“The Apprentice,” an incendiary film about Donald Trump’s relationship with his political mentor, opens in theaters today. For screenwriter Gabriel Sherman, it’s a moment that seemed like it might never arrive.
Trump’s lawyers and wealthy supporters threw up various roadblocks to prevent the movie from being released before the election. But thanks to some last-minute legal maneuvering, it’s now showing on over 1,500 screens nationwide.
Sherman got the idea for “The Apprentice” during Trump’s first term in office, when he began looking into the former president’s connection to Roy Cohn. Cohn, the infamous legal counsel for Joseph McCarthy, who also prosecuted Julius and Ethel Rosenberg, has been portrayed as a cinematic villain before — most notably in Mike Nichols’ adaptation of the play “Angels in America,” where Cohn hoards life-saving AIDS medication for himself at the height of the epidemic.
But Cohn’s complex relationship with Donald Trump is unexplored narrative terrain. And the more Sherman read about it, the more fascinated he became.
Sherman, a longtime political reporter at Vanity Fair, was one of many writers who often characterized Trump’s politics as unique and unprecedented back in 2026. Sherman joined The Show to talk about how writing “The Apprentice” made him realize there’s more to the story.
Full conversation
GABRIEL SHERMAN: I think what kind of reoriented my thinking was when I dove into the research and I saw kind of how unoriginal Trump actually is, is, you know, he's, he, he's adopted Roy Cohn's rhetoric and his speaking style, and his three, you know, rules for political survival.
And we see that play out every day on the campaign trail now.
SAM DINGMAN: Yes, but it struck me in watching the movie that there is a key difference between Cohen and Trump. And that for me was really illustrated in the scene where they're in the basement of Roy Cohn's house.
And Cohen is showing Trump all these recordings that he has made of influential people who have been to his house. And he is kind of talking about the reason that he does all these extra legal things in the name of winning these cases
I got the sense in those scenes, that in your framing, in his own mind, at least Roy Cohn was a real patriot.
SHERMAN: I mean, a deeply cynical one. But yes, he did justify a lot of his malfeasance through this, this idea that he has to save the country from communism. You know, that that scene was partly inspired by Roy Cohn's memoir. Shortly before he died, he did these series of interviews with the journalist Sidney Zion. And the Rosenberg case was a big part of it.
And, you know, I was reading the book, I just found it chilling to hear Roy bragging about, you know, breaking the law and going, going out and calling Judge Kaufman during the trial and having these off, you know, off the record side conversations, trying to influence the judge. You know, obviously, regardless of what you think about the Rosenbergs and whether they committed treason or not, you know, the idea that these people were executed in a way that, you know, violated the due process of our legal system.
It showed to me like the depths of depravity that Roy was willing to go to, to, you know, fit this ideology of quote “saving America.”
What's interesting to me is that after Roy reveals this to Donald, he doesn't shy away. He, he's, he's fully in, he's on board with this.
DINGMAN: Another thing it seems like you're after and, and tell me if this is the case is there's a very interesting contrast between Trump's relationship with his father, his biological father, Fred Trump and his relationship with Roy Cohn.
SHERMAN: That was one of the bigger strands that I wanted to pull on when I was writing this film, is Donald was seeking validation from somebody who, you know, he didn't get it from his own father.
You know, Fred Trump did not respect Donald's desire to build in Manhattan. He thought Manhattan was, you know, going down the tubes that the city was bankrupt, that there was no, there was no way that a luxury hotel would, would pay off. Fred's provincial worldview kind of drove Donald closer towards Roy because Roy was this cosmopolitan high flying member of society.
You know, but the other thing that I thought was so fascinating about this relationship between Trump and, and Cohn was not only the father-son dimension, but the homoerotic tension.
Yes, he saw him as somebody that he could be a protégé and, and propelled to the elite of New York society. But, I also thought he was in love with Trump. The conflict in the film really centers around people who enter Trump's life, who tried to take his attention away from Roy.
And so, you know, you have Ivana taking Donald away, you have Roger Stone coming in starting to take Donald away. You have this father, son/homoerotic love story. I think it shifts, it goes back and forth and that ambiguity is really interesting to me.
DINGMAN: There is this very interesting moment where I think we, we don't know yet that Cohn is sick with, what was later revealed to be AIDS. But, he is clearly starting to feel the effects of it and they're literally driving through an AIDS protest.
SHERMAN: Trump has this almost, you know, physical aversion to people who are sick or weak. As Roy was deteriorating in his, his health was declining, Trump, you know, pulled away from him.
You know, he just couldn't be around somebody who was not making him feel stronger.
DINGMAN: Well, I found that all of a sudden the character that I empathized most with in the back half of the movie was Roy Cohn and that felt strange. And one of the most compelling moments where that happens is this scene where Trump throws Cohen a birthday party at Mar-a-Lago and he brings out for cone who at this point is very sick with AIDS, he brings out this birthday cake with sparklers coming out of it and you see Cohn, look down at the cake and it, it looks like the American flag is on fire. And Cohn just starts weeping.
SHERMAN: Well, that scene, first of all the scene happened, Donald did throw Roy a kind of a farewell dinner shortly before he died of AIDs at Mar-a-Lago, I felt like if Roy Cohn who's widely, you know, regarded as, as, as, as, as an evil figure in the American imagination, if he could feel betrayed by Donald Trump, what does that say about Trump himself, right?
If Donald Trump could hurt somebody who is considered to be a monster? Well, if that monster is scared of an even bigger monster, I think that kind of illustrates how this in some ways this is a Frankenstein's monster kind of story, right? You know, Roy taught Donald these lessons and then it kind of got out of his control.
