TERRY GROSS, HOST:

This is FRESH AIR. I'm Terry Gross. Donald Trump's claims to being one of the wealthiest, most successful and brilliant businessmen was created with smoke and mirrors using his father's wealth, media-created myths, lots of enormous loans, instances of tax fraud, along with false claims and unkept promises. The details are laid out in a new book by my guests Susanne Craig and Russ Buettner, two New York Times reporters who have been investigating Trump's business practices and finances ever since he campaigned for the presidency in 2016. One of their early clues came from several pages of Trump's tax documents that were leaked to Susanne Craig in a manila envelope she found in her New York Times mailbox.

Craig and Buettner won a Pulitzer Prize for their reporting. Now they've written a new book called "Lucky Loser: How Donald Trump Squandered His Father's Fortune And Created The Illusion Of Success."

Susanne Craig and Russ Buettner, welcome to FRESH AIR. I want to start by saying that we're recording this on Monday. And whatever we discuss about Donald Trump's finances doesn't change the fact that the second attempted assassination of Donald Trump and all the threats of violence surrounding this election is deeply upsetting, deeply disturbing. I'm wondering if this is an awkward moment for you to be talking about the book.

RUSS BUETTNER: Well, anytime there's an attempt on someone's life, it does have a way of making everything else seem inconsequential. But we are still propelling ourselves towards a presidential election, when the voters are going to have to decide, make some very hard decisions. And so we have to handle all those things at the same time.

GROSS: I also want to mention that you just got a cease and desist letter from one of Trump's lawyers regarding an excerpt of the book, or an adaptation of a chapter of the book, about "The Apprentice" that was published in The New York Times. So what does that mean and how are you handling that?

SUSANNE CRAIG: You know, it's always, I think, you know, worth noting when you get a legal letter. And I think for now, you know, we're going to proceed and talk about the book. We stand by the book. I understand from his point of view the truth can sometimes hurt, and he litigates when things like this happen. But we're really proud of the book, every word in it, and we stand by it. We're excited about it. So we're going to move forward to talk about the book and to talk about our work, and also to keep reporting on Donald Trump at The New York Times.

GROSS: What is the state of Trump's finances now? He's lost a lot of licensing deals. There's businesses that he lost since he announced for president in 2016, and also since "The Apprentice" was canceled after he announced. So where does he stand now financially?

BUETTNER: That is always a very difficult thing to ascertain. We have a very thorough record of his tax returns and some financial records through 2018. More of that came out afterwards. As near as we can tell, the big difference is that - the two things that have insulated him from sort of the repercussions of the way he tends to run businesses were his inheritance from his father and the money he received for being on "The Apprentice" and all the licensing deals that came from that that you mentioned. Those two big pots of money, that's close to $1 billion in today's money. That mostly is not going to be available to him, and he has several businesses that lose money.

So we think we're going to see continued contraction by Donald Trump. He sold the money-losing Old Post Office hotel, or his lease to operate it. He sold his lease to operate a golf course in the Bronx. He sold several apartments that he owned that were worth quite a bit. So it looks to us like it's going to continue to shrink, and that these judgments - if they hold, especially - could really create an existential threat to his finances.

GROSS: And when he sells businesses, he has to use a lot of that money to pay off loans, right?

BUETTNER: That's right. He has to use a lot of it to pay off loans. He also encounters depreciation recapture tax, which is a weird tax that's basically an accounting thing but causes a real expense, and a capital gains tax if he makes any money on it. So like in the Old Post Office case, it looked like he had quite a windfall. But it looks like also all that money went to paying the commitments on the property.

GROSS: And that's the post office in Washington, D.C., that he converted into a hotel?

BUETTNER: Correct.

CRAIG: Well, you've also seen Donald Trump move into, I think, these licensing deals. Those are very familiar to him because he did a lot of them during "The Apprentice." But now they look a little bit like the politics of grievance. He's selling sneakers. He's selling Bibles. And those are licensing deals. They're certainly not going to bring in a huge amount of money, but I think we will see more of that going forward. And he's also got a social media platform. It's called Truth Social. We don't know how much that'll ultimately bring him, and the stock isn't doing well now.

But I think we're going to see, going forward, him moving into that sort of - more licensing businesses. He's also got some licensing businesses overseas with the Saudis, and that's the sort of thing he's moving into now. It's certainly not the sort of money we saw both from the money he inherited and the money he got from "The Apprentice." But that's the sort of stuff that's now bubbling up.

GROSS: So a lot of the book is about, you know, deals on hotels and, you know, buildings like Trump Tower and casino. Some of the book is about how the media created the image of Trump as this wildly successful businessman. And I want to talk about that a little bit because that's part of what got him elected as president in 2016, was this image that you kind of undo in your book. So let's start with 1982, when he was listed on Forbes' first list of the 400 wealthiest Americans. Based on what? What were his finances like and what did he claim to be?

BUETTNER: I mean, that's one of the great mysteries. That's one of the things that requires constant untangling about Donald Trump, is this is a very small, privately owned family operation. And that was based almost entirely on Forbes looking at some of the properties that the family owned that was his father's business at the time and trying to assign some value to that. And really, when you go back and look at it, it was based on things that Donald Trump told Forbes reporters. And that's how he got there. And within a short period of time, he added - he told Forbes that he had taken over the company and he had complete control of its finances and its operation. And that was not true either.

GROSS: Right, so part of what he was claiming as his was really his father's wealth.

CRAIG: I think, Terry, what I found to be one of the most surprising parts of the book was just how successfully and how long it went on that Donald Trump lied about his wealth and that he was able to do that without anybody - there was a few reporters who did question him. But it started in the 1970s, just when he was in his 20s. There was a New York Times article that ran in the early 1970s that claimed at a very young age that his wealth was more than $200 million. He had just, you know, taken that - that was his father's wealth - and said it was his own. And that went on for decades and you see through serious publications, and also even on "60 Minutes." They were calling him a billionaire with no evidence.

You know, he was seen as a celebrity back then, and there was no real examination of his wealth. It was privately held and so you couldn't really get under it, but the willingness of the media to enable that really fueled his rise in that period. And he was getting on shows like "Lifestyles Of The Rich And Famous." The host, Robin Leach, was there. And Robin Leach was putting him on because Donald Trump appeared to look rich. Donald Trump had bought the accoutrements of wealth and the helicopters and the yachts. And that all fueled, I think, the person and the image that was created, you know, that fueled his rise to the White House.

GROSS: Well, let me reintroduce you here. If you're just joining us, my guests are Susanne Craig and Russ Buettner, Pulitzer Prize-winning reporters for The New York Times. Their new book is called "Lucky Loser: How Donald Trump Squandered His Father's Fortune And Created The Illusion Of Success." We'll be right back. This is FRESH AIR.

(SOUNDBITE OF DAN AUERBACH SONG, "HEARTBROKEN, IN DISREPAIR")

GROSS: This is FRESH AIR. Let's get back to my interview with Russ Buettner and Susanne Craig, authors of the new book "Lucky Loser: How Donald Trump Squandered His Father's Fortune And Created The Illusion Of Success." They've been investigating Trump's finances ever since he campaigned for president in 2016.

You have a fascinating chapter in the book that was excerpted in The New York Times about "The Apprentice" and how that show enhanced his image of, you know, most successful, brilliant businessmen but also gave him so many licensing deals that made him more money than a lot of his properties did. So let's talk about "The Apprentice" and why it's so important. First of all, how was he chosen as the host over Richard Branson and Jack Welch, who was the head of General Motors, and Warren Buffett?

CRAIG: Those are some serious names that you mentioned in there - you know, legitimate businessmen and very wealthy. And Mark Burnett, who is the producer of "The Apprentice," looked at...

GROSS: ...And created "Survivor."

CRAIG: And created "Survivor." And, you know, that's an important thing to mention actually because he was just a leader in the genre of reality TV. And when "The Apprentice" was pitched, he was coming off "Survivor." That was a story about competing in the jungle, and he wanted to do another show that was about the urban jungle, and he needed a host for that. And he looked at a number of wealthy men, the ones that you mentioned. And it was concluded they either didn't have the charisma or the time to do it. And he had met Donald Trump in 2002.

Just - and then a year later, when he was looking at doing this - "The Apprentice," survival in the urban jungle - he approached Donald Trump and asked if he'd be interested. And Donald Trump was very interested. And he had - I think, most importantly, he had the charisma to do it. His businesses were - actually, a lot of them were in trouble at that time, and Mark Burnett came into his life at a very fortuitous time. And we couldn't have known it at the time, but, you know, in the end, he ended up making hundreds of millions of dollars from "The Apprentice" and the licensing deals that followed.

GROSS: Before "The Apprentice" started shooting, producers went to the floor of Trump Tower, where Trump's offices were. Describe what they saw on that floor.

BUETTNER: Well, the first thing they described to us was the smell. They stepped off the elevator, and everything had this musty carpet odor. It just made an immediate impression that this was not the center of a thriving, hugely prosperous, successful organization. And then as they look around - these are people who are trained to notice details. They had just come back from years in the jungles, like, taking films of spiders and snakes to, like, evoke danger in viewers. And they started noticing - while they're looking for signs of wealth, they notice that all the furniture seems to be chipped. There are all these marks out of it. Everything seems very dated back to when the building was opened in the mid-1980s.

They looked at Donald Trump's desk, and they saw no sign of, like, a thriving operation. They just saw stacks of newspaper clippings that were just all about him. And so right away, they had the impression that they had a challenging job to try to make this person look like an icon of business success, the sort of person that a bunch of contestants would snipe and backbite against each other to try to win an apprenticeship with.

GROSS: When you were talking to one of the producers of "The Apprentice" about this, he said, our job was to make Trump look legitimate, to make him look like there was something behind it, even though we pretty much all knew that there wasn't, but that was our job. What are some of the first things they did to create his image as a successful businessman in addition to having to create a fake boardroom?

BUETTNER: It's an excellent question. They expended great resources to basically make a commercial to Donald Trump's exceptionalism. They spent weeks filming little snippets, the goal of which to make - was to make him look like the king of New York and to craft this sort of comeback story from his mid-, early 1990s collapse. So they filmed him standing on top of Trump Tower.

There's this incredible episode where a helicopter's circling in to take a picture of him up there, and his hair flies up, and he's asking the producers if it's OK. They took sequences in the properties all around the Northeast to make it look like he was sort of the king of everything. And they had him narrate this that - saying that New York can be a really tough place. But if you make it big, you can really make it big here - or huge here. And while they're doing that, they're showing things - businesses that are actually not doing well but that he owns. So there was already this sort of built-in tension between the truth and reality in that.

But that three-minute segment that they called "Meet The Billionaire" was really one of the most amazing things at reinventing Donald Trump's image, and you saw that in Gallup polls just over the first 18 months of the show. He went from everybody knowing him but most people not having a favorable view of him to having - for the first time they were taking those polls, a majority of the people they surveyed had a favorable view of Donald Trump. In fact, 18 months after they started airing that series, he received the higher - highest favorability rating in a Gallup survey he's ever received to this day.

CRAIG: The power of repetition of that opening scene in "The Apprentice" can never be underestimated. And in some ways, I think it's the greatest political commercial of all time. And I think that that image then fueled his rise to the White House. I think a majority of Americans believed what they saw, that Donald Trump was a successful billionaire in New York who had come back from adversity and had built an empire from nothing because over and over, it was repeated, year after year, on that show.

GROSS: You report that during "The Apprentice," the producers thought that sometimes Trump fired the wrong person. Can you tell that story?

BUETTNER: It would create these incredible moments in the control booth, where they would all be expecting one person who had underperformed all week to be fired, and all of a sudden, Trump would fire somebody else. And then they'd have to go back through the hundreds of hours of tape they had shot that week on the contest for the week and make that one person look like they were messing up throughout the week so Donald Trump's decision would make sense. But it was also television magic. There was just joy in the booth that even if they had to go back and refilm it, it was unpredictable. It added this dramatic tension to the show that became really central to what they were - wound up trying to do.

CRAIG: One of the producers we talked to about this particular issue said, when we saw that happen, we knew we had a show.

GROSS: Part of the deal is that Trump was supposed to evenly split income from product integration. That's product placement.

CRAIG: It is product placement. If you remember back - and a lot of people have seen shows like "Survivor," maybe "The Apprentice" - and you imagine the contestants on the show competing for a prize, it may be a bag of Doritos. Or, you know, there could be a soda can on there that has a corporate name on it. The companies that own those products or those brands - they're paying to be on the show.

And Mark Burnett had come in to "The Apprentice" having known that model. He hadn't so far made much money off of it, but when he negotiated "The Apprentice" with NBC, he said, you guys can have the commercials. They were making a lot of money on the commercials. He said, but I want the product placement money. So if a corporation wants to come on, if a toothpaste company wants to come on the show and the contestants on the show can compete to make a ad for that toothpaste company and they want to pay $2 million for that, Mark Burnett would retain that money.

In the case of "The Apprentice," Mark Burnett and Donald Trump would split those checks. So if a company came on and paid 2 million and they wanted their product on "The Apprentice," Donald Trump would get a check for a million, and Mark Burnett would get a check for a million dollars. It was an incredibly lucrative deal after the first season of "The Apprentice" when those deals started rolling in.

And Russ and I obtained the financial information for "The Apprentice," a lot of financial detail. And we just couldn't believe how much companies were paying, just clamoring to get on that show. Some companies paid up to 4, $5 million to be on it, and every time they cut a check, Donald Trump would get half of it.

GROSS: He had up sponsors for side deals of his own. Can you tell the Levi's story?

CRAIG: Sure (laughter). That's a wonderful story. So this was, I think, during the second season of "The Apprentice," and Levi's had sponsored an episode. And Donald Trump was on set, and he had got Melania to put on a pair of Levi's jeans and said to the CEO of Levi's, doesn't she look great in these jeans? And the CEO said, she looks fabulous in them. And so Donald Trump seized on this moment and had a discussion with one of his producers, and they agreed that Melania would do a little side deal with Levi's where she would model the jeans and she would get paid $50,000 to do that. And the producer that Donald Trump talked to - Donald Trump promised him 5% of the deal. And so Melania did the - did it, got the check for $50,000. She went down and did a photo shoot at Levi's down in SoHo in New York.

Then not long after, Donald Trump calls the producer who organized this forum, and he said, come on up to the apartment to the producer. And producer was all excited. So he hustled up to the apartment, and Donald Trump opened the door. And Donald Trump invited him in, and Donald Trump yelled up to Melania to come down the stairs. And, of course, the producer is thinking he's going to get his check, his cut of this $50,000 deal. And Melania starts coming down the stairs, and she's holding a golf putter that's got a felt cover on it and hands it to Donald. And Donald says, Kevin, thank you very much. That was the producer. Here's something for your efforts on that, and he signed it.

And the producer just was looking at Donald thinking, where is my check, and should I say something? He's pretty upset about this. He just thought to himself, is this really worth it? Am I going to upset the talent? So he just smiled, and he took the golf putter. And he went back down to the set, and that was the end of it.

GROSS: He didn't want to do anything that would upset the program.

CRAIG: No. And that's what we heard over and over as Donald Trump - we heard about a number of side deals that he cut where he would cut Mark Burnett out of money, and there were ones much larger than that that went into the millions of dollars. And, you know, we kept saying, well, why didn't you say something to him? Like, Mark Burnett was due half of that. There was so much money coming in, but half of it should have gone to Mark. And they just did not, at that point, want to upset the talent because Donald Trump could walk. And so they let these side deals go time and time again.

GROSS: Well, there's a lot more I want to talk with you about, but first, we have to take another short break. If you're just joining us, my guests are Susanne Craig and Russ Buettner, Pulitzer Prize-winning reporters at The New York Times. Their new book is called "Lucky Loser: How Donald Trump Squandered His Father's Fortune And Created The Illusion Of Success." We'll be right back after a short break. I'm Terry Gross, and this is FRESH AIR.

(SOUNDBITE OF BALTIC HOUSE ORCHESTRA'S "THE APPRENTICE (MAIN TITLE THEME)")

GROSS: This is FRESH AIR. I'm Terry Gross. Let's get back to my interview with New York Times reporters Russ Buettner and Susanne Craig. They've been investigating Donald Trump's finances ever since he became the Republican presidential candidate in 2016. They won a Pulitzer Prize for their reporting, and now they've written a new book called "Lucky Loser: How Donald Trump Squandered His Father's Fortune And Created The Illusion Of Success."

So all of the licensing deals that Trump benefited from during the run of "The Apprentice," he invested a lot of that in businesses, in - sometimes in new businesses, and those businesses lost money (laughter). So he lost of the - a lot of the money that he made. What were some of those businesses?

BUETTNER: Well, one of the biggest ones was a tower in Chicago. It was a combination of residential and hotel units. It had a commercial space on the ground floor - took him years to build that. And one of the most interesting things about that that we uncovered in the course of this reporting was that while he was saying publicly this was a huge success - this massive tower on the river - on the shore of the Chicago River - he had privately declared the building to be completely worthless to him on his tax returns. He had borrowed far more money on it than what he generated in sales. The retail and commercial portion on the ground floor still remains vacant, I believe, almost 15 years after it was completed, and it was a big money-loser for him, and he had a hard time holding onto it.

Another one was the renovation of the Old Post Office in Washington, D.C., into a very fancy hotel. He made a beautiful project. But even when he bid on it initially, other hotel companies said, he's going to pay too much for this. He's never going to make money on it. And then after he opened it to much fanfare - right? - during his 2016 campaign, it immediately started clocking losses. And we saw on his tax returns that every year, he had to pump in another $7 to $10 million to just - to keep the thing going. And eventually, he was forced to sell that. He also built or purchased several golf courses in the United Kingdom during that period of time, all of which turned to be significant money-losers, and that remains kind of a problem on his balance sheet from what we can tell.

GROSS: When Trump announced his candidacy in 2016 after coming down the escalator at Trump Tower, and he said Mexico was, quote, "sending people that have lots of problems. They're bringing drugs. They're bringing crime. They're rapists. And some, I assume, are good people." You read that the NBC executives were appalled, and licensing agreements started to dry up. Can you give us some examples of the reaction to that announcement that he was running for the presidency?

CRAIG: Yeah, the reaction was fast and furious, both from NBC, the network, and also from a number of the companies that he had licensing agreements with. I remember talking to Paul Telegdy, one of the senior executives at NBC, about it. And he immediately called Trump, and they had quite an argument about it. I think at one point, Donald Trump called him a p**** for not, you know, wanting to just stick with the show and stick with Trump in the moment. And NBC pretty much immediately cut ties with him.

And there were a number of organizations - of companies that had branding agreements with him. And I remember during the reporting talking to several of them. And one in particular stands out in my mind, and it was the people who were making the Trump perfume that was at Macy's, and they immediately moved to get just boxes of the perfume off the shelves. They did. They were successful. It was shipped back to a warehouse and then put on a gray market. Some of it, I understand, ended up in those perfume stores that you see, I think, you know, on the - some of the avenues in America. But it was immediately removed from the shelves and sold or given away into gray markets.

GROSS: And this perfume had been sold for $60 a bottle.

CRAIG: It had been, and within a day or two, it was taken off the shelves. I actually spoke to somebody whose job it was to take it off the shelves, and...

GROSS: Oh, really?

CRAIG: ...They moved quickly to get it out of the store. They just did not want to be associated with him after that. He lost so much money in licensing deals because of the comments that he made that day.

GROSS: So Trump had his own brands that were licensed, like Trump Steaks, Trump water, the Trump perfume. Did he get out of licensing his own products after so many licensing deals fell through?

BUETTNER: It took him a long time. He was quite stubborn in trying to market his name, and he's still trying today. But there is an interesting arc to it, where early in "The Apprentice," he'd been trying for several years to get new products licensed, where he would just get money for his name being on something. Even during "The Apprentice," there's one episode where he asked the head of Pontiac marketing to create a car named Trump. The executive looked into it and decided there had never been a successful product with Trump's name on it, and there was no reason to.

But within a year after that, companies are literally lining up - and some of them quite shady and inexperienced - to try to get him to do that. And that was an incredible windfall for him. And he also, as a part of that, tried to put his name on products that he was distributing sort of himself - Trump Ice, Trump Vodka, Trump Steaks. But all of that sort of faded away. He did a lot of reputational harm to himself by not vetting those companies. So you see Trump University blowing up and becoming a big problem for him. It's called a fraud by everyone who was involved in it.

And so then towards the end of that arc, that money is really starting to dry up when he runs for president. He had been making as much as $50 million a year some years between "The Apprentice" and the licensing deals. And by the time he's running, it's dropping down into the single digit of millions - still significant - but it just completely dries up. And since then, we've seen him try to reinvent sort of small ball versions of that that he's marketing as part of his campaign - like we mentioned, the Bible, tennis shoes with his initials on them. And none of that has really got the broad market appeal of what he enjoyed during the heyday of his licensing business.

GROSS: It's time for another break. If you're just joining us, my guests are Susanne Craig and Russ Buettner, Pulitzer Prize-winning reporters for The New York Times. Their new book is called "Lucky Loser: How Donald Trump Squandered His Father's Fortune And Created The Illusion Of Success." We'll be right back. This is FRESH AIR.

(SOUNDBITE OF AHMAD JAMAL'S "THE LINE")

GROSS: This is FRESH AIR. Let's get back to my interview with Russ Buettner and Susanne Craig, authors of the new book "Lucky Loser: How Donald Trump Squandered His Father's Fortune And Created The Illusion Of Success." They've been investigating Trump's finances ever since he campaigned for president in 2016.

Let's talk about Trump Tower. You know, one of the things I found really interesting about the Trump Tower section of your book is that there was a fire on the 28th floor during construction, and they had to rush to complete the building and make it schedule. When residents started to move in, a lot of them decided to redecorate. Why were they so...

CRAIG: (Laughter).

GROSS: ...Concerned and disappointed by the floors and the appliances in Trump Tower?

CRAIG: He had put in lower-quality products in order to save money during the process. So he was selling these as luxury apartment buildings. And they were luxury units. But when people started moving in, they couldn't believe the poor quality of the construction of things or, you know, the appliances, the fridges, the stoves - that sort of thing. So a lot of them had to be - got renovated after the tenants had actually moved in, the owners had moved in.

GROSS: There's fake marble.

CRAIG: Yeah.

GROSS: Parquet wood tile floors.

CRAIG: Yeah.

GROSS: Not luxurious.

CRAIG: No, and it's interesting because the people moving in found that. And then Donald Trump, of course, has a famous triplex in the building that he still owns today. And he had hired a very famous, a very serious designer that his wife had at the time, Ivana, to decorate it. It took years to do. It was beautifully done. It was written up in magazines to much fanfare when they finally moved in. And Donald Trump was unhappy about it, so he ordered another renovation of it. And he ended up hiring a designer who was known for doing high roller suites at casinos.

And that's how we end up with the apartment - the very gold-plated apartment that we have today. It was actually a second redo. And we talked to a lot of people involved in that renovation. They were very surprised that Donald Trump didn't like the initial renovation because it was so beautiful. But he wanted to hew to his taste. And he actually hired, you know, this fellow who was doing high roller suites at casinos.

GROSS: So we're talking about the 1980s here because Trump Tower was finished, I think, in 1982.

BUETTNER: I think it was - I want to say '84.

GROSS: OK, but it's in that vicinity.

BUETTNER: Yeah.

GROSS: And so it's right after that that he starts this, like, acquisition and building spree. And those things end up losing money. Does Television City fit into that period?

BUETTNER: Absolutely. To me...

GROSS: Would you describe what it is - because I'd never even heard of Television City, and why should I? It never existed.

BUETTNER: (Laughter).

GROSS: He never got to actually, you know, create it. But what was it supposed to be? And what did he say about how, you know, innovative and important this was going to be?

BUETTNER: That was such a major turning point in his life. Had been trying for 10 years to acquire the rights, or hold onto the rights, to develop this large swath of undeveloped land on the west side of Manhattan. It was about 70 acres. There were just old railyards there and weeds. And he finally got control of it for a second time, after great expense, in the mid-'80s. And he announced the most absurdly huge project that I think we've ever seen in Manhattan. It was going to be the world's tallest building, a dozen or so residential towers all around that, retail space. Just a massive project.

And he asserted that the reason for that was - the sort of anchor tenant would be that NBC was going to leave Manhattan, and that would be a horrible loss. And so he would create a studio for them within this new city in a city he was building, and he would call it Television City. And he made this announcement at this amazing press conference in December of 1985, I believe. And it got just national coverage. You've really never seen anything like the attention that this got. It was teased the night before by "60 Minutes." And everything was taken as fact that he was going to do this, and he immediately ran into problems.

So he ultimately had to change it to Trump City. He downsized it three or four times. This went on for eight or nine years. All the while, he's paying tens of millions of dollars - some year, hundreds of millions of dollars - to hang onto this property that's undeveloped. But it was really a major turning point in his life and this idea that we flesh out in the book that he came to believe - that anything he could get money for, he could do, and that he could get over any sort of regulatory hurdle that was raised to him. And it was a lesson in proving the fallacy of that belief.

GROSS: So you said Television City ran into problems. What kind of problems did Trump run into?

BUETTNER: Well, first, they were almost all of his own creation. First was just the sheer size of it. Everybody warned him that this project was too big. The prior person who controlled the site had not been able to get a smaller project approved because it was too big. And Trump increased that, I believe, by about a third and then thought he would just run over the city. And Ed Koch, who was the mayor at the time, had a different idea about that. The local community, the west side of - Upper West Side of Manhattan, which is a very activist area, really didn't like the idea of this gigantic behemoth of buildings towering over their charming brownstones.

So he immediately ran into problems with that, and he got into a horrible sort of public insult match with Mayor Ed Koch. Mayor Koch called him little piggy. He called Mayor Ed Koch - this will sound familiar - stupid, an idiot, a loser, a bunch of just very personal insults, suggesting that he was doing a horrible job running New York City. And that he should be - he tried to get Mayor Koch run out of office. So he ran into a whole host of problems that can haunt any sort of oversized real estate development. And his response to that would seem very familiar to people that are familiar with how he operated as a president, that he would just try to insult and berate people into compliance. And it didn't work.

GROSS: Did anything get built from that project?

BUETTNER: Eventually it did, but not by him. After he downsized the project several times, he did win in the early '90s approval for the zoning. By then, his finances were so bad he couldn't get a loan to do anything there, and so he had to give away control of the project to a consortium based in Hong Kong. They, unknown at the time, had complete control of it. They made him a 30% partner, but they had all decisions over finances, over what would be built, over who would be hired to build it. They were going to run construction. He would just be a passive partner in that. And his primary focus was, again, that his name would be in certain places on the project. And so it got built, and he sort of presented himself as having built this big project on the west side, which people see from the highways on the west side of Manhattan now. He really had been a passive - sort of along for the ride in that project.

GROSS: And what was it called?

BUETTNER: It was called Trump Place for a while. There was a street named that. Some of the buildings bore his name, but many of the buildings since, which are co-ops, cooperative apartment buildings that are owned by the actual tenants or the owners there, have chosen to remove his name from the building.

GROSS: Let me reintroduce you again. My guests are Susanne Craig and Russ Buettner. They're Pulitzer Prize-winning reporters at the New York Times. Their new book is called "Lucky Loser: How Donald Trump Squandered His Father's Fortune And Created The Illusion Of Success." We'll be right back. This is FRESH AIR.

(SOUNDBITE OF YO LA TENGO'S "WEATHER SHY")

GROSS: This is FRESH AIR. Let's get back to my interview with Russ Buettner and Susanne Craig, authors of the new book "Lucky Loser: How Donald Trump Squandered His Father's Fortune And Created The Illusion Of Success." They've been investigating Trump's finances ever since he campaigned for President in 2016.

Trump used so much of his father's money and claimed some of his father's fortune as being his own. And he had a lot of, like, failures, lost a lot of money. How much of the failure, how much of the bragging, saying that his father's money was actually Donald Trump's money - how much of that did Fred Trump, Donald Trump's father, live to see? And I know Fred Trump died in his 90s, and he had dementia by the time he died. So how much of Trump's failures and distortions did Fred Trump get to see before his own cognitive abilities were clouded by dementia?

CRAIG: Fred Trump died in 1999. And when you actually think about what Fred Trump did get to see, he got to see some of I think what people would consider Donald Trump's, first of all, biggest successes. He saw the Grand Hyatt and Trump Tower being built. But he also lived through the debacle of the casinos, also the airlines. There was a lot of the bad that Fred Trump got to see as well.

And it's interesting. The casinos - Fred Trump actually, at one point, had a lawyer. He had sent a lawyer to one of the casinos with money to try and actually help bail his son out. But when I think about the relationship between Fred and Donald - in, you know, the first part of the book, we look at first Fred Trump and then the relationship between Fred and Donald because it is so formative. Fred Trump - in our reporting, we would see that he believed in careful planning. He believed in financial forecasting. He had hesitancy to take on large debts. He never gave personal guarantees.

And Donald Trump - as he started running the family business or being involved in the family business when he was in his 20s, he broke the fundamental rules of business that had been just central to Fred Trump's success. And despite that, you never saw Fred Trump waver. We have never gotten a hint of that. And it's interesting. There's a scene in the book where we talked to somebody who knew a number of the real estate tycoons at this time, and he knew their sons. And he always remembered how hard those men were on their sons and how demanding they were of their sons. And they said they never saw that in Fred Trump. They would run into Fred, and Fred would say, how about my Donny? He was so proud of them all the time.

And when we think about why that happened, you know, you can never know. It's hard to get into the relationship - family relationships - a father, a son, a mother and a daughter. But I think Fred Trump wanted an heir. He wanted one very badly. And I think when we look at the family and - you know, he - Donald Trump had a brother, Fred Jr., who was actually Fred Sr.'s namesake, and the eldest son.

When that didn't work out, Fred Jr. had other interests. You know, he liked to fly and just wanted to be in the family business but also wanted to do other things. And I think his dad just cast him aside at some point and didn't want him. And Fred Jr. ended up drinking and died in his early 40s. Fred Trump was then left with one heir, and it was Donald Trump. But that decision was made early on, when Donald was 18 or 19. And I think once Fred Trump had made the decision that Donald was his heir, there was no going back, and he was going to support him at any cost.

GROSS: In the acknowledgments of your book, you mention a lot of names. I assume some of those names are sources. Were you concerned about the possibility of some of the people mentioned in the acknowledgments being attacked under the assumption that some of those people might have been sources and Trump would object to them being sources? And when Trump is critical of someone, they're likely to be attacked on social media or perhaps doxxed or perhaps have people show up at their home to intimidate them.

CRAIG: You know, it's interesting. In the acknowledgments, we do name both a number of sources that we talked to and experts who helped us out. In the case of the sources, we made sure with them that they were OK that we named them and we wanted to acknowledge them.

One of them I think a lot of people know is Mary Trump. She is the niece of Donald Trump and has been a very outspoken critic of him. In 2017, I met her. And at that point, nobody knew that those discussions were going on, but she gave us a lot of information about her family, particularly her grandfather's finances - Fred Trump's finances that helped us build that story that ran in 2018. And we made sure that she was comfortable that we would name her, and she's actually written a book where she has talked about her relationship with us. There's another case of a fellow who came forward and gave us a lot of corporate and personal tax return information. He unfortunately is in jail, but we wanted to acknowledge him and to thank him for his help in getting us that information, and we also made sure with him that he was OK that he was mentioned.

GROSS: You write that the Trump era has presented unique challenges for journalists. What challenges has it presented for you?

BUETTNER: Well, I think the first one is just that - what do you do when someone emerges at about 70 years old and says, I should be president because I've been a success in business my entire life? Now I'm going to do for the country what I've done for my businesses. In the case of a privately held business like this, what is the reality check for that? That's an incredibly difficult process. There are no public records. There's nothing disclosed about the performance of his properties. So how do you help the public vet what that person says - that they're a success in business and that means they can run the country? That is the biggest frustration that we faced.

And then I think the second part of that is the period that we live in, that the truth doesn't necessarily break through all the noise on a daily basis, that Donald Trump's assertions on a daily basis are picked up by certain media outlets who take them as the earnest truth and then go from there, expand upon them, amplify them. And so things don't always break through the noise, and that is at the center of the American experience, I think - is the idea that we make the best decision as a society over time based on the truth.

CRAIG: And sometimes the truth just takes a long time to get to. Russ and I have spent 10 years on this. We spent full time two or three years writing the book. And in the meantime, you know, Donald Trump says something, and it's amplified around the world in seconds. It's tough.

GROSS: There was a long period when Trump would call people or do publicity for himself under the name John Barron. It was an alias that he used so that people wouldn't think he was doing his own publicity or beating his own drum, although he was. And I don't know if you can speak to this at all, but, you know, he named his son Barron. And Barron was his alias or pseudonym or, you know, whatever name you wanted to call it. It was John Barron. Do you have any idea why he named his son or he and his wife named his son after his own pseudonym?

BUETTNER: That is a puzzle for the ages.

(LAUGHTER)

BUETTNER: You know, one of the interesting parts of our reporting in this is we were always paying attention to his use of that name, and we discovered that he started using it as soon as he left college and started working for his father. His father had always taken out classified ads. They always had the house phone number, sometimes the office phone number. All of a sudden, the classified ads had the name of contact of Mr. John Barron. And the only thing that had changed was Donald Trump had started working there. And so, yes, how do you go through your entire adult life using this one name to hide your true identity and then decide to give that to your child? It is really a confusing proposition.

GROSS: Russ Buettner, Susanne Craig, thank you so much for your reporting, and thank you so much for being a guest on our show.

BUETTNER: Thank you for having us.

CRAIG: Thank you.

GROSS: Susanne Craig and Russ Buettner are the authors of the new book "Lucky Loser." Tomorrow on FRESH AIR, our guest will be TV journalist Connie Chung. In a new memoir, she details her climb to the top of her male-dominated field, her love of hard news and her nearly 40-year marriage to tabloid talk show host Maury Povich. She also talks about the state of TV news today. I hope you'll join us. To keep up with what's on the show and get highlights of our interviews, follow us on Instagram at @NPRFreshAir.

FRESH AIR's executive producer is Danny Miller. Our technical director and engineer is Audrey Bentham. Our interviews and reviews are produced and edited by Phyllis Myers, Ann Marie Baldonado, Sam Briger, Lauren Krenzel, Therese Madden, Monique Nazareth, Thea Chaloner, Susan Nyakundi, Joel Wolfram. And we're very happy to welcome Anna Bauman to our production team. Hey, Anna. Welcome to FRESH AIR.

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GROSS: Our digital media producers are Molly Seavy-Nesper and Sabrina Siewert. Roberta Shorrock directs the show. Our co-host is Tonya Mosley. I'm Terry Gross.

(SOUNDBITE OF CRAIG DAVIS' "BATTLE OF THE BALCONY JIVE") Transcript provided by NPR, Copyright NPR.

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