Gabriel Sherman's "The Apprentice" – Trump, Cohn, and a Legacy of Monstrous Deceit
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Hey folks, today on the Lincoln Project Podcast, we have a rare spoiler alert. Our guest today is Gabriel Sherman, the author of the phenomenal new movie, The Apprentice, which is about Donald Trump's younger years and his relationship with Roy Cohn, who shaped Trump's path to power and Trump's dark, twisted, and frankly, evil soul. But if you have not seen the movie yet, be advised, this contains heavy spoilers. And I mean a lot of heavy spoilers. If not,

Let's go. Your task will not be an easy one. Your enemy is well-trained, well-equipped, and battle-hardened. There is not a liberal America and a conservative America. United States of America. Good night and good luck. Hey, folks. Welcome back to the Lincoln Project Podcast. Our guest today is Gabriel Sherman. He is the author of the tremendous new film, The Apprentice. The Apprentice.

Yes? Hello, this is Donald Trump from Mr. Cohen. Thank you so much. Donald who? One, two, three, four! Roy Cohn, nice to meet you. The Roy Cohn? You're brutal. Guilty as charged. I didn't always win. There's rules. The first rule is attack, attack, attack. It's going to be the finest building in the city. Maybe the country. In the world.

Rule two, admit nothing, deny everything. There's never been anything like this, at this magnitude, this quality. Ooh, cheese balls over here. What are you doing? You want one? No, it looks totally disgusting. Cheese balls. Rule three, no matter what happens, you claim victory and never admit defeat. You have to be willing to do anything to anyone to win.

You have a big ass. You gotta work on that. Your face looks like an orange. Attack, attack, attack. Deny everything. Admit nothing. Never admit defeat. What if you lost your fortune today? Well, then maybe I'll run for president. I don't know. I say if you're indicted, you're invited. Yeah!

It is a history and a story of Donald Trump and his relationship with Roy Cohn. Many of you are too young to remember Roy Cohn. Hell, I'm too young to remember Roy Cohn. But it's a fascinating lesson in history. I want to welcome Gabriel to the show today. Gabriel, talk to me about what inspired you to write The Apprentice and how your sort of revelations about Trump's character developed as you wrote this book.

Well, thanks, Rick, for having me. I'm a political journalist in addition to being a screenwriter. And this movie really owes its origin to my coverage of the 2016 presidential campaign. I wrote, I covered the Trump campaign for, at the time, New York Magazine. And I was struck by something people told me while I was covering the campaign. You know, Trump was, he was such a shock to the American political system. You know, nobody had heard somebody, you know, speak.

basically with such demagoguery before and just the name calling the politics of personal destruction. And I was struck by things that people like Roger Stone told me, which is they would say things like, you know, he sounds a lot like Roy Cohn in these in these speeches or he's just using the lessons Roy Cohn taught him. And it just came to me one day. It was shortly into the Trump presidency, the spring of 2017. I thought,

that's the movie, the relationship between the master Roy Cohn and his apprentice, Donald Trump. You know, it's funny. I think that Roy Cohn

is an underappreciated aspect of politics beyond just Trump. But you caught in this, that dynamic of those echoes that came through even today, the exaggerations, the lying, the setting off a new controversy to get out of an old controversy. Talk to us about how he and Cohn first intersected.

Well, the movie begins in 1973 when Donald Trump meets Roy Cohn at an exclusive New York City nightclub. Donald Trump at the time was in his late 20s and he was unhappily a rent collector for his father's Brooklyn and Queens real estate company. And the Trump family was being sued by the Justice Department for housing discrimination,

Right. Donald's father was a notorious racist and was sued for he was sued for refusing to rent to black tenants. And so the Trump family was being pressured by their lawyer to just settle the suit. And Donald Trump meets Roy Cohn at this nightclub and tells him about the lawsuit. And Roy Cohn says, don't settle, just sue the government, file a countersuit, create a counter narrative.

And that really clicked with Donald. The Trump family hired Cohn and they ended up basically winning the lawsuit. They settled for no financial fine and admitted no wrongdoing. And from there, Roy took Donald under his wing and opened the gates of power to New York society and taught him his three rules for politics, which we see every single day.

on the campaign trail. And those rules are, number one, attack, attack, attack. Number two, admit nothing, deny everything. And rule number three, never admit defeat, always claim victory. And you can basically boil down Donald Trump's entire political playbook to those three. That through line is absolutely vivid in any analysis of Trump today. Anytime you look at him, watch him, you know that that's where

the origin story of all this, this, of his tactics comes from. So as, so he meets Cone and, and Cone starts to shape his career. But this is also a story about how, what kind of a miserable person Donald Trump is. He's never been this, the, the, the character he plays to the public. He's never been as confident or as, as, as brash as he plays, you know, to the camera. It,

It's always, there's always like an under uncertainty about this guy. And is it, is, is this a story about his family as well? Like the upbringing of this guy had this absolutely nightmare family. Yeah.

Yeah, no, that's that's a great point, Rick. You know, the the movie begins in 1973, but obviously we see the after effects of Donald Trump's childhood growing up with an abusive father, Fred Trump, and an alcoholic older brother, Freddie. And really what this this movie shows is that, you know, Donald Trump was kind of searching for an identity. You know, when he meets Cohn, he's very awkward.

He's insecure. You know, in this this character, you know, it's obviously I want to stress this film is based on real events, but it is a drama. It is art.

But I based my early impressions on young Donald Trump. There's this interview I recommend your listeners go watch. It's on YouTube, and it's Donald Trump's first national television interview from 1980. It's with the TV personality Rona Barrett. And you see in this video how different he is today. He's soft-spoken. He's trying to be charming. He's a little bit stiff and awkward. And that, for me, was like the starting point of who Donald Trump was.

But after 15 years of being mentored by Roy Cohn, he then develops into this egomaniacal personality where, you know, it's all this sort of media myth of the of the dealmaking businessman. Right. And Cohn is a very dark figure in American politics. And and the darkest, the darkest, arguably one of the darkest figures in our in our entire political history. No question. And so.

I think Jeremy Strong in this captures him in a really kind of chilling way. This guy was almost reptilian in his desire to be in control. Yeah. I mean, obviously you can't play, you know, armchair psychologist, but, you know, clearly Roy Cohn was a sociopath. You know, he, he really, you know, practiced the politics, as I said, of personal destruction. He used

extortion and blackmail to pressure people to do what he wants. He was famously, you know, a closeted, he was gay, but he was closeted and he actually persecuted, you know, other gay, gay government officials. And he also basically taught Donald that there is no line, that basically the only line is whatever it takes to win. And I think that

stayed with Trump. And, you know, Roy Cohn was a lawyer. There's this amazing quote about Roy Cohn that he was a lawyer who had contempt for the law. And I think Donald Trump is a politician who has contempt for the institutions of American politics. No question. No question. This is the sound of your ride home with dad after he caught you vaping. Awkward, isn't it?

Most vapes contain seriously addictive levels of nicotine and disappointment. Know the real cost of vapes. Brought to you by the FDA. In this film, you see the sort of early relationship stuff that touches on his ego, like the liposuction, the hair transplants, all that stuff.

Is Donald's physical vanity still, to this day, his Achilles heel? Because I've always heard from people around him that that is the one thing that will set him off if he looks bad on camera, if the hair is wrong, if the suit doesn't look right. This clownish affect, though. But it really strikes me that that's one of the things that no one's really ever gotten to him on, even though he looks...

at all times. Yeah. No, I think you really, you're onto something. You know, the movie is, it works on many levels, but in some ways when I, when I wrote it, I imagined it, you know, it's partly a Frankenstein story where Roy Cohn's the scientist and he creates the monster, but it's also a little bit of a Pygmalion story. You know, Roy Cohn was always permatanned. Roy Cohn had, you know, excessive plastic surgery and,

There is a similarity of a vanity between Roy Cohn and Trump. And also, I think by the end of the film, you know, the visual metaphor of Trump having a scalp reduction surgery and having liposuction, you know, it's the visual metaphor of the monster is finally being created. And I think, you know, what I hope the movie does, because

Because it's not, you know, from the first, you know, frame of the film, it's not a political hit job. This to me, I wrote it as a character study because, you know, all of us have lived through the Trump years and just on a basic human level.

how does a person like this get created? And I wanted to try to write a film that would dramatize that subtle transformation from, you know, an ambitious, aggressive asshole into a megalomaniac. One of the things that captured it to me was

That moment where Sebastian Stan is, he rings the buzzer at Roy Cohn's apartment. And it's such a great little piece of acting. He's so tentative, like, Mr. Mr. Cohn, it's it's Donald Trump. And I just found that to be like, I thought that was going to get under his skin, too, because, you know, Trump has sold himself, you know, certainly to his MAGA followers, but even the Republican Party as this, you know,

strong man, you know, defiant leader. And I think seeing him insecure and nervous is such a punctures that that myth in a way that I don't think, you know, he he he I don't think he likes to pretend that that version of himself ever existed. He wants to think that he wants his followers to think he came out of the womb as this fully formed strong man. And this is clearly an identity that he has found.

Yeah, I think that's right. The idea that he was created in some way, I think, is probably pretty offensive to him. So they have tried to stop this film. They certainly went at it and tried to push back against its release. Talk to us a little bit of how that's worked out for them. Yeah, I mean, that's a whole, my friends joke that that's like a movie inside of a movie. Yeah, no, it's been a saga. The movie comes out tomorrow, Friday, October 11th.

Um, but for months this summer, it looked like the movie was never going to be released. Um, we had our world premiere at the Cannes film festival at the end of May and Trump's campaign, you know, without even seeing the film, you know, released this scorched earth statement, you know, following Roy Cohn's playbook, they went on the attack. Um, they called it, you know, malicious disinformation, foreign election interference, um, and a whole other bunch of, um, bullshit. But

you know, the, the, the legal threats had the intended effect of, um, basically making every major Hollywood studio, um, run away from this movie and be afraid to, to pick it up. So we were without a distributor, without any way to get this movie into either theaters or onto a streamer. Um, and on top of that, we had a financier. Um, our main, our main investor is the son-in-law of the Republican billionaire, Dan Snyder. Uh, uh,

former owner of the Washington Redskins, then Commanders. Dan Snyder hated the movie. His son-in-law ended up hating the movie. And so they were fighting us. They didn't want the movie released. So we had to raise $7 million from investors to first buy him out and then find a small distributor who had the guts to take it on. So we were fighting really this multi-front battle to get the film released.

And it had its North American premiere in August at the Telluride Film Festival. And I remember my wife and I booked our tickets to go, not even knowing if the film was going to be legally allowed to be shown. And at the 11th hour, the lawyers made a deal and we got, you know, we got the control of the movie. And now it's free to be released nationwide.

And, you know, there's been a lot of coverage in the media about the struggle of this movie to be released. So I'm really trying to hammer home to people that this movie will be in movie theaters nationwide. It's now, you know, wherever you live within, you know, 10 or 15 minute drive, there will be a movie theater where you can see it. So, you know, we've put that hurdle behind us. Well, that's good news because I do think it's an important film. And I think

I think it's interesting because the zone of Trump is flooded with so much myth-making about who he is. And my first real encounter with that was way back when I worked for – I was working in the 2016 race for a super PAC. I went to a big donor in New York.

And I worked in New York and I still didn't know that Trump wasn't anything like he was portrayed. I said to the donor, I'm like, look, he's a billionaire. He could self-fund even $100 million, $200 million. It's going to be a real problem. And the guy leans back, he goes, Donald's not a billionaire. Yeah. He's a clown living on credit. And as I started to dig then and with writing two books about it, I felt that you keep peeling back to revelations about how little there is really there underneath it.

Except that bundle of insecurities and his dad's money. You know, right. Right. His, you know, all of his deals. And there's a scene, you know, and I hope you tee up our interview with spoiler alerts, but there's a scene near the end of the film, which is which is based on a real event where Donald is being hounded by creditors. He's trying to build the Taj Mahal casino in Atlantic City. He's totally over leveraged.

And he goes to his father who's dying of Alzheimer's. He's completely out of it. And basically, Donald tries to swindle his own father into giving him control of the family trust so that he can pay back his creditors. And that, to me, really is the essence of the Donald Trump business career. Right. It's a total house of cards.

But he always fails upwards because he had this family money. That $414 million came in very handy for him over the years. It certainly... And I also, one other point I want to make is, you know, this movie is a character study of, you know, what happens when somebody sacrifices their morality for the pursuit of power. And, you know, Donald, when we meet him, you know, he's in the start of the film, he's

still somewhat tethered to reality. He is a human being. And I think under Roy Cohn, he learns that there are no rules. You can do whatever you want to anybody if it gets ahead. And I think that's, you know, for me, that was what was, I think, the most disturbing is to really internalize this feeling that Donald Trump could become president and he's somebody that is just a complete moral vacuum. I mean, there's no humanity left in this person.

And you see it sort of disappearing in the movie. You see it sort of, you know, the, the trade-off is, is, you know, and this, the very traumatic scene in the film of, of his, his rape of Ivana, um, that doesn't, it, it, it, and there, it doesn't seem to have remorse or, or, or to, to affect him. And that, by the way, another great piece of acting in that moment. Um, but it, it, it just strikes me that, that, that that's the inclusion of that scene, uh,

telling that story was one more moment where you really understood that there was nothing left after he bought into this devil's bargain with code. No, I mean, yeah. And, you know, that that scene is obviously very brutal and it was difficult to write and difficult to watch. And I think the actors and the filmmaker handled it, you know, I think with subtlety and respect. But, you know, I think that scene dramatizes that this is what

somebody would do to the person who he's the closest to that he's supposed to love the most. And when she threatens his masculinity,

his response is to just destroy her. Um, and, uh, you know, that scene is based on Ivana's 1990, uh, 1990 divorce deposition. Um, you know, which she later clarified that she, it wasn't criminal issue, but you know, and then she, when Trump was running for president, walked it back further. Um, but I felt that that scene was emotionally true, that her first statement was the most emotionally accurate, um,

most accurate rendering of who Trump was at that time. Right. I think that's the case.

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this moral vacuum, as you called it correctly, I think, and showed people that it wasn't just... It's not just today. This has been what he has been now for almost...

60 years. Yeah. This is the character he's been, or the lack of character he has for almost 60 years. No, I think it's, and that's where I kind of also feel like the film sheds some new light that it's, yes, Roy Cohn was, I argue, you know, the film dramatizes that Roy was Donald's biggest influence, but

The film also explores how Donald was the product of a culture and a system. And in that way, myself as a reporter and a member of the media take some responsibility for that. I think Roy taught Donald how to manipulate the media and use television and use gossip columns to build up this myth. And so the movie is also kind of an indictment of

What happens when politics becomes entertainment? And so I think it's a cautionary tale also just for America. That's a really interesting point because he's always been a creature of page six. And folks, if you don't know, page six is the gossip column in the New York Post every day. But he's always been a creature of page six, even dumping his own stories there, trying to spin himself to them under these assumed names, all this stuff.

All this. And I find it fascinating that in the era of social media, he couldn't have gotten away with it. But he's also very much a successful creature in the era of social media. It is a format that he's shockingly good at. Yeah, but I think that also is a testament to Roy's influence because Roy had a very vivid and colorful personality.

style of speaking. When Roy was being disbarred by the New York Bar Association in the mid-80s for unethical behavior, he called the New York Bar Association a bunch of yo-yos and bozos and clowns and the politics, kind of the ad hominem attacks. And that way of speaking, it's funny. I mean, I think

Roy actually had a very sharp and specific sense of humor. And I think Donald does, too. And that's why I think social media was a good format for him, because Donald, regardless of what you think of him, he is an effective communicator and he speaks in a way that gets people to pay attention. And that was also another lesson of Roy's. Well, I think I think that this is.

a movie that folks should go out and see. I think that it is an insight into Trump that is valuable, especially at this moment. One last question for you. Roger Stone, who I call the dollar store Roy Cohn, sort of rose up to take Roy's place in some attenuated way. He was never quite

Roger's own bullshit has never quite met the myth of Roger, but Cone really was that evil, really was that manipulative. Was Trump just attracted because he needs that sort of devil on his left shoulder figure in his life? Yeah, that's really smart that you mentioned that because there's a character who plays Roger Stone as a cameo in the film. And when I was writing it, the intention of the Roger Stone character was

to show how as Roy got sick and was dying of AIDS, and he was also being hounded by the IRS and the FBI, Donald, you know, he was less useful to Donald. And then Roger Stone kind of enters and takes that, fills that role. And yeah, I think Donald and Donald needs these, you know, these people around him who will basically never, you know, challenge his,

unethical behavior. You know, I think Michael Cohen in a, in a, in a later life ended up playing that role as well. Um, but you know, none of them seem to have measured up, you know, what's the famous line that, that Trump said when he was, um, being investigated, uh, where's my Roy Cohn. Um, right. And there's part of me that sees him and, and, you know, thinks that he still wishes that, you know, Roy's been dead for 40 years, that, um,

you know, the ghost of Roy Cohn could talk to him. I bet he does. I bet he does. Well, Gabriel, I know you are out of time and I want to let you get going. We will put a spoiler alert at the front of this show. But thank you so much for coming on the podcast today. One other thing that people can go to www.theapprenticemovie.com

And no matter where you live, you click on the link to buy tickets and it will show you a local theater. So that was my next question. Spread the word, please. Yeah, absolutely. Absolutely. Well, Gabriel, thank you so much for coming on today. I really appreciate you. We'll talk to you again soon. Okay. The Lincoln Project Podcast is a Lincoln Project production. Executive produced by Whitney Hayes, Finn Howe, and Joseph Werner Chaney. Produced and edited by Whitney Hayes and Jeff Taylor. And good luck.