‘Lucky Loser’ Authors Russ Buettner and Susanne Craig Expose Truth About Trump’s Wealth and Success

In 2016, shortly before the presidential election, New York Times reporter Susanne Craig was anonymously mailed a copy of Donald Trump’s 1995 tax records. The long sought-after documents revealed Trump declared losses of almost $1 billion that year. The resulting story, published with several Times colleagues including Russ Buettner, would kick off a spectacular run of reporting that would help turn the image of Trump as a successful businessman on its head and earn Craig and Buettner a Pulitzer Prize along the way.

Craig and Buettner are now out with a new book, Lucky Loser: How Donald Trump Squandered His Father’s Fortune and Created the Illusion of Success, which they discussed with Mediaite editor in chief Aidan McLaughlin on this week’s episode of Press Club.

“I think in one or two of those years, we found that he lost more money than any other individual taxpayer in America,” said Craig about their initial story on Trump’s taxes.

Despite his business failings, Trump was repeatedly bailed out by what Craig and Buettner describe as several lucky breaks, the biggest of which was an inheritance from his father, Fred Trump, worth more than $400 million in today’s dollars. That windfall, which Trump has always denied receiving, was also first reported in the Times.

Another major break: Trump’s deal to host NBC’s The Apprentice in 2004, the hit reality show conceived of by Survivor producer Mark Burnett that ended up making both Burnett and his star Trump millions of dollars.

Lucky Loser tells the incredible story of what happened when The Apprentice crew first arrived at Trump Tower, at a time when Trump was not nearly as wealthy as he claimed to be. “The carpet smells like it’s full of mold. They’re expecting this hub of worldwide activity. And there’s no computer. There are no blueprints,” Buettner said. “There are just piles, very orderly piles of newspaper clippings and magazine articles about one subject. Donald Trump.”

Trump’s campaign has already responded to Lucky Loser, calling for it to be “repurposed as toilet paper.” Glowing reviews, which have labeled it a “first-rate financial thriller,” say otherwise.

Buettner and Craig gave their own thoughts on Trump’s response to the book — as well as his legal threats against them over their reporting — and discussed what they found when they dug into his lifetime in business, politics, and the media.

Mediaite’s Press Club airs in full Saturdays at 10 a.m. on Sirius XM’s POTUS Channel 124. You can also subscribe to Press Club on YouTube, Apple Podcasts, or Spotify. Read a transcript of the conversation below, edited for length and clarity.

Aidan McLaughlin: Tell us why you set out to write this book.

Susanne Craig: I think this book actually starts as a story in the New York Times newsroom. Russ and I were working in the metro section in 2016, I was down at City Hall, I’d actually just landed down there from Albany. I was City Hall bureau chief. I’d been there about three weeks, and I got a call saying, Donald Trump’s entered the race and we’d like you to write a story. In my case, I was looking at just what he owned or didn’t own in New York. There wasn’t a lot known about his businesses at the time. It’s a privately-held company. There’s not a lot of people there. And Donald Trump had promised he was going to release his tax returns, we were waiting for that.

But Russ and I each dived into different aspects of his career and started looking at it. We did that throughout 2016, and we just kept finding different stories. And then one of the significant stories we found, because Donald Trump never did release his tax returns, is one afternoon I was in the newsroom in September of 2016, it was a Friday afternoon. And I went to my mailbox and there was a manila envelope there. And inside of it was three pages of Donald Trump’s 1995 tax returns. And we didn’t know if it was true or not. We had a lot of work to do to confirm it.

But when we looked down and it looked like his losses for that year totaled almost $1 billion, we couldn’t believe it. And we worked around the clock. We were able to confirm it. We got it to press. And then we just kept reporting on his finances. We got a lot of information on his father’s finances and how much money his father had. And that turned out to be a lot of the money that Donald Trump inherited.

And we found out there was tax fraud that went on, and that was from a trove of documents that Mary Trump had given us. At that point, nobody knew she was the source and some additional reporting we did resulted in a story in 2018. And then we just kept going. We got a lot more tax information. And then Russ and I, in 2020, we realized we had a huge amount of information, but we felt like it was a skeleton of an actual narrative that we could tell in book form. And so we started out on this book.

At the time, in 2015, Trump’s run wasn’t really being taken seriously. What did you think when you were assigned this story looking into his taxes? He was famously secretive about his money and how he made it.

Buettner: Part of that happened in a short window because he had not been taken seriously. There was a very large field in 2015, massive. And there was no thought that he would be dodging through that, through experienced politicians who had more money, who had better operations already built. But he did. They devoured themselves.

And all of a sudden in spring, early spring of 2016, there was a collective realization that this was really serious. It was going to be him. And we had a man who was almost 70 years old who was basing his campaign on a 50-year history in business that no one really knew anything for sure about. So that was a huge vacuum to step into. And we don’t usually scrutinize presidential candidates who have that much time with no actual, real documented record. There was just what he said and no way to really check it. And as we’ve all learned, there’s a huge gap between what he says and the truth of things.

It’s easy to forget, but the Holy Grail of reporting at the time was the tax returns.

Craig: It’s funny, because I think of all the stuff we’ve gotten, but I remember that moment where we were able to get those three pages.

What did that feel like?

Craig: It was just such a huge moment. It was explosive. And the reaction, we’ve gotten other stuff, but that story always to me seems like the one that was just like, wow. And I think the other thing to remember about Donald Trump, when he became the Republican nominee, we hadn’t really seen a president in history who had finances that were as complicated as this, where the conflicts were just myriad, that we could see even without having his taxes. And so it was really important to the paper to get under this, but just to even try to get our hands around it in that short period of time was a lot. And that’s why we spent so long doing it.

One of the big themes of this book is that Trump is not the self-made man that he claims to be. He inherited nearly half a billion in today’s dollars from his father, Fred Trump. How did you figure that out?

Buettner: That was our 2018 story. We obtained a trove of family financial records. It’s since come out by her own accord that Mary Trump, Donald Trump’s niece, supplied those records to us. We also did a massive scrape for property records and his sister’s financial disclosure records.

And we were able to put that all together and make basically a massive spreadsheet with inflation adjustments, modified if he had invested in the S&P 500, to come up with a grand tally through the years, year by year of everything his father had given him and when.

And then that really showed us the various ways that his father had given him money, some of which was loans that were supposed to be repaid and never were. Some of it was just actual gift money. Some of it was trust funds. He created his first trust fund when Donald was three years old that made Donald and his siblings the owner of land under some of Fred Trump’s buildings. And then he paid them rent for the rest of their lives to their trust funds.

Must be nice.

Buettner: Some of it was when Donald orchestrated, after their father had died, the sale of the entire empire, which brought in what the banks basically valued at close to $1 billion then. So that was a big undertaking. But with all of these things, there’s a story to it that we never could really tell before this book. There’s a huge succession battle in that family. And that’s a huge part of Donald Trump’s life and who he became. And in that, you really see, even at a young age, the person that you would later see in the White House who seemed to just pop out of nowhere.

That’s the best part about this book, that it really captures the origin story of the Donald Trump that we know today. You’re reading through it and so much that you see explains the man that we saw in the White House. What did you think when you were reporting out this book about what it showed about Trump’s origin story and the man that it made?

Craig: We knew a little bit about Donald Trump, we’ve read some books on him that have been written before. But when we really started digging into the reporting, you start to see, like you said, the origin story. There’s a couple of anecdotes that right away come to mind.

One of them is the Trump family was quite wealthy and they belonged to a beach club near their place. And they would go there and play cards. They had a nice cabana on the beach. And one of the other members who was there, he was around Donald’s age. He said he would remember Donald Trump would get to the pool and he would go up high on the diving board. And as people were going by the pool fully dressed, he would cannonball from the diving board and just spray everybody. And then he would deny it. Sandy, the kid, now Donald’s age, that we talked to said, “He would deny it, but I saw it!” And that was one.

And then there was another one, because of all of Donald Trump’s hijinks, he gets sent famously to the New York Military Academy just outside of the city. So we picked up stories, we start talking to the cadets that went to the New York Military Academy with him. And we talked to one of his friends who was there, a fellow named Michael Squadron. And Michael Squadron was in his room one day and they were getting ready to go for graduation photos. It was in the fall and they were getting ready for the yearbook, and Donald walks into his room and sees Michael’s jacket has more medals on it than Donald’s. And Donald asked if he could wear Michael’s jacket for the class photo.

So over and over, almost page by page, we start to see the Donald Trump form that we know today. We start to see all these incidents that are very familiar to people today. And he was doing it when he was 12, 15, 16.

I’ve always thought that one of Trump’s superpowers is a lack of shame. He’s capable, in a way that no other politician is, of standing up on a stage and saying Two plus two equals five. Journalists will say, No, it’s four, and he’ll just look at them and say, You’re wrong, it’s five. That is not something anyone else is able to pull off. And as you demonstrated in this book, it’s something that he’s been doing since he was a kid at the swimming pool.

Craig: Just to get those first stories from people was incredible. We talked to another woman who lived across the street and he was throwing rocks in her window. This was the kid that we know today. These were the first signs of that.

The thing that really ends up saving Trump in the later phases of his career is The Apprentice. What was his financial situation at the time when Mark Burnett, the super-producer, came and pitched him on starring in this reality TV show?

Buettner: I would sum it up as stagnant and generally trending downward. He had a complete collapse around 1990. He had taken out almost $1 billion in loans that he couldn’t repay. The banks made him sell off a whole bunch of stuff. He put his casinos through bankruptcy, the Plaza Hotel, which he had bought, through bankruptcy, and he couldn’t really get loans after that to buy more big stuff.

So he was trying to buy little things. He bought land and tried to turn it into golf courses. He had mixed success at that and really hadn’t generated much profit. He had tried to put his name on some of other people’s projects because he was recognized as very good at bringing attention to things, obviously, but that hadn’t been a huge moneymaker. And his casinos were about to go into bankruptcy again, and he would have to come up with $50 million that year in order to keep any kind of stake in the casinos.

He was about to push his siblings into selling off their father’s empire, which he didn’t want to happen. The father didn’t want that to happen. So that’s where he was. The situation was dire and he needed cash.

And in 1995, this is one thing that you guys uncovered when you got all the tax documents, he had recorded more than $1 billion in losses over the last ten years. How big a loss is that in terms of someone with his wealth at the time? Was that devastating for him?

Buettner: I don’t think there is any context for that. We found a database that was a sampling of large tax filers. It was anonymized, but we were able to re-identify him because the numbers were so unique and so huge. There was nothing even close to that. And part of that is because he very aggressively wrote off some of the money he had borrowed as a personal loss to himself.

And we talked to accountants who said that may have been possible for a brief window of time, but probably wasn’t. And he was uniquely positioned to do that because of the amount of money he had borrowed and the staggering size of the failure. That was all personal, it wasn’t buried in a corporate balance sheet.

Craig: I think in one or two of those years, we found that he lost more money than any other individual taxpayer in America. This isn’t just like he lost a lot of money and there’s hundreds of others there. No. We couldn’t believe it when we went in and we found this. His losses were singular for like every individual taxpayer in America.

And then The Apprentice comes along. How did that come together?

Craig: So in 2002, he meets Mark Burnett at an event at Wollman Rink. Mark Burnett is the famous producer that did Survivor. And he was there filming a finale of Survivor. And they briefly meet, the event was at Woolman Rink and Donald Trump was there. And then a year later, Survivor was a red-hot hit, and Mark Burnett wanted to see if he could do it another way. He decides, okay, I want to do Survivor, but in the urban jungle. And for that, he needs a host of the show. Somebody who young kids would want to fight with and strive and connive in order to want to go work for that person.

Mark Burnett looked at a number of people. He thought maybe Jack Walsh would want to do it. Maybe Warren Buffett. Mark Burnett and his team came to the conclusion that they either weren’t great for TV or they were too busy. And then he remembered Donald Trump and he thought Donald Trump would have the charisma to do it. And I think probably genuinely thought Donald Trump was this hugely successful fellow.

So Mark Burnett approaches Donald Trump, and actually it’s an interesting story that maybe should have given Mark Burnett a clue that Donald Trump wasn’t as successful as he was claiming. In Mark Burnett’s telling of the story, he flies into New York, he’s coming in to pitch to Donald Trump, and he’s hoping to have a couple of weeks to get his stuff together. And so he calls Donald Trump wanting to set up that meeting for two weeks from that time, three weeks from the time. And he calls Donald Trump’s office and he says it’s Mark Burnett and he’s put right through to Donald Trump. Donald Trump was there and had enough time to immediately take the call. And he says, come on over to Trump Tower right now. And Mark Burnett is freaking out thinking, my God, I was going to have two weeks to refine the speech. He ends up an hour later in Donald Trump’s office. They have a meeting.

And according to Mark Burnett’s telling of it, they come to an agreement where Donald Trump is going to do the show. At that point, he was going to be the host for a year. But the important thing that they agreed upon at that moment, Donald Trump would be paid per show, but Mark Burnett and Donald Trump would split the product integration money that the show would generate. And what that is, when you think of product integration and you think of a Coke can or a bag of Doritos. Mark Burnett had used this on Survivor, but so far I think it was largely unrealized how much money you could make out of it. But they said, we’ll split the product integration money if we get any from the show. That became just hugely lucrative for Donald Trump. But that deal between Mark Burnett and Donald Trump came together quite quickly.

Because the contestants were selling products that ended up making them millions and millions per episode.

Craig: Once season 1 was a hit, it just took off. Like $3 or $4 million an episode, it was incredible.

Mark Burnett and his team were a little bit underwhelmed by Trump Tower when they first came to visit it. Could you tell us about that?

Buettner: It’s a pretty amazing moment. So these people had been filming in jungles and they had very well-trained eyes to find things that would evoke a certain emotion in the jungles. That was always fear, because the whole thing of Survivor was that people were facing life-threatening things, snakes and spiders. So they walk into Trump Tower thinking, now we’re going to need this central figure of the show, who’s going to be the prize of the show, someone who’s so wealthy and successful and knowledgeable that all these smart people will beat themselves to death to try to get a one-year internship.

Grovel at his feet for just the chance to work for him.

Buettner: And so they think when they walk in here, this is what they’re going to see. They’re just going to see wealth and prosperity and a humming, buzzing, thriving worldwide enterprise. And they step off the elevator and the first thing you notice is it stinks. Just smells bad. The carpet smells like it’s full of mold. And they look across the furniture and it’s all chipped and there’s nicks out of everything.

And they go into the Master of the Universe’s office expecting, again, this hub of worldwide activity. And there’s no computer. There are no blueprints. There’s no files there. There’s just piles, very orderly piles of newspaper clippings and magazine articles about one subject. Donald Trump.

So they realize they have this very huge bar to get over. The first is this guy is not what they’re going to bill him as. And so they’re going to have to invent that person. But they’re also going to have to invent a place that looks like a successful office place. So they hire someone to be a set designer and rent space from Donald Trump in one of the vacant floors of Trump Tower to build a boardroom and to build suites that would look like fancy places for the contestants.

So that’s step one of building that illusion. Step two is, and you guys have this incredible detail about the opening segment of The Apprentice, where there’s this aerial shot filming all of these properties and describing them as gems of the Trump Organization, when really they’re all in states of disrepair and on the verge of bankruptcy.

Craig: Trump Water is there. They’ve got one of the casinos and Seven Springs where he tried and was still failing to get a golf course. They’re one by one. They go through them as if they’re these crown jewels and they’re all losing money.

You also describe Trump as totally disengaged from the details and even the broad narrative of what’s going on in this TV show that he’s starring in. He would often fire totally the wrong person that producers wanted him to fire. You quote one member of the production team as saying, “Our job then was to reverse-engineer the show and to make him not look like a complete moron.” Again, myth-building about Donald Trump, making it seem like he’s this really good businessman, deal-maker, manager. What effect did that have, The Apprentice and its success, on creating this image of Donald Trump?

Buettner: There’s a good metric of that to start off with. There was a Gallup survey that was conducted about 18 months before the show that measured well-known people’s approval rating by the public. And Donald Trump, almost everyone knew who he was. It was like 98%. But the majority of people viewed him unfavorably based on all of his bankruptcies and his marriages and infidelities being in the paper. Eighteen months after the show, they did it again. And his approval rating was, I think, about 50% from the public. That was an amazing jump during a time where nothing had happened other than he had been on television every week looking like a very competent, thoughtful, precise businessman. And that really captures the power of this segment they created that they called Meet the Billionaire, and then repeating this every week, variations of that opened the show all the time and really reinvented his image, reinvented his finances as well. And that is an image of him that was locked in the public’s mind, his supporters’ minds, through to today.

Craig: We say it was the greatest political ad ever, a lot. We would talk about when we were reporting the book just how powerful that opening scene is. It’s played in different variations, but just the power of it.

Buettner: Even when all those things that they’re saying about those properties are not true. Like that thing is not doing well. He’s going to go into bankruptcy on that. You’re still like, well, this is really impressive, though. It’s really hard to fight that human impulse. And that’s part of the magic of Mark Burnett.

Not to mention, the money that he makes on The Apprentice. Funnily enough, the show is premised on this idea that he is already extraordinarily wealthy, that he’s a billionaire. But then he gets one of the big windfalls of his life on the basis of that fantasy. And it creates this lore about him that will end up being crucial for his 2016 run for president. So really, this turned his life around both financially and in creating this image.

Craig: It was like the second big windfall that he got. The first one was what he inherited from his father. And then this just extraordinary amount of money that he was able to make from The Apprentice. And it is really shocking because nobody really understood the mechanics of: you have a host, he’s paid whatever an episode, $50,000, $100,000 if he’s successful.

But that product integration deal that they struck was just so lucrative for Trump. If a company was paying 4 million and it went up to 5 million, we got a lot of financials for the show, we could see what each company was paying to get their product on the show, he would get half of that. And he didn’t have any overhead, he wasn’t paying for anything, he was just getting half of that. And when the producers would come up and talk to him about the company that week that was going to be on, his first question was pretty much always, well, how much are they paying? Because he was getting half of it.

It wasn’t just that though. From that, he got licensing deals that came because of The Apprentice. Those were worth hundreds of millions of dollars. And also, they got a cut if the contestants made a shirt or made a product that the company that was paying to be on the show actually sold. He would get a cut of that potentially. So there was just so much money coming from many directions.

Buettner: I think you also see the power of that reinvention in the licensing deals, because just before this, he had been trying to do this and they laughed him out of the office, literally. And during the show, he suggested to Pontiac, GM should make a car named after me. And the executive he was talking to for Pontiac thought he was joking, it was clear he wasn’t, but he looked into it. He made a joke and said, maybe we should call it the Trummer because GM makes the Hummer. But Trump didn’t laugh and said, here’s my card, look into it and call me. And the guy said, I looked into it, but there was no record of his name bringing success to anything so we didn’t do it.

But within a year of the show, companies were just lining up, including Phillips Van Heusen, Macy’s, all these very big national consumer brands, to give him money just to use the name, the value that had been created by the show.

You write in the book that we are in a world where “fame detached from any other marketable talent or skill” is a “highly compensated vocation.” Does that explain his success in your view?

Buettner: That’s complicated. His successes are really complicated.

But what’s the driver for it? Is he a marketer more than a businessman?

Craig: Yeah, that’s how I came to feel about it. You look at the fame and the money that it drew, just his name on something, his association with something would at least draw eyeballs if not sales.

And it’s a Potemkin village, because there’s not a lot underneath. It’s the idea that he’s a successful businessman. It’s not that he actually is one.

Craig: He also found some things he tried to sell, they failed. He was starting to put his name on anything, and I think it became damaging to him.

Buettner: Also I think if you look at it over time, it’s hard to not notice that there’s something unique about the way Americans attach the idea of expertise to somebody. And we touch on this in the book, that if you’re wealthy or you appear to be wealthy, he has signposts of wealth, even when there’s all kinds of financial turmoil going on, we assign credibility and capability and intelligence to that person. And we’re hesitant to challenge what appears to be their expertise. And I think he’s benefited from that his entire life. And I think that’s why he fights so hard to look wealthy, because that means, in his mind and to a lot of people in America, that he’s great at whatever he says he’s great at. And that’s been central to his place in the culture for a lot of decades.

Craig: We found early in his career, we would send the clips back and forth because we were just laughing, he all of a sudden becomes famous early in his career effectively, and all these TV personalities are asking him his views on world affairs and stuff he knows nothing about. But they attached, because he had money, they thought, he’s smart, he has thoughts on all of this, when in fact, it was ridiculous.

What role do you think the media played in all of this? You write in the book about how the media didn’t really look into his claims. The Wall Street Journal reported that he had sold off all of his stock before a stock market crash without looking into it. Another outlet reported that he was a billionaire in the 1980s. What role do you think the media played in helping him make this myth?

Craig: I think that’s an easy question to look at that today. There’s two things. One is I don’t think back then everybody thought that guy was going to be in the White House, and he was more an entertainer than he was a businessman. He did make the pages of The Wall Street Journal. He had businesses. But I don’t think he was taken seriously, like he was running a publicly traded company like Goldman Sachs or Morgan Stanley or Exxon.

So I think he, at the time, got away with a lot because he was within a privately-held company, it was small. And I think people saw him more as a celebrity than they did a serious businessman at the time. And I think that the real work in terms of what people like Russ and I were doing started when he ran for the presidency. But that was a different era then, and that’s why we went back and looked at it all.

Buettner: There’s a certain way we cover people who are trying to do something that comes with great responsibility. Donald Trump had never done that. He was never taking over a public corporation. He was never really an important part of our public affairs. But he was fun. And he answered the phone. He was always accessible. He said, look at my helicopter. Look at my gold-plated apartment. Look at my latest wife, girlfriend, mistress, whatever. And that’s the way he was covered.

So when he says, I’m a multibillionaire and I have all this stuff all over the world, there’s really not a reason to go in and check that. He’s not applying for a loan from you. He wasn’t yet running for president. He’s just colorful.

Trump sent a cease and desist letter after an excerpt of your book was published in The New York Times. What happened there?

Buettner: So it’s a letter. It will proceed in whatever legal course it’s going to proceed in.

He has sued you before. He just had to pay, a couple months ago, all of your legal fees.

Craig: For the paper, right. But it’s also important to know we did try and engage him during the book with questions, a lot of questions, and we hoped that he would engage, but he didn’t. We wanted him to. But we also were lucky with Donald Trump, he’s been living out loud most of his life. So there is an incredible, rich trove of information and documents and interviews to go back to. So in that sense, we were lucky. But he didn’t engage us during the book.

His campaign communications director, Steven Cheung, issued a comment on your book. He called it, “A desperate attempt to interfere in the election, lies, incoherent nonsense, either belongs in the discount bargain bin in the fiction section of the bookstore, or it should be repurposed as toilet paper.”

Buettner: It’s unclear how he feels about it.

I don’t want to assume anything, but I don’t think that they’ve read the book.

Buettner: It’s quite certain he had not at that point. But I think they would say that no matter what they saw in it. And I think what that really means and what we always see is that this notion of Donald Trump is really central to his identity. And Steven knows it’s going to make the boss angry and he’s going to react accordingly.

This is still something that he’s very sensitive about.

Craig: It came up at the presidential debate. Kamala Harris brought it up. He keeps going back to the “I’m a self-made guy.” And that his father was this outer-borough builder. It’s just so deep inside of him. She was baiting him, she brought it up and succeeded.

And he would deny the inheritance, which is a hard thing for him to deny because there are documents.

Buettner: As you said, he has no shame. And I totally agree. I’ve thought that about him for ten years now. That is one of the remarkable things about him. I think that there’s two sides of that. One is that we as a society, again, have a difficult time saying to the face of someone who appears to be rich and successful, you’re lying to me. And he has no problem lying to your face even when you know he’s lying to your face. And you put those two things together and he creates a fantasy world that he inhabits.

Craig: And he believes in the power of the lie. If the lie is said over and over and over, it eventually becomes fact. People will start to think it’s true.

How much do we know about his financial situation now? We’ve got the Truth Social SPAC, but the numbers are down 70%. Yet his stake is still valued at almost $2 billion. What do we know about how he’s doing now?

Buettner: We don’t have a perfect window, really for any particular time. But we know what the trend lines were and they’re not good. After The Apprentice wellspring, he invested that money in himself instead of the stock market and tried to create the impression, again, that he was a successful businessman by building a tower in Chicago, that he secretly declared worthless on his tax returns it was such a failure, by buying some golf courses in the United Kingdom that we know are all losing money, and he was having to put money into them from his fame money, by renovating the old [Washington, D.C.,] post office into a hotel, he was having to put $7 to $10 million a year in there to keep it open until he sold it off. So those were not good numbers.

And he was taking that Apprentice money, which in 2011, that and the licensing money was $50 million in one year, and putting a lot into those things. Well, all The Apprentice money went away, almost all the licensing money went away when he declared his candidacy with the way he described Mexican immigrants, the rest of it evaporated. So that was all gone. A hotel that had paid him $30 million in Hawaii broke their relationships off with him. So the trend lines were all down and he hasn’t really replaced that with anything.

And you see him now, it’s a much more smaller market thing, trying to monetize, I called it “Martyr Inc.” in a recent story — trying to monetize his political persecution. And that’s really what is at the center of Truth Social, is people believing they’re persecuted because he’s persecuted and we’ve got to prop him up. That is the one thing that could save him. But if he starts to sell, when that window opens up in a couple of days, it’s going to drive the stock price down immediately. He wouldn’t even be able to unload all his shares before it’s driven down.

It sounds like he’s back to merchandise, really. Hats and mugs and books.

Craig: And crypto. The other thing to remember, we don’t know how it’s going to play out, but he’s facing these regulatory fines with the New York attorney general in excess of $400 million. We don’t know what’s going to happen on appeal, but if that goes through, he’s going to have to write a check for that. So I think you’re seeing a lot of headwinds that he’s got now.

This is a tough question, but you have exposed an extraordinary amount of private information, about Trump’s financial situation. A lot of potential fraud and an extraordinary amount of dishonesty. Why do you think it hasn’t had an impact on public opinion about him? And is it frustrating to see him still potentially being re-elected president, having done such an enormous amount of work exposing this kind of stuff?

Craig: I think it probably has had an impact. I think, though, when you look at Donald Trump, I think people just take away from him what they want. And they’re willing to believe some of that story, but also maybe they see it, he’s a fraudster, but he’s good on whatever issue you care about. And so I think that his voters, they’re either not going to believe it or they’re going to look the other way. That’s how I process it. They see he’s had all this legal trouble. He recently had the criminal case in New York. And either they’re going to think he’s being wrongly persecuted or they’re just going to say, well, I like him because he’s good on this.

Buettner: I don’t think I’ve ever started looking into something or finished something with the idea that it’s going to create some specific outrage. Of course you do it because it’s fascinating and it feels important and you hope other people will follow you along. And it’s when it’s really hard, it makes it all the more interesting. So it did that. And this just turns into this great epic drama of a particular life in America, a particular family over the course of a century. It tells us, as we say in the book, as much about us as a country as it does about him. And I think that in part gets at what you’re talking about, is that’s part of the magic story of his life, why do all these bad things happen and then why do all these lucky things happen? But yet he still remains firmly embedded with a particular image in our culture among a large number of people.

Craig: This is just a great story. That’s what I really loved about it and loved about the book. It happened to be Donald Trump, but it was just this epic story of a man, of a family, and everything that bound them or didn’t. A really incredible tale.

The title of the book is Lucky Loser. That’s about the fact that this man has been incredibly lucky with these breaks throughout his life and was born into extraordinary wealth and still managed at many turns to lose money and bankrupt businesses, etc. Yet at the end of the day, Trump won. He was the 45th president of the United States. What do you think that says about America?

Buettner: Wow, that’s a big question. Well done. That’s really big question.

If anyone wants to get the full answer, it’s in the book.

Buettner: Look, the presidency isn’t really a meritocracy. We want to think we’re picking the absolute best person out of 330 million people, but we’re really not. It’s a mix. The first thing most candidates strive for is name recognition. Donald Trump’s had name recognition since he was 24 years old. So it’s not really a test of who’s the best.

But it does bring to light a lot of things that are not great about our whole economic system and our whole political system. We’re not as great as we want to think we are at vetting someone’s potential before they walk into that office. Donald Trump was still an enigma to most people, I think, when he first walked into the White House. And we learned after the fact that what we saw there, and I hope through this book, is who we would have seen if we had been able to do all that spadework in that tight window in 2016.

Craig: I don’t think people knew what’s in our book. I think for the American people, when they went to vote, they saw the person that Mark Burnett had created. And I think there was a segment of society that saw him in New York and knew the tabloid guy and the infidelities and the bankruptcies. But I think a lot of people thought that was well in his past. And he was the successful person that Mark Burnett had created. But I agree, the presidency isn’t a meritocracy at all.

Buettner: I’d like to add that I think your question was smarter than our answer.

Susanne Craig and Russ Buettner. The book is called Lucky Loser: How Donald Trump Squandered His Father’s Fortune and Created the Illusion of Success. Thanks so much for coming on Press Club.

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