‘The Apprentice’: Donald Trump, Roy Cohn, and the Pursuit of Power
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Hey, it's Latif from Radiolab. Our goal with each episode is to make you think, how did I live this long and not know that? Radiolab, adventures on the edge of what we think we know. Listen wherever you get podcasts. This is On The Media's Midweek Podcast. I'm Brooke Gladstone.

The new film, The Apprentice, takes us back to New York in the 1970s, to when Donald Trump, played by Sebastian Stan, was just starting to make a name for himself, and when he was introduced to Roy Cohn, the ruthless attorney and political fixer.

What's your name, handsome? I'm Donald Trump. Donald Trump, nice to meet you. Roy Cohn. The Roy Cohn from all the papers and everything? That's right, the Roy Cohn from all the papers, that's right. Yeah, you're brutal. I'm brutal, that's right. He's the guy who put the Rosenbergs in the chair! Guilty as charged. But whatever I do, I do it for America.

Cohn, played by Jeremy Strong, was infamous for investigating suspected communists along with Senator Joseph McCarthy and for securing the conviction and execution of both Julius and Ethel Rosenberg in the 1950s.

This fictionalized depiction of real events shows Cohn molding Trump into his protege, imparting his political lessons on how to wield political power, to manipulate the media, and to bend the truth.

Now, The Apprentice faced some big hurdles procuring financing and distributors and legal threats from the Trump team, too. But it finally opened in theaters in the United States on October 11th. And on Monday, Trump wrote on Truth Social, "...it's a cheap, defamatory, and politically disgusting hatchet job put out right before the 2024 presidential election to try and hurt the greatest political movement in the history of our country."

I sat down with screenwriter and executive producer of the film, Gabriel Sherman, on Friday. Welcome back to the show, Gabe. Thanks for having me, Brooke. What were you going for by focusing on his formative years? An explanation? A truth about a man who lives explicitly by the principle that there is no truth?

Well, Brooke, you know, I'm a political journalist in addition to a screenwriter, and I covered Donald Trump's 2016 presidential campaign for New York Magazine, where I was working at the time. And I was struck by things people like Roger Stone and others who had known Trump since the 1980s had told me that when Trump was giving his rally speeches, he sounded a lot like Roy Cohn or he was using phrases that Roy Cohn used to use.

And it came to me one day in a flash in the spring of 2017, shortly into the Trump presidency. I said, you know what? There's a movie in that, this relationship between the second son of a middle-class housing developer from Queens who falls under the sway of a right-wing, closeted, corrupt lawyer and learns the lessons that he would later apply.

apply to American politics. I thought focusing on a movie that looked at that one relationship could explain a lot more. And the other thing I thought, Brooke, is that yes, we're inundated with Trump content every day on the internet, on TV, social media, but information has a way of numbing us. We're so overloaded with information that I thought writing a story that has a dramatic impact could make the audience feel

Something on an emotional level that the news is sometimes difficult to convey, you know, drama and art are really good about conveying emotion. And so that was my attempt is to sort of strip away the politics and try to write about Donald Trump as a human being.

What emotions were you trying to evoke? You know, Donald Trump did not come out of the womb formed as he is today. You know, there's a really fascinating interview that he did in 1980 with Rona Barrett. I believe it's his first nationally televised TV interview. And I recommend the listeners to, you know, you can watch it on YouTube. Is there anything you can't have materialistically or emotionally? Is there something that your money cannot buy?

Well, it's a very nice question, Ron. I'm not sure that there's an answer to it. I mean, I'm quite happy with everything. I'm quite happy with the way everything's worked out for me at this point. Now, if this point hasn't been very far in 10 years, if we sit down at the same situation, maybe I'll tell you, Ron, you know, I've made mistakes here and mistakes there, which today I don't think are mistakes.

But at this moment, I would say, by the way, money is not the ingredient. Money has nothing to do with the ingredient. It just whether I was a, you know, an artist and just pushing my work and enjoying my work, whatever it is, I think you just have to be happy in what you do. You can see in this interview how tentative and soft spoken he is. He's articulate. He's charming. He's polite. It's just it's a world of difference from the Trump we know today.

And I think seeing the transformation of a character over two hours in a film, you know, makes the audience see that, you know, monsters are created. They're not born. And the other thing I wanted to make audiences feel is that we are all in a certain way complicit in the election of Donald Trump because, you know, Donald Trump's rise in New York real estate in the 1970s and 80s.

and 80s, you know, was aided and abetted by New York, quote, liberal society, the New York media, the tabloids. And so he's not an alien from outer space. He's a product of a system and of a time and a place. I'm all for pointing out our complicity. Love to do it. But in the case of Donald Trump, the complicit were very much among not the readers of the New York Post, but the powerful class.

And his ability to use Roy Cohn to threaten and blackmail and otherwise break the rules. I think that he could never have risen if it hadn't been for corruption at the heart of...

government and the real estate industry. Without question, that's a great point that you make. And the movie shows in very intimate detail how Trump's relationship with Roy Cohn really opened the doors of power and the halls of influence to him. Roy Cohn's client list in this time was the who's who of New York power. People from Rupert Murdoch to Yankees owner George Steinbrenner

publisher, Cy Newhouse. To Andy Warhol. Andy Warhol, and also the heads of the New York mafia families. You know, Roy Cohn was really the intersection between the legitimate world and the underworld. And Donald Trump, as we know from his entire career, he operates in that gray zone between, you know, criminality and legitimacy. And that was a lesson that he learned from Roy Cohn. Mm-hmm.

And when the film begins, as you mentioned, Sebastian Stan plays a soft-spoken, maybe bumbling version of Trump, one that we're not used to seeing. And then he ultimately adopts, minus maybe the loyalty, Cohn's worldview. So let's hear Jeremy Strong cite Cohn's rules for success. Roy Cohn's three rules of winning.

The first rule is the simplest. Attack, attack, attack. Rule two, admit nothing, deny everything. Rule three, this is the most important rule of all. Okay, no matter what happens, no matter what they say about you, no matter how beaten you are, you claim victory and never admit defeat. Never admit defeat. You want to win, that's how you win.

Are these really the lessons that formed the Trump that we know? They are. You can boil this down and look at every single Trump strategy and tactic, and he's applying one of these three rules. What I find so revealing about this movie is that when you see that he grifted Roy Cohn's personality, we bring him down to earth because we realize that there's really little that's original about this person, that he's an amalgamation of another man's personality.

And in the end, we do see Trump spouting Cohn's views as his own to Tony Schwartz, who wrote Trump's bestselling The Art of the Deal. What else did he learn from Cohn's other rules? Roy Cohn had the gossip columns in New York City on speed dial. And there's a line in the film when Roy, played brilliantly by Jeremy Strong, tells Donald, like, you got to keep your name in the papers. And it's sort of a throwaway line. Rupert is going to be key for you.

You want to get quoted in the post and all the papers are locked. These lessons that the only truth that matters is what you can present to the world, all

also became foundational to Donald Trump's strategy. And I think also Roy told Donald that the only thing that mattered was winning. There was no morality. There were no rules. The only thing that mattered was did you get what you wanted and do you have more power? And that is essential to understanding Donald Trump. Another one of Cohen's rules is counter-sue if you're getting sued or threaten the lawsuit if you're pissed off.

Just use the law as a cudgel. Exactly. And this really, I think, established also the idea that there are only narratives. There's no truth. And, you know, we remember Kellyanne Conway's famous remarks that there are alternative facts. Don't be so overly dramatic about it, Chuck. You're saying it's a falsehood and they're giving Sean Spicer, our press secretary, gave

alternative facts to that. But the point remains that there's- And that was really part of Roy Cohn's lesson is that if you file a countersuit, now it's not a question of who's right and who's wrong. It's your claims versus my claims, and we can duke it out. And this legal strategy also became part of Donald Trump's political strategy later on. There's a famous quote about Roy Cohn, and it goes something like this, that he was a lawyer who had contempt for the law.

And I feel like Donald Trump is a politician who has contempt for the institutions of American politics. You know, these are not institutions that are supposed to be upheld. These are institutions that exist to maximize his personal power and his financial gain. And these are, again, just values, I would say, anti-values that he learned from Roy.

And you talked about how you offer a counter story and it works in court and it works in politics. And it strikes me it works perhaps best of all in the media, at least in the legitimate media that wants to bend over backwards to show that they're offering two sides, even if one is completely bankrupt of truth.

Roy Cohn taught Donald Trump to exploit that and take advantage of reporters' willingness to make sure that the other side, even if it's a bunch of lies, is heard. And I think the media has gotten better at that, of not platforming in both sidings.

Not a whole lot better, Gabe. When I think about, for instance, the big Peter Baker piece in The Times about Trump's... Declining mental state. Precisely. I mean, he could have done that story any time. The Times could have run it any time. Correct. On the same page where they were running the same sorts of stories, speculating about Joe Biden. Yes, that is true. Trump is clearly displaying the signs of mental decay.

And yet they're just covering it like it's just a regular news story. So yeah, I think he raised a good point that even in 2024, after we've had almost a decade to learn how to cover Trump, that he's still so outside the bounds of how people behave. And this is also a Roy Cohn lesson. You know, if you're willing to go to a place that anyone with a conscience would never do, it's so difficult for the media and institutions to even sort of process how to handle that.

So this is a fictional dramatization of real life events. Tell me about your research and the fact checking that went into the film. You know, the film, as we say at the top in a disclaimer, it is not a documentary. It is not journalism. So I don't want it to be judged as such. I want people to experience this as a film, as a piece of cinema. That said, all of the major turning points in the film

are rooted in actual events. And I've had friends come up to me and say, "God, this stuff is all so crazy. Like, how did you make it up?" Here's an example. Like, in the opening scene when Trump meets Roy, he sees Roy Cohn put Sweet 'N Low into his champagne, which sounds utterly disgusting.

And that's a real character detail that I found in an early profile of Roy. It's so weird and idiosyncratic that I as a screenwriter don't have the imagination to even make up a detail like that. So the stranger than fiction details in the film, the vast majority just come from real life.

Let's talk about the rape of Ivana Trump. She made that allegation, and this is a really brutal scene, that Trump violently assaulted her and she said it under oath during a divorce deposition. But then she seemed to take it back.

So in 1993, Harry Hurt was publishing a biography of Trump called The Lost Tycoon. He's a very good journalist, and he obtained Ivana Trump's divorce deposition, the documents that quote her statements under oath. And under pressure from Trump's lawyers,

His publisher included a statement from Ivana that clarified it was not a retraction. She clarified that she didn't mean rape in the quote criminal sense that she felt violated as a woman. So to me, that's what we call a non-denial denial.

And then subsequently in 2015, 25 years later, when he was running for president, she says, you know, Donald and I are the best of friends and basically takes it all back. And to me as a screenwriter, I look at the totality of these statements and what feels the most emotionally true to me, what feels to me the statement that she made under oath

closest to the event in real time with the highest penalty of lying was that first statement. The subsequent statements, there was really no penalty for if she was changing her story. So this is a fictional film. It's based on real people. And the character of Donald Trump in the movie, when this brutal scene happens, to me, it is perfectly within the character of the film. And so I felt it was...

essential to include it. And it was essential to include it also because the real Donald Trump has been credibly accused of sexual assault by at least a dozen women. I think a dozen women or more. He was found liable by a New York jury of assaulting the writer E. Jean Carroll. So this is clearly a part of his character. He boasted on the famous Access Hollywood tape that he gropes women. And so I thought that a film that explores his

His origin story had to reckon with his violent treatment of women. And so that's why as hard as it was to write, and of course, as hard as it was for these actors to perform the scene, I don't think the movie would be authentic if it didn't include it. And speaking of that scene, among others, the Trump campaign calls the film a hit job.

But other critics have said you didn't go hard enough on him. And still others say, is this an October surprise, given the timing of its release?

How do you respond to all of these controversies and questions? First off, I welcome it. I love people debating this film. It means it's resonating in a certain way. But on the politics side, this is not a political film. And I know your listeners might roll their eyes when they hear me say that. How can you write a movie about Donald Trump and it not be political? But it's true. When I sat down seven years ago to write Politico,

the screenplay, it was an honest attempt to understand him as a human being, to tell his story as a gritty New York story. My aspiration was that it would be in the pantheon of New York films like Taxi Driver, The Godfather, Dog Day Afternoon, or Midnight Cowboy. These were my cinematic references. I get that, but right now, by dint of its timing, it's unbelievably political.

When we started financing this movie, it looked like Donald Trump's political career was over after January 6th.

and his indictments. There was a moment when, you know, it looked like Ron DeSantis was going to be the future of the Republican Party and Donald Trump was just going to go away. And so, you know, we're getting this movie off the ground. And it just so happens that once the movie finishes shooting, Donald Trump is in a competitive race for president. And I'm embracing it. I think, you know, the fact that it is coming out during an election helps create awareness for the film, but it was not a master grand plan of ours.

The depiction of Cohn by Jeremy Strong, as you mentioned, is brilliant. The depiction of Trump is also remarkable, maybe even more so because his transition

is so subtle. People might not recognize the Trump we know now from those early scenes, but you certainly would later. And I just wonder whether Sebastian Stan, we don't have him here to talk about his process, you know, what did you notice about that? Sebastian, I think, had the harder challenge because Donald Trump is so omnipresent in our culture. He had to find

a character that felt real to a movie audience that did not feel like an impression. He read the movie in 2019 and wanted to do the role and we didn't have money to film the movie, but we stayed in touch. And I would get these voice memos from him as he was driving around Los Angeles and he would be practicing the voice and rehearsing.

And it was always a treat because I could see him over the months and years it took to get this movie made. He was finding the character and finding the voice. He has an incredible voice coach. And they together found this character that feels...

entirely real when people see it. A point of Trump's character in this film is that he wasn't born this way. And so I think Sebastian wanted to introduce the character of Donald Trump in a place where audiences are like, wait a minute, this isn't who I expect. And they can get invested in the character. And then by the last frame of the movie, he resembles the Donald Trump that we all know today. And it's that arc that really drives the movie.

So you mentioned that the film had an uphill battle to get the funding. Also, every major Hollywood studio and streamer refused to buy the movie because they didn't want to get sued.

It's been touch and go about whether this film would ever be released. There was a moment after its world premiere at the Cannes Film Festival in May where I doubted the movie would ever be released anywhere because the contract stipulated that it had to come out in America before it was allowed to be released in other countries. So if we didn't find an American distributor, for all intents and purposes, the movie would be shelved.

And to me, it was a chilling example of how the media industry has preemptively censored and chilled itself to not get on the wrong side of Donald Trump. You know, these big studios and streamers did not want to face punishment from Trump. Should he become president, he could use the regulatory power of government to go after their businesses. He already demonstrated that he did that. Years ago, he tried to block, the Justice Department tried to block

the AT&T merger with Time Warner, the parent company of CNN, because as we all know, Trump calls CNN the enemy of the people. So, you know, these companies saw the writing on the wall. And while I find it disappointing, I understand their business logic. And so we were the casualty of that. We found a small independent distributor company.

called Briarcliff Entertainment, who had the guts to take it on. Didn't Briarcliff also take on one of Michael Moore's films? Yes. So Tom Ortenberg, who started Briarcliff as a veteran Hollywood executive, he has a track record for distributing controversial films in his previous jobs as

He distributed Fahrenheit 9-11, the Michael Moore film, as you mentioned. He distributed Oliver Stone's movie W. And he also distributed the Academy Award winning film Spotlight, which investigated the Catholic Church.

So Tom's not a wilting flower. Tom doesn't back down. While he has guts, he doesn't have a lot of money. So when a studio launches a film theatrically, they spend millions and millions of dollars on advertising. And we had to do a Kickstarter campaign

to turn to our own audience to help buy advertisements to get the word out about this movie. So nothing about this film has been traditional. You know, I'm just grateful that it's now out in the world. But, you know, we're still trying to get the word out because we are, you know, this small pirate ship in the sea of Hollywood. What do you think is the quintessential moment in the film?

For me in the writing, there's a moment when there's kind of a no turning back moment. When Roy takes Donald into his basement lair where he secretly tape records his conversations with clients and adversaries to get compromise on them. And he reveals this taping room to Trump and basically says, I'm

I'm willing to do whatever it takes and get any leverage I need to win. And Trump faces a choice at this moment because he's won the lawsuit that he hired Roy Cohn to represent him. He could kind of go a separate way. And when I wrote the movie, that was the moment when Donald fully commits himself to his new master. Well, that's illegal. Oh, it's illegal? Donald, wake up.

You know, when I tried the Rosenbergs,

I wanted so badly to see those pinko kikes fry for what they did. Now, Judge Kaufman had no trouble sending Julius to the chair, but Ethel was a mother with young kids. They wanted her to live, as if that's some sort of special immunity for betraying your country. So during the trial, I'd slip out at lunch to a phone booth and call Kaufman.

You know, technically ex parte conversations, they're not allowed. But when democracy is at stake, you're damn right I'm willing to violate the few technicalities. I don't care if she's a mother with young kids. She betrayed our country and she has to die.

Director Ali Abbasi said that one of the things that really resonated with him was that he wanted the film to expose the system as much as it reveals the characters. That's correct, Brooke. I mean, the movie has very little political discussion itself. Like the characters, they talk about democracy and anti-communism, but...

You know, the ideology of Donald Trump is very thinly represented in the movie. It's about his character in terms of what is he willing to do to advance his own personal and financial agenda. So my producer and I, after we had a version of the script that we felt was strong enough to start sharing with people, this was way back in 2018, our instinct was to always try to hire a non-American filmmaker to take on the subject because we thought

Having somebody outside of our system look at this character with a fresh set of eyes might yield something really original. And Ali's main note when he first read the movie is he told me that he wanted this film to expose American capitalism and corruption and how power is wielded.

As much as you wanted to illuminate Donald Trump's character, this movie, I think, exposes that the system tolerates unethical behavior. And the only thing that matters is whether you can get away with it. There are some grotesque scenes, one showing Trump's liposuction and scalp reduction procedures. Was the yuck factor a crucial part of this project?

It was. And this was also Ali's influence. He really helped me focus and draw out the Frankenstein aspect of this story, you know, the actual physical manifestation of the monster. And so, yes, the body horror at the end of the film was very intentional.

It's, you know, it's a visual metaphor. It's an emotional tool. And, you know, I've had friends kind of compare it to when, you know, Anakin Skywalker puts on the black mask and becomes Darth Vader. That was the intention with why we felt it was so important to include those scenes. Gabriel Sherman is the screenwriter and executive producer of the film The Apprentice. Gabe, thank you so much. Thanks, Brooke. Thank you.

Thanks for tuning in to On the Media's Midweek Podcast. Be sure to check out The Big Show. This week, it's all about new developments in the old story of money and politics. And it posts on Friday around dinnertime. Bye.