trump did constantly in office, right? Like he's hiring his own children. That's why he sought power, right? In his mind, this all flows naturally. Yeah, exactly. And it's sort of,

Like there's almost like this confusion, like, well, why wouldn't I be using this power for my private gain? Like that's the reason to have the power. Right, right. He struggles to view anything as systemic. Yeah. And that's why, again, I think he's the quintessential reactionary where almost everything is atomized. So when the zoning board is interfering with his project,

The real problem isn't that the zoning board's power is too broad in his mind necessarily. The real problem is that the zoning board doesn't like his project. They're stopping me from getting what I want. Right. Yeah. And so when our health care system needs work, the problem is you need better people. Yeah. Right. Everything is compartmentalized. Everything exists in a vacuum. There's no systemic change because there are no systemic problems. Right. The last thing I want to talk about is.

You know, when I was reading this book, I kept thinking to myself, like, when did this type of guy become a celebrity? Yeah. Right. Like, why did a market for this book even exist? Developing buildings has to be the straight up most boring type of business on Earth. Right. Right. I tried to trace the origin of like the celebrity businessman as far as I could. And I honestly can't find.

a clear lineage. Yeah. Like de Tocqueville was writing about Americans admiration of entrepreneurship in the fucking 1830s, you know? And then like the ultra wealthy families of the Gilded Age had like some level of celebrity, uh,

The first like modern celebrity CEO in the vein of Donald Trump, I think, was basically his contemporary, Lee Iacocca. Oh, right. GM guy? Chrysler guy? Chrysler. Right. He was an executive with Ford. He is well known for developing the Mustang. He has a falling out with whatever Habsburg grandson of Henry Ford is in charge of the company at the time and gets fired. Right.

He basically becomes famous because he joins Chrysler when Chrysler is absolutely in the tank getting like government bailouts.

turns the company around. Not only that, but he becomes the public face of the company in a way that was like fairly novel. Like he was appearing in TV commercials. He's making like media appearances on talk shows. He is often credited for like the trend of really public facing CEOs. Like Wendy's started featuring Dave Thomas in its commercials. Right. And then Microsoft and Bill Gates, like that was sort of a novel thing to just have your CEO be out there.

Yeah. Colonel Sanders, Tony the Tiger. And importantly for our purposes, in 84, he publishes an autobiography titled Iacocca, an autobiography, which is like a bestselling sensation. Trump references Iacocca a bunch in The Art of the Deal. They went into business together on a relatively small property in 1986. So I think it's like safe to say that Trump –

It's also maybe like the origin story of our show in that what we're documenting is the rise of this kind of ideas industry and like these thought leader dudes that are basically full of shit end up selling these airport books.

It seems like it's wrapped up in this thing where it's not enough to be a CEO anymore. All of these fucking guys want to be like influencers. Right. I also think there's a degree to which these guys learned how easily the business press is manipulated. Yeah. Tony Schwartz, the co-author here, is a business journalist. You're a business journalist who's laundering Donald Trump's.

Yeah. Yeah.

I feel like this whole thing was leading up to you getting that tagline out. That's good. The thought I kept having while reading this book is just like, why would anyone read a book about this fucking guy building buildings? Yeah. It's this combination of Trump's talent for self-promotion and also an American culture and media ecosystem that is ready to just like swallow it whole. It's also dark because this book comes out back when there was at least a case

for Donald Trump being a successful businessman, like he was doing actual business shit. Whereas after this book, he basically primarily focuses on being a celebrity. This book is like the culmination of a period in his life where he believed that he was infallible. And that's why things start to unravel because he's like, oh, I can take on a billion dollars in debt to like buy the plaza and casino. All of this starts falling apart. House of Cards style in the early 90s.

And he's like, oh, I need to reevaluate, insulate myself, and then branch out into just something

slapping my name on whatever fucking trash anyone is willing to buy, right? And none of this seemed to affect his public reputation either. His reputation was always as like a successful businessman, even though for most of the time that we knew him as a public figure, he wasn't meaningfully doing business shit. He was just like licensing his name to stuff. It seems pretty clear that he's obsessed with the idea of celebrity. And so once he achieves that, why focus on real estate, right? Real estate was a stepping stone to get famous. I really believe...

his career long trajectory towards the presidency is just because Donald Trump believes that that's the most famous you can be. Yeah. Also, I mean, to me, that's why this is so much more a media failure story than Trump's

anything else? Because, I mean, plenty of people want to become famous, right? But basically, Trump gets this, like, media fellatio for years and years and years where nobody presents him to the public as, like, just a fucking slumlord asshole. They present him as, like, ooh, a successful businessman. Like, ooh, he's kind of charming and he makes jokes or whatever. I mean, America's willingness...

to hoist up wealthy sociopaths and just describe them as brash and eccentric. Telling it like it is, yeah. Right. It really goes to show if you have a certain amount of money, there is no behavior that won't get whitewashed by the press, right? Right. If Ted Bundy was worth like $500 million, there'd be like a Newsweek piece that's like,

The millionaire with an interesting view about human life. I think to me the most striking thing about going through this book is how early he figured out this media cheat code. Like you mentioned, part of his job as a real estate developer is to promote the buildings. Yeah. You can just say, oh, we're going to build the tallest building in the world and then get a bunch of headlines and a bunch of attention. And like getting attention is kind of your job in that role.

And then it seems like over time, because that's basically the only thing he's ever been good at in his entire life is like getting attention and manipulating the media. Right. The media continues to give him attention, even though getting their attention is kind of his job and is like a way of enriching him.

And as politicians have come to resemble celebrities more and more, it sort of makes sense that he would drift into politics. Right. The combination of like the incentives of media and his own weird like personality flaws sort of perfectly collaborated to create this monster that like might end up winning again in 2024. And I look forward to living...

in 2025 in Trump's America or America by Trump. What do you think sounds better?