Trump AKA the Lucky Loser

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1:32Hello, I'm Anthony Scaramucci, and this is Open Book, where I talk with some of the brightest minds out there about everything surrounding the written word, from authors and historians to figures in entertainment, neuroscientists, political activists, and of course, Wall Street. Sorry, I can't resist. Before we get into today's episode, if you haven't already, please hit follow or subscribe wherever you get your podcasts and leave us a review. We all love a review, even the bad ones. I want to hear the parts you're enjoying or how we can do better. You know, I can roll with the punches, so let me know.

2:06Anyways, let's get to it.

2:16Lucky Loser. What a great title from the New York Times investigative reporters Russell Buettner and Suzanne Craig. And what's even greater is that it's describing Donald Trump. Russell and Suzanne's book reveals the true accounting and myths of Trump and his money, what he had, what he lost, and what he has left. We delve into everything from Trump's time at the military academy to the influence of his father, Fred Trump, their complex relationship, and his ultimate obsession with wealth and status. Let's get into it.

2:56I'd like to take a second to recommend my friend Andy Ostroy's great podcast, The Back Room. Every episode is a fun, incredibly honest take on our society and the political situation, along with some brilliant guests. I've been honored to join Andy on the show, and you know anywhere that accepts me with no filter deserves a shout out.

3:22okay a big delight for me joining us now is russell buettner and suzanne craig they are both world-famous investigative reporters for the new york times the title of the book is lucky loser what great alliteration i just hope no one ever calls me the lucky loser but the title of this book, Is Lucky Loser? How Donald Trump Squandered His Father's Fortune and Created the Illusion of Success. And boy, are we living with the yoke of all that now, guys. So I want to go to the first question and sort of these are for both of you and we can switch back and forth. But since 2016, you've both been focused on the personal finances of Mr.

4:02Trump. Susan, specifically, I've seen some of your interviews. I think you've got some of this information from the Trump family articulating how much money he was given, what he did to divide out and conquer his other relatives to keep a lot of that money, and then what he did with it. But let's go to both of you with this central question. Why did you take this on? So let's start with you, Suzanne, and then I'll ask Russ the same question. Why did you get involved with this? Well, it started because an editor just asked me if I could look into Donald Trump and his money, and that was back in 2016.

4:35I was actually, I'd been covering Governor Cuomo in Albany. I just arrived at City Hall. I was going to be the bureau chief for the New York Times covering then Mayor Bill de Blasio. I was super excited about it. I'd been in the seat three weeks and I get a call from the Metro editor and he says, hey, can you just come out for a few weeks? Donald Trump just announced he's running for president. Nobody really thought he was going to be in very long. And I was told you'll be back at City Hall in a few months, I never went back. And we started just writing on his finances back then. Very little was known about his finances.

5:08There'd been this discussion in New York and the tabloids. He was this billionaire and all the noise that went around with that. But we really didn't know much about how much he was worth, even in some cases, what he owned. It was a privately held company and it was sort of just shrouded in mystery and mainly his myth-making about it, which was false. So Russ and I started writing on it. We each did, you know, kind of separate stories prior to the election. And then six weeks before the election, I went to check my mailbox one Friday afternoon. And I found in my mailbox, it was incredible, a manila envelope addressed to me.

5:45It had three pages of what looked like Donald Trump's 1995 tax returns. And when I went to the line about how much we assume he had losses. It looked like he had a billion dollars in accumulated losses in 1995. We couldn't believe it. We worked around the clock to try and confirm that. We ended up getting it confirmed from an on-the-record-source accountant that had signed the document. And from there, we just kept working, you know, just trying to uncover more information. And we started looking at how much Donald Trump had inherited from his father, Fred Trump. And that story, we just started digging into property records and calling people.

6:27And that story that ran in 2018, we discovered Donald Trump, he'd long claimed that he had inherited almost nothing from his father. In fact, he'd inherited hundreds of millions of dollars from his father, and it was enhanced through tax fraud. That was the story. You mentioned some Trump family members helped us with us. Mary Trump had given some really important documents that helped us get to that story. Then we just kept digging and we got it later on. Another source gave us 20 plus years of Donald Trump's personal and corporate tax returns that led to a series of stories in 2020. And there were other stories along the way.

7:05So it was really an organic journalism effort that just kind of kept going and now has ended up with this book. So this is the heart of Mr. Trump. If there's an Achilles heel for Mr. Trump, it's this book. And so, Russ, let me go to that. I mean, he believes his political power comes from the Celebrity Apprentice, as you guys pointed out in The New York Times Sunday article this weekend, and that it comes from his wealth. He is a genius, multi-billionaire. He's the only person that the Forbes 400 people say tries to boost his record. A lot of people are trying to get themselves off that list. he's trying to get himself higher up on it.

7:44And so this strikes right at the heart of him. And so Russ, you know, why give yourself this agita? You know, you seem like a nice guy and probably have a nice family and everything. Why would you want to be antagonized by him? Because I'm sure he's antagonizing. Yeah, the world is full of unpleasant people and we don't pick our subjects usually based on how fun they are. But this one is particularly unique because, As you know, he pops onto the political scene in 2016 with nothing much behind him but years as a television celebrity. And this business record that he says shows he's an incredible genius, that he's a multi-billionaire, and that he's promising he can now do the same thing for the country that he had done for his businesses.

8:27But this was a very small, privately held family company. To try to do the usual vetting that we and the public would do of a candidate for president was very difficult because those records are not there. Even compared to, say, Mitt Romney, you could look back at the funds he'd been involved with and tell something about that. And most people running for office are government officials who have a long public track record. Mitt divulged his tax returns, though, right? All of these. First thing. And Trump went out of his way to hide all that. So that, to investigative reporters, is just like a magnet.

9:00Come to me, right? And everything that we found out just sort of upended another element of his myth of who he was. And when we get to the end of it, we've done sort of three large stories over a five-year period. But there was so much more to tell in just connecting all that and trying to figure out where it was that he became the person that he was, where it was that American culture sort of enabled him to tell these lies about what he was doing and still be credible. There were changes in the media ecosystem in those years that were a big role. And so it just felt like as a long narrative exploring sort of an American century in the Trump family, it really had weight and helped us get to understand where we had gotten to.

9:42So, I mean, the title of your book is awesome. I mean, I love the alliteration and I applaud you guys for the title, but the title I was thinking of when I closed your book was Unchecked Bully. And throughout his life, he's an unchecked bully. And this book is providing the checks on a lot of things that have gone on. And I want to go right to the adolescent Trump. You guys have new interviews. You've went to his former classmates and friends, as well as some details about his high school years at New York Military Academy. The lore is that his father found him recalcitrant and found him to be very difficult.

10:16So he sent him to Military Academy for grooming, but he was unruly at the academy and was shirking some of his duties yet continued to rise in the ranks. So tell us what you learned in these new interviews about this young man, Donald Trump. Russ, do you want to start that one? Sure. It's an interesting thing. There's a split between, as you would see throughout his life, between sort of the way he portrayed himself and then the realities of the situation. So he gets there and it's a military hierarchy, but it's not really a military operation. Of course, these are young kids. And their main thing is wearing uniforms, marching, playing sports, making their beds in a certain way, cleaning the bathrooms.

10:57And there's this hierarchy of authority that develops. There's some adults that set the overall temperature of the place. But then most of that enforcement of those things falls to senior cadets, to high school kids who are managing the people below them. And Donald Trump right away seems to recognize that he wants to be in those upper ranks of people. and he tries to do that, but he has a problem. He doesn't actually manage the people that he's associated with. In fact, one of his captains beats up a young cadet and they decide he's just been too inattentive to managing the sort of power structure there.

11:33So they move him off. A lot of the cadets there thought he would be pushed out of leadership altogether, but they put him in a supply role and he was sort of at that level, but not really part of the overall kind of hierarchy of authority. And then this like weird thing happens as they're taking the pictures for the yearbook in his senior year. He wants that authority still. He's still craving or that sort of the honor of that. He wants the credibility of having done really well there. So he has this friend, Michael Skadron, who has all these medals from various things he's accomplished during his years there.

12:08And Donald asks to borrow his dress uniform so he can sit in the yearbook photo with all of those medals. And that sort of gets to the split between what he wanted to be, how he presented himself, and then the reality of the situation. But it also speaks to his general mendacity, right? So he's able to, you know, when you play golf with him, it's known as the Donald Trump foot wedge, where the foot comes out and kicks the ball everywhere. and or you know i have buddies of mine play gobbledum and he he races up he takes their ball off the fairway throws it in the rough kicks his ball 50 60 yards down the fairway and so so he's been doing that his whole life that's why i say he's an unchecked bully he's unchecked he's allowed to do this there's something about the american culture that is allowing for this you know before i read your book i saw trump as logan roy and i saw him as the patriarch in secession when i finished your book, I actually now see him as Kendall Roy.

13:04I didn't realize that distinction, but Logan Roy is Fred Trump. Wow. Okay. And he's actually Kendall Roy. And there's this weird relationship. There's a combination of loyalty, but also manipulation in that relationship based on your reporting, based on the way you describe it. And so tell us about Fred Trump and the power that he had over Donald Trump. Well, I hadn't thought about it that way, but it's a really interesting story. Donald Trump looms so large in our life, but when you actually go back and you look at it, it was Fred Trump who really was the power. Well, you taught me that, Suzanne.

13:37I didn't get that on my own. Yeah, I just hadn't thought about that Lilligan cat because there's a lot of succession. Yeah, I saw him as the patriarch, but he's really not. The oldest son dies of alcoholism. He becomes the heir apparent to the oldest son, and he has all of this, but he's been hit hard by the dad. And so there's a lot of that Kendall Roy insecurity in Donald Trump. There's so much of it. And when you see what happened, there was another brother, Fred Sr., Mary Trump's father. And it's just a tragic story. Initially, not surprisingly, he was the eldest son. There was a time when Fred saw him as the heir apparent.

14:17And we talked to people who went to school with Freddie, the young son, the eldest son. And it sounded like he planned to go into the family business at one point, but he also had other interests. And he just became inadequate to Fred, the father. And it just, it never worked. He quickly fell away. He ended up dying of alcoholism when he was in his early 40s. And Fred Trump needed an heir. He wasn't going to pick his daughters. You know, they were just, that was not a path for them. They even went to different schools than the boys. So Fred Trump put his chips on Donald. And it's really fascinating when you think about that, because whatever you think about Fred Trump, he was a good businessman and he didn't believe in debt.

15:01He didn't believe in giving personal obligations to banks. He believed that cash was king. There were so many things that he, you know, just the disciplines of business that he had that Donald Trump broke. You know, famously the debt Donald Trump would take on just all of it. And no matter what, we never saw a moment where Fred Trump, once he had made the decision that Donald Trump was his man to take over the company, that he wavered in that decision. So it is fascinating. And we've thought a lot about it. It's quite surprising. And we talked to people who knew real estate moguls at that time, and they knew the sons.

15:38There's a lot of instances in New York where the son would be coming up the ranks to take over the father's company. And those men, for the most part, seem to be really hard on their sons. And one of the people we talked to in the books that he'd run into Fred Trump and Fred Trump would just be like, isn't my Donnie great? You know, and, you know, Donald was basically a black hole for Fred Trump's money, but he just never seemed to question it. So there's manipulation though there too, right? I mean, there, he's manipulating his son. Tell us a little bit about that. Sometimes I think it's the other way around that Donald was manipulating his father.

16:10I think a bit of both though, maybe actually, now that I think about it. Do you agree with my Kendall Roy analogy or no? I mean, I got that out of your book, actually. So that was one comment. But the second comment, I felt like the father wanted Trump to be a certain way and he was going to push and shove him. And the money was incentivization to get him to do things a certain way. Do I have that wrong? Or maybe I have that wrong. It's hard to say, like, I don't know if we can get into the relationship that much. I'm sure that was a component of it as well. Well, I think what one thing that struck us as interesting and surprised us was the degree to which Sue said, once Freddie, the older son, is out of the picture and Donald Trump emerges, Donald Trump is in many ways the polar opposite of Fred Trump.

16:50He brags about doing projects that he never does. Fred Trump never did that. He doesn't pay attention to the bottom line. And so he runs huge deficits. Fred Trump never did that in his entire career. And he doesn't pay his bills. Fred Trump never did not pay a bill. And he was incredibly braggadocious. But Fred Trump embraced those things and he would defend them. And by the time around 1984, when Trump Tower is starting to open up, there's this weird scene where they're having the capping ceremony at the top of the tower. And Fred is there. He's now 80 years old. But suddenly he sounds like Donald Trump.

17:27Somebody asks him how sales are going. And he said, stupendous, fabulous, best ever in the history of New York City. He had never spoken like that. We had watched interviews with him. He was very dry and precise when he talked about things, even when he was in trouble and irritated by the line of questioning. But all of a sudden, he's like a chain of superlatives, just like his son. And even as Donald Trump lied about his father's accomplishment to elevate his own, saying my father was small time, my father built little projects in Brooklyn and Queens, not acknowledging those projects would be worth a billion dollars in the course of Fred Trump's lifetime.

17:59Fred Trump didn't object to that. He said, yes, he surpassed me in every way possible. So it is a really weird and dynamic relationship. And I'm sure what you're saying was a major component of it as well. So I asked one of my, you know, I got my career started at Goldman Sachs after I left law school. And I asked my, one of my mentors, who's now 80, he would insist on being nameless because he'll choke me if I put his name out there. But I asked him about this because he knew Trump and he knew Fred. Okay. And remember I started in the real estate department at Goldman. And so I, and I, and I met the first time I met Donald Trump, I was an associate at Goldman Sachs.

18:37And this is obviously Trump would have never remembered that meeting because it was, I was probably in my late twenties at the time. And obviously he was famous. I wasn't, but, but my old mentor said that he got away with the big lie because people actually want to believe the big lie. And, and so So when he said things like, I borrowed in 1975 a small amount of money from my dad and I converted it into billions of dollars, it sounds good. And so people are like, OK, with it. When the story comes out that you accurately report and you've got the tax returns that he lost billions of dollars and he inherited$400 million from his dad, if you just put it in the S &P 500, he would have done way better.

19:17that he's literally squandered the treasure that his father gave him and he blocked his family members, some of his family members from getting it. It's not a good story, Suzanne. So what ends up happening is people don't believe it. They like hearing the other story. There are people at his MAGA rallies that would read your book and say, fake news, not believable. Donald Trump is a mega genius, a startup billionaire. What do you say about that? What's your reaction to what I'm And do you believe anything I'm saying or do you think? Well, I think people love a hardscrabble story. And I think Donald Trump actually was born into wealth and he was probably upset that he was robbed of the opportunity to tell a hardscrabble story.

19:59So he's made one up. I mean, it's really it really is something I think people do want to believe it. And then I also think we have to remember the time that Donald Trump sort of came of age in New York. It was a celebrity. He was known more as a celebrity, as a businessman. You know, I worked at The Wall Street Journal. I covered Goldman Sachs for years. Those were publicly traded companies that had to report in every quarter. Donald Trump reported into Donald Trump. We could never really get inside it, but his company also wasn't consequential in a way that big publicly traded companies like Goldman were.

20:31When I covered Goldman, it was a full-time job at the Wall Street Journal, just covering Goldman Sachs. And so he sort of was on this celebrity kind of specter in New York. And so I just think there were some reporters who did incredible work on him. Neil Barsky is one at the Wall Street Journal when Donald Trump had the casinos and there was publicly traded companies involved. And he did puncture some of the lies. But I think that, you know, just it still amazes me. One of the things about the book that he was able to rise for 20 some years with, you know, first of all, appropriating his father's wealth as his own and then just lying about his wealth.

21:08And it was just repeated over and over and over by the New York Times, by 60 Minutes. It almost defied belief when you actually just started looking at some of the basic facts back then that we could find, but it just kept going. Well, your colleague Maggie Haberman in the book The Con Man, she writes about the headline, The Best Sex Ever. It was a total manifestation of his mind, and he was able to get it into the front page of the New York Post. That was never said by his second wife. Okay, let me go to this. I'm going to ask you this, Russ. Obsessed. He's absolutely obsessed and possessed about status.

21:43And rich people in my lifetime, and again, maybe you guys have had a different experience, but super rich people are not obsessed about that. They just aren't, you know, and so, you know, striving rich people are, but not really rich people. Like when Trump says, I'm really, really rich. First thing I think of is Shakespeare. Doubt does protest too much, you know, meaning he's not really, really rich. So why, Russ? Why the obsession? What do you think it is? It's an excellent question. I mean, I think it's part of the definition you see in narcissism. I'm not a psychologist, but you have to believe that you're superior to everybody else in the world, right?

22:20And that seems to have been the main mission of his life is to portray himself as superior. And that's a benchmark that he used. I think in our book, Fred Trump is a great sort of juxtaposition for that again, because he lived a modest life. He built a house for his family in the early 1950s, and they lived the rest of his life in that house and never took extra vacations. Went to Florida, never took a cruise, bought his wife a mink coat once a year, every once in a while, bought her a Rolls Royce every couple of years. But that was it. Donald Trump immediately becomes obsessed with symbols of status and wealth as a symbol of his excellence.

22:57And I think that's part of what the book has to say about how we got here and America, American culture's sort of role in his rise is that the qualities that we imbue and people who show signs of wealth, right? He was right, it turns out, to want it because people did assume he was excellent. People did assume he must be really good at whatever he says he's good at because look, he's got a jet, right? That's all you need. And that has sustained itself. And you combine that, America's sort of acceptance of excellence when there's signs of money and not wanting to challenge those people, not feeling comfortable to say, I'm as smart as them to question what they're doing with somebody who, as you said, is built on mendacity, who has no shame about lying right to your face, even when he knows that you know it's not true at that very second, right?

23:47You could have the object in your hand. He'll tell you this object is green. Right. And you're staring at the object, but he's telling you it's green. And then you start to be gaslit, but he's like, OK. You're making such a good point, too, about, you know, people who are actually rich don't want the attention. And I remember in 2016, I started doing some stories on his planes. One of them was one of the big 757. Kind of how crappy it is. And I got on this because somebody who I covered on Wall Street, one of the CEOs who's quite wealthy, I was talking to him one day on the phone and Trump was running and he said, you should really look at that plane because it's an awful condition.

24:24He goes, I wouldn't step on it. Like people in New York sort of saw through it. He was buying the accoutrements of wealth and often didn't keep them up. And I think people who actually had money, they don't want the attention and they saw through. I mean, that plane is loud. The plane is a gas guzzler, but the size of the plane, he's trying to impress the hoi polloi with that plane, you know, and he's already made the decision begrudgingly that the ultra rich will never really accept him. You know, the Posners will, but the super rich, you know, whether they're in Palm Beach up here in New York or you pick them are disgusted by him.