If Books Could Kill - The Art of the Deal

Episode Date: January 11, 2024

Before Donald Trump became America's most prominent politician and birth certificate inspector, he spent his days making everyone in New York City slightly uncomfortable. Michael and Peter discuss "The Art of the Deal," Trump’s 1987 bestseller chronicling his exploits as a celebrity slumlord. Where to find us: TwitterPeter's other podcast, 5-4Mike's other podcast, Maintenance PhaseSources:When Donald Trump Took Down Holiday Inns The Lost City of Trump Who Runs New York Now? How Donald Trump Bankrupted His Atlantic City Casinos, but Still Earned Millions Doer and Slumlord Both Donald Trump Gets What He WantsDonald Trump was a nightmare landlord in the 1980s Confidence Man: The Making of Donald Trump and the Breaking of America Thanks to Mindseye for our theme song!

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 Vermont in November or something. That is Central Park. Come on. Come on. I don't know. They don't have trees in New York. Have you heard of Donald Trump?

We, you deciduous motherfuckers over there. I have no idea what anything looks like. So it's funny, because 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. A lot of New Yorkers make them stick. 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 speeches. 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. And I'm not trying to give my comprehensive take on Donald Trump here.

Okay. 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 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 project. Oh yeah. Really digging deep, Peter. I do the work, you know.

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 bosos. That's like a whole section of airport bookstores. That's right. It's sort of distinct from 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 example are 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 gonna assume from context clues that that's a sports person, sports billionaire. My God, sports Richie Rich.

Robert Hergivic 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, banging them out. Kevin O'Leary has one called Cold Hard Truth on business, money, and life. He was on SNL, I know that one. Damon John has Ryzen 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-Agenra of like billionaires who have done reality TV shows.

Are we gonna do like the top chef hosts next? I just got 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. And it's just like in the middle of the book all of a sudden it's like a picture time.

Yeah. And it starts out with family photos and then then it's just like, Trump with various celebrities. I mean, that was CNC music factory. And then finally, it's just pictures of buildings. It's like, and here's what I built. And here's what I built. And here's what 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 J 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 inserts, it's 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 wanna 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. 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 in stock. Ho, tell, mo, tell. 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 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 and hostile takeovers were like all the rage, like I ever read Barbarians of the Gate. K-K-R, 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 in 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 percent of the company partially through backdoor channels to hide the purchases, which is illegal if you believe 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 to take over of the company. Okay. 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 allow it. I mean, that's probably the best comparison, right? These guys are just dicking around, doing like posturing, but with money. Yeah. 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. My understanding of his history is that he just left a wake of just unsatisfied and angry people. Like the people that marched on the Capitol on January 6th

and just got left with Joe Biden because Trump could not deliver for them. Chapter 2 is called Trump Cards, the Elements of the Deal. This is the only chapter that's actually setting out to give you affirmative advice. It's giving you his keys to deal-making. It's 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 in your 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. 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 saw, 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 jeans. 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 deal making, 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 back, deliver the goods, contain the costs, and have fun. Oh, God. Is enhanced your location, like, don't meet on their home turf? No, enhanced your location is his sort of response to the idea that in real estate, it's location, location, location.

Uh. 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 generic, like whatever, think big.

We're not gonna go through them all, but there are some threads I wanna 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 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 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. Funny story, at one point, he was about to be late on a debt payment. So his dad had a flunky by $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 alone, basically. Mr. Lawyer over here, okay? That's not just my opinion, the government said that that was a law firm. Okay. I just assume every type of lawyers knows all of the laws. So the Taj Mahal files for bankruptcy in 1991,

Trump Plaza in 1992. And it's actually like quite devastating for Trump financially. Not only were Trump companies in the whole $3 billion in change, but he had personally guaranteed nearly a billion of that. 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. 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 by 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. 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, just like 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 what. 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, let 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. 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. 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. But 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 media and liberals and like democratic politicians. But at his haters, he's talking about like 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 of paragraphs later, he says, I'm not going to kid you. It's also nice to get good reviews. Oh, well. It's so transparent. Yeah. 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, 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. I know 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's addicted? Or they said nice things to me?

I feel like this is why people think that he's an arsesist, right? Because like he has, 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 just like voting for you know, Medicare for all. There is something interesting about these guys where they're actually quite easy to manipulate. He has no like beliefs other than 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? What 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. 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 necessarily, right?

It's just like, well, fuck up. 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 with it. He's trying to distract us from whatever he'll do like some dumb tweet. Now, he's trying to distract us from whatever he'll do, like some dumb tweet. And 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 it than that. Like for example, he talks about embellishing. I'm, let me send you than 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 gonna have the best healthcare 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 in board that like Construction is moving along. Oh my God. And he's like bragging about this in the book. Right, 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, okay, 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 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, 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. Yeah.

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 accountability, 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 totes

and other forms of reward. You can sort of see the psychology of someone who lies a little bit, gets rewarded, lies a little bit more, gets rewarded. And it eventually builds to a point where you lose an election, and then you're just like, I won the election. Yeah, I got to know. And like everyone around you is like, yeah, you did.

I can't even say that I wouldn't do that. Yeah. 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. Yeah. I can't tell you for sure that I wouldn't do that. 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 weirdo. So listen to 115. Let's try 120.

Okay, one, 40. That's right. 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 we talked about them

in retrospect. And like 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 in general. And that's certainly what where I was. I'm not even sure that I know what like real estate development is. So that's a very funny part of the book

because my dad was a contractor. I wasn't that close to the industry. I think you could just read the whole book and not know what Donald Trump's job is. Because he's not doing the actual building. That gets contracted out. He's not really doing the financing. He gets financing from elsewhere.

All he is really is someone who like expedites things and makes sure that things are moving along. 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, 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. A whole world up, Peter, I don't know. We are artists and also scientists. Scalars and statesmen.

It's the opposite of a fake job. No one is creating more than we are. So, all right, I wanna start with the most emblematic deal. Have you ever heard of Trump City? Oh my God, no, but it sounds like Joe Bluttsing from the rest of the 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 political 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 we do you here. That's why I'm... 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. 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 depending on how much armchair psychology you wanna do, probably trying to impress his dad. Yeah. So in the mid-70s, company called Pen Central Railroads is in bankruptcy. And its various properties around New York City are being offloaded. Some of them are in prominent locations, so they're looking for like a developer with political connections. Trump is looking to make a name for himself.

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.

Third property is another set of old rail yards. These on the upper west side. Okay. Trump develops these 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 boards, seven, 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. And Trump swoops into buy it. Trump at this point, he's at the height of his success in his real estate career, right?

He developed the grand-hiot, 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.

We know that entails. Yeah. We're also coming out of an era where the city struggled financially. New York nearly went bankrupt in the mid 70s. So Trump is sort of a symbol of the city's rebound for better, 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 8,000 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. 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 on himself like sort of admits.

He's like, 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 gaze. This is taken forever. They start organizing. They get like celebrities like Jerry Seinfeld and others to raise money for lawyers. They also brought like Betty for Dan and the coalition of people who like stood against

Trump on this is fucking hilarious, dude. It's like all of these like 80s New York sort of 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 centers. They don't leave for Trump's new location.

Once NBC is out, Trump eventually changes the proposed name to Trump City. Okay. He's sort of at like a standstill. He's budding up against all these rich folks. And he sort of veers off into other ventures. He buys the plaza hotel for like $400 million, finance by debt, buys the Taj Mahal, by issuing like $700 million in junk bonds. You know, this is sort of what we touched on earlier. This is how he 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 put together by some like community organizations called Riverside South, which is what it's still called. That'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 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, we're, 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 in the 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 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. His big grotesque thing, and his style is like, ostentatious. You know, he, like, tacky as shit. By the way, there are a couple points in the book where he actually calls someone else's work, tacky. Oh, nice.

And he'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 gonna build the tallest building in the world and it's gonna be a New York City.

He is a kind of self-made man in the most parentheses derogatory way, but he just 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, yeah, yeah.

He's manipulating press members whose job is to not be subject to manipulation. Right, right, this is the whole job. If we're gonna 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 my parents still remember it. You know what I mean? It also shows that in one of the few times that people stood up to him, he just 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. This is one of the first bouts of bad press Trump ever got It's 1981. He buys a couple of buildings right along Central Park the Barbizon Hotel and 100 Central Park South which is a residential building His plan is to demolish the buildings the Barbizon Hotel and 100 Central Park South, which is a residential building. His plan is to demolish the buildings and replace them with some luxury monstrosity for rich burverts. 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. Yeah, the basics of what's happening here is Trump wants these people out so he can demolish the building and they wanna stay, right? Okay, 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 and 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, I may have been. Here's what I would have done.

Yeah, yeah. This is like the Uber driver that I had that was like some Uber driver sell Coke. You know, I don't know. Some people are out here. Can't say who. He goes on to say, the tenants at a hundred central park south

got an abundance of heat and plenty of hot water. What I didn't do was run a hundred central park south as if it were a white glove park avenue building. Okay. The rent role, 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 slub lord. Yeah. Yeah. I didn't provide luxury services, guys. Right. He's trying to tell a story of like, I 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, made the dormant dress in more casual uniforms to save on dry cleaning, replaced the light bulbs with lower wattage bulbs. That's basically it. This is like you listen to Yasha Monks 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 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 tenants. 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. Ask the superintendent to spy on the tenants. The superintendent's like, no, I'm not going to do that. And the guy goes, what are you, a born again Christian? 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 who's 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? 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 legal leave required? 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. Like let me tell you my side of the story, right? What happened with the tenants got a lawyer and suit Trump. Trump

suits them back for over a hundred million dollars. For what? What did he suit him 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 a hundredth central park south, because I still planted 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 truckload. I'm not going to pretend that it bothered me to imagine the very wealthy tenants of a hundred 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 departments 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 of 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. Right. It's very funny to be like, now what some slum lords do is they bring in a truckload of undesirables and then deep breath. So I brought in a truckload of undesirables and then deep breath. 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 buildings vacant units. Obviously, like everyone from the tenants to the press

just immediately calls this out as a gross ploy. Yeah, he's just leveraging home with 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. And therefore he's like, well, that fuck it. Right. So like, it's very funny to me that he frames it like this in a 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 like how repellent he is as a person. I think he also has a thing in his brain where business 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 you're no fault of his own at all.

Right, just absolutely did nothing. That 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. Right. 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 rent control, right?

And what makes it so Trump be in my mind is that like he doesn't have a coherent ideology. 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. And this slots into that framework, right? He opposes rent control because it's been an impediment to him personally. He's 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. 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 woman's rank, 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. 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's city, people have kind of credit him for. Like he will pivot if he realizes he's hit a wall. I do wonder if that instinct of his has faded over time. It's hard to tell because he doesn't admit defeat anywhere, right? But you can see by his actions that he understands when he's been like outmaneuvered.

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 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 the 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, there's sort of like a libertarian on economic issues, right? You want to like get rid of regulations because for most businessmen regulations are a big impediment. And one of the first ways that Trumpmen 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 a 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, 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 navigating politics and navigating bureaucracy

as 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 ourselves. 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. 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 has worked for him. It's also reminds me of like my career in human rights that way you've seen a lot of dictatorships is 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.

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 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?

He's hiring his own children. That's why he sought power, right? That is mine. 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 I 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. Uh, and so when our healthcare system needs work, the problem is you need better people.

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 Detokeville 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. The first like modern celebrity CEO in the vein of Donald Trump, I think was basically his contemporary Leia Cocoa. All 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. He basically becomes famous because he joins Chrysler when Chrysler is absolutely in the tank getting like government bailouts completely 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. When these started featuring Dave Thomas and his commercials, right? Then Microsoft and Bill Gates, that was sort of a novel thing to just have your CEO be out there.

Yeah, Colonel Sanders, Tony the Tiger. Importantly, for our purposes, in 84, he publishes an autobiography titled Iococca, An Autobiography, which is a best-selling sensation. Trump references Iococca 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 is taking cues from Iococca's celebrity. He's certainly like manufacturing celebrity

in a way that it feels like people in his position didn't really do before Leia Cokka, at least not to that extent. It's also maybe like the origin story of our show, and 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 has manipulated. Right. Tony Schwartz, the co-author here, is a business journalist. You're a business journalist who's laundering Donald Trump's version of events about his like slum lord behavior It's just a completely hollow segment of our media and I feel like Trump I a coca Jack Welch These guys come out of this like 80s milieu that like felt like the golden age of the great American asshole, you know 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 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 card style in the early 90s. And he's like, oh, I need to reevaluate, insulate myself,

and then branch out into just 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 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. Yeah. I really believe that his career along trajectory towards the presidency is just because Donald Trump believes that that's the most famous you can be. Yeah, yeah, also I mean to me that's why this is so much more a media failure story than anything else because I mean plenty of people want to become famous, right? But basically Trump gets this like media philatio for years and years and years where nobody presents him to the public as like just a fucking slum lord asshole. They present him as like, oh, a successful businessman. Like, he's kind of charming. 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? If Ted Bundy was worth like $500 million, they'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 gonna 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. It's 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? you