Episode 118: Gabe Sherman on writing “The Apprentice”

By: Greg Iwinski

Host Greg Iwinski sits down with Gabe Sherman to talk about Gabe’s path from New York real estate journalist, to writing a book about Roger Ailes, to writing a movie about one of the most famous people on earth: Donald Trump.

Gabe Sherman is a journalist, author and screenwriter known for writing The Loudest Voice in the Room, the 2014 bestselling biography of Fox News president Roger Ailes. As a journalist his work has appeared in publications like The New York Times, The New Republic, The New York Observer and GQ. He previously served as national affairs editor at New York magazine and is currently a special correspondent for Vanity Fair and a regular contributor to NBC News and MSNBC.

Most recently, Gabe wrote the screenplay for The Apprentice, the 2024 feature that follows Donald Trump’s career as a real estate businessman in New York in the 1970s and 1980s, as well as his relationship with lawyer Roy Cohn. The Apprentice was released in the US on October 11, 2024 and is now playing in theaters.

This episode of OnWriting is hosted by Greg Iwinski. Greg is an Emmy-winning comedy writer and no-award-winning performer whose writing includes LAST WEEK TONIGHT and THE LATE SHOW WITH STEPHEN COLBERT. He recently finished writing the first season of GAME THEORY WITH BOMANI JONES on HBO, and can be found on Twitter @garyjackson.

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OnWriting is an official podcast of the Writers Guild of America East. The series was created and is produced by Jason Gordon. Associate Producers are Molly Beer and Tiana Timmerberg. OnWriting’s Designer is Molly Beer. Mix, tech production, and original music by Taylor Bradshaw.

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Thanks for listening. Write on.

Transcript

Greg Iwinski: You are listening to OnWriting a podcast from the Writers Guild of America East. In each episode, you’ll hear from the union members who create the film, TV series, podcasts, and news stories that define our culture. We’ll discuss everything from inspirations and creative process to how to build a successful career in media and entertainment. I’m your host, Greg Iwinski, and today I’m speaking with Gabe Sherman, writer of The Apprentice, a feature film that looks at Donald Trump in the seventies and eighties as he’s being mentored by Roy Cohn.

In this episode, we’ll talk with Gabe about his start as a New York real estate journalist writing a book about Roger Ailes, and then writing a movie about one of the most famous people on earth, Donald Trump. And fair warning, we have a ton of spoilers for The Apprentice in this, so make sure to go see it first before you listen to the episode. I’ll wait. You just have to hit pause. Gabe, thank you so much for coming.

Gabe Sherman: Good to be here.

Greg Iwinski: Excited to talk to you about your career and this film and everything in between. Now you write in print, you’ve written books and written for Vanity Fair and done a lot of that. Talk to me about young Gabe wanting to write. Did you want to write what kind of stuff? Now you’re doing two mediums. Is that what you always wanted to do? What is that journey like getting to writing?

Gabe Sherman: Well, going way back to my childhood, I first and foremost loved movies. My older brother’s seven years older, so I spent a lot of time alone because the age difference and parents were busy working and in the eighties just fell in love, the era of VHS, just watching old movies over and over again. I think I watched Fletch maybe like 25 times and The Right Stuff.

Greg Iwinski: So that’s a hint into where you’re going. You’re watching Fletch as a kid.

Gabe Sherman: Yeah, I guess maybe that’s why I ultimately became a journalist at some point or The Right Stuff or some of these seminal films from the eighties were big parts of my childhood, and I think I didn’t have a specific idea of what kind of writing I wanted to do. I wasn’t one of these newspaper kids who worked on the high school paper and then the college paper. I studied politics in college and just after graduating in 2001, got myself an internship at a local paper here in New York and just felt like I had discovered I had a knack for reporting, for synthesizing information, for getting people to tell me things that they probably shouldn’t. And I just fell in love with it and that was sort of set me on my way.

Greg Iwinski: And so you saying you graduated in 2001, so you jump into politics reporting and that world of writing as the definitional event of a millennial’s life and the news happens, changes, what war is changes. So kind of going from then till now, talking about what the Trump administration you’ve been able to professionally see, start to finish an entire, maybe not finish, but seen a whole era of politics.

Gabe Sherman: Yeah, funnily enough, my first job in journalism wasn’t covering politics, it was actually covering real estate. I wrote a column called Manhattan Transfers for the New York Observer, which was basically chronicling the most expensive apartment sales every week, trying to scoop the other papers that covered real estate and then occasionally also writing longer pieces. I ended up interviewing Trump many times when I was in my early twenties. This was before The Apprentice when he was sort of floating around sort of post-bankruptcy, but he hadn’t reinvented himself as a reality TV star, and he apparently had a lot of time on his hands because I could call his office and his assistant, Rhona Graff would answer, and then 10 minutes later she would call back and say, “I have Mr. Trump for you.” And I’m like a nobody cub reporter at the time.

But yeah, so just in that context to kind of bookend the last 20 years of, I started writing about Trump as a real estate blowhard here in New York, and then 20 years later, he’s 15 years later, he’s the President of the United States. It’s kind of a, to kind of be in the middle of that surreal arc, I think gave me a connection to this story and an ability to write this dramatically that maybe other writers didn’t have a connection to.

Greg Iwinski: Yeah, and before you wrote this, you wrote about another, I’m trying to be politic-

Gabe Sherman: Right-wing media figure.

Greg Iwinski: Yeah, I’m trying to be politic-

Gabe Sherman: No, you don’t need to be [inaudible 00:04:14]-

Greg Iwinski: So I don’t get trouble. Guy who I’m not a fan of, Roger Ailes. And you wrote about that and that was a project with Tom McCarthy and working on that. So moving from that to this, writing this by yourself, what were some lessons you learned from writing that also as a series, having a little more time to stretch it out? What were some lessons from that experience?

Gabe Sherman: Yeah, that’s a great question. That was my first introduction to show business. 2014, I published a biography of Fox News founder Roger Ailes. I always thought of when I was writing the book, Ailes was such a larger than life cinematic character. He was like a modern day Citizen Kane. And I always felt like that there was definitely dramatic potential in this material, whether it was fictionalized or adapted as based on true events. Ultimately, Showtime did option the book and set up the show, and Tom McCarthy came on as our executive producer and my rabbi and screenwriting. And yeah, I mean, I think, gosh, so many lessons. I think the first part, just sort of putting television, comparing television to feature writing, doing a series of television requires so much story engine you’re trying to set up obviously your main character, which was Ailes. But also we were trying to build out the culture of Fox News.

When I created the series, I always imagined writing the show as if Ailes was a cult leader. So not writing it as a television network, is sort of writing it as a mini Scientology where he’s the L. Ron Hubbard in the middle, and then everybody in this sort of secret society operates by his own nefarious rules. So there’s a lot of characters, secondary characters to set up. And then when I moved into feature writing, when I came up with this idea to write The Apprentice based on the relationship between Donald Trump and his mentor, Roy Cohn, a feature is really just sort of trying to answer one question. You’re really exploring just one core relationship. And I found it really satisfying because in 120 pages you can tell a complete story. Whereas I find sometimes when I’m writing for television, there’s so much pressure at the end of an episode is to come up with some twist something to spin it into the next episode. It was a different, it just sort of required a different metabolism.

Greg Iwinski: I actually want to jump a little bit off-topic and dive deeper into this idea because what we see now, and I think audiences see across television is, especially with prestige networks and things, is you see these shows that are six episodes, maybe eight episodes, and you hear again and again, “It could have been a movie.” “It’s a long movie.” Or then you see a movie and then people want the director’s super extended cut. And so now that you’ve done both, how would you delineate if you had a story you loved between this should be six to eight, hour long episodes or it should be a film?

Gabe Sherman: It’s a great question. I think, I mean, there’s no science to it. It’s sort of instinctual or sort of my gut feeling. I think the material, I sometimes feel like if you know producers on the phone are like, “Okay, we want to do this for six, eight episodes.” And I’m like, “Maybe it’s four.” If you’re stretching it, I feel like then listen to that voice. Because once you get into the writing and the breaking of the story, the audience is going to know if there’s not enough there, if it feels thin. And I do, I totally agree with you. I see there’s been several shows over the last several years as the streaming bubble created so many new shows. You’re like, “This was okay, but this could have been a movie.” And I think audiences are somewhat recognizing that. And you look at the success of Oppenheimer. You could have done, Chris Nolan could have done Oppenheimer as a 10 episode limited series. But there’s something really impactful about just sitting down and consuming a story in one sitting.

So yeah, I mean, I think the pendulum is always swinging back and forth. I mean, now we’re in this, I just was reading coverage of the new film, The Brutalist that premiered at Venice, and it’s three and a half hours and it has an intermission. So it’s like we’re in this nebulous world, where is that a movie or is that a theatrical limited series of two episodes? So I think hopefully the stories will find the right format for the story because the commercial pressure producers always want to, you can make more money selling eight episodes, but creatively, sometimes that’s not the best strategy.

Greg Iwinski: I know definitely there are more cinematic stories that are stretched out over episodes, but coming from comedy, I always think of it as if it’s about the story, it’s a movie. If it’s about the characters, it’s a series. And that works with every sitcom where it’s, we just take these five people, anything happens to them in a half hour, it’s over and it hasn’t progressed. So talking about this movie, I think before we talk, because I want to talk a lot about the writing and the conceptual part of it. But the kind of headlining part at the beginning is you make a movie about Trump that wasn’t made by him, so he doesn’t like it. And in a situation now where coming out of Cannes, you have a hard time getting distribution in the United States.

Gabe Sherman: Yeah.

Greg Iwinski: And so having known him and also you clearly can pierce through Trump’s moves based on what you put down in the movie, what is that experience like of having him or his bubble come at you trying to stop the movie from coming out?

Gabe Sherman: Well, on a personal level, it was, I’ve been through this dance before. Roger Ailes ran a smear campaign when I was writing my biography of him, tried to pressure my publisher into not publishing it. And so this is a playbook that the right-wing does to try to police stories that they don’t like. On a creative, as a writer sort of approaching Trump as a character, I found it really satisfying in a way, in a perverse way, because he was just validating the thesis of the movie. I mean, he was by threatening this preemptive lawsuit after our Cannes premiere in May, he was following Roy Cohn’s first rule that he spoiler alert reveals in the movie, which is the first rule of winning is always attack, attack, attack. And what was Trump doing? He was just doing that. So I felt it was like he was actually just, life was imitating art in a way.

But then on a professional level, I found that experience, and we can get into this maybe later, because I’d love to talk about the creative process of the movie rather than the selling of it. But just briefly, I found Hollywood’s fear of whatever legal action Trump would take to be really disappointing. Trump threatens to sue the mailman. I mean, a threatened lawsuit by Donald Trump, it’s like breathing for him. And so again, I’m not a studio executive, but that was such free publicity. Every movie now is trying to cut through this morass of information that we’re all taking in. And here was a movie that was generating headlines, and yet every major studio and streamer wouldn’t buy the movie. And I found it to be just sort of a really disappointing snapshot of the current state of Hollywood because we’ve had so much consolidation, studios merging, big tech companies coming in.

Big tech companies want to create shows for their global platform that don’t offend anybody. And it just made me fear for artistic in this environment where if you look at the films in the seventies, All the Presidents Men, Chinatown, all the kind of great politically hard hitting movies of the seventies. I wondered if those would ever get made in this environment. So that was sort of my existential feeling about the state of the business. But thankfully Hollywood happy ending. We did find a distributor, Tom Ortenberg, who runs Briarcliff Entertainment, and the movie will be out on October 11th.

Greg Iwinski: Which is great. And I think you’re right in that the lack of risk taking is something that is really crippling a lot of the industry, not even just politically, just in any idea that’s a risk. Everyone would rather not take a risk and be safe than maybe take a risk and be successful. Nobody wants to be the genius who took the risk.

Gabe Sherman: I mean, if you look at Barbie, which was green-lit years ago before I think probably the crazy Hollywood contraction, that was a movie that was making fun of the product it’s ostensibly trying to sell. And it was a massive success, made a billion dollars. And I think if Greta Gerwig walked into Warner Brothers today and in this kind of cautious environment and pitched this kind of totally out there pastel pink idea of Barbie, I don’t know if they would’ve taken a risk on it. And that totally worked. And I think I wish those examples, or even Oppenheimer, we just talked about, who wants to a three-hour movie about a scientist with almost no special effects and no chase scenes, and again, billion dollars.

So I always am reminded when these movies are massive hits like the Bill Goldman in Hollywood, “Nobody knows anything.” And that’s where I hope the lesson coming out of this, if post-strike, post-COVID is that it’s better to take a risk and fail than to just make something cautious that nobody remembers. What’s the point? There’s easier ways to make money. None of us do this because we do it for the money. We do it for whatever reason we want to express ourselves. And if you’re failing at that, I feel like then it’s missing the point of what we’re doing.

Greg Iwinski: And speaking of what we’re doing in the creative process of this, something I thought was so interesting about this movie is you like me and many, I come from late night, was it Last Week Tonight and Colbert. And so I have watched thousands of hours of Trump. I think it’s one of my, it’s a story I always tell, which is that I called him saying he won the election in 2020, like 15 seconds before he did it in our work Slack. I was like, “He’s going to say he didn’t lose”. And then he did. And I was like, “I know you.” And I talked to people about the snake poem all the time, you whatever.

So the people whose brains have been soaked in this guy, but I think everyone from how we talk about him at Last Week Tonight to how James Austin Johnson does him on SNL to even more serious portrayals like this. All these writers and creators have in your head, you have an idea of who the guy is and how he works. And so I’d be interested in, you’re sitting down to write this movie and to start in your head, and we don’t have to get into all the politics or whatever, but just to you as a writer, who is this guy? What are the moves or the impetus, what is the machinery in here that’s interesting that you wanted to show?

Gabe Sherman: I mean, the character that I wrote is I wanted to start the film in a very different place than we end up. And just actually stepping back from that, I knew the only way to write a Trump movie for me was to write a movie that had nothing to do with the present day. I thought, anytime you’re approaching current Trump, you’re going to dangerously tread into SNL territory. It’s just he’s so omnipresent. He’s on every screen, he’s on our phones. You cannot escape him. And no matter how brilliant an actor or talented or writer or director, it would be very hard to do a present day version of Trump that doesn’t feel like comedy because he’s everywhere. So I was like, okay, that’s not possible. But I was like, where did he come from? This sort of origin story question I started to get really interesting because he’s a much younger person.

If we end the story when he’s in his late thirties, that’s physically and emotionally still a very different person than a seventy-five-year-old man now. So I thought that could prevent the uncanny valley of it descending into impressionism or sketch comedy. So that was one thing I thought, okay, let’s do Trump early years. True Genesis or the origin of this film was that I covered Trump’s 2016 presidential campaign for New York Magazine. I interviewed him, I traveled to Mar-a-Lago, went on the road. And when I was covering the campaign, people who worked for him since the eighties, like Roger Stone said that Trump was just using the rhetorical techniques that Roy Cohn had taught him. Attack, attack, attack, deny everything, never admit and always claim victory, those three rules. And as you said, he did that after the 2020 election. “No, I didn’t lose.” And so I was like, okay, well that relationship, this mentor-protege story is sort of the kernel of a movie.

And then and so I did more research, it has this sort of tragic Shakespearean arc where, as Donald’s fame rises by employing Roy’s lessons, Roy’s power declines because he’s being investigated by the IRS for not paying $7 million in taxes. And his boyfriend gets AIDS and dies of AIDS. And then Roy famously gets AIDS and denies it says it’s liver cancer, but his health fails. And as this, as Roy’s star, it’s sort of a star is born arc as Donald’s star is going up, Roy’s going down and Roy’s real moment of need, Donald cuts him loose. Donald’s famously a germaphobe, didn’t want to be around Roy with AIDS and hired new lawyers. And Roy, there was this famous quote, I think it was in Wayne Barrett’s book about Trump, but Roy was quoted as saying, “I can’t believe he’s doing this to me. Donald pisses ice water.”

And I was thinking to myself, I was like, if Roy Cohn’s widely considered to be one of the most evil people, the 20th century Ken Auletta, the New Yorker writer who wrote an amazing profile of Roy Cohn for Esquire Magazine in the late seventies, Ken said in some interview that he just wrote a book about Harvey Weinstein, and he’s like, “Harvey is considered evil.” He’s like, “Roy Cohn is by far worse than Harvey Weinstein ever was.” That’s how bad Roy was in terms of his just complete lack of any kind of moral character. I was like, if that person feels that Trump is betraying him, what does that say about Trump? So I thought it was a really good kind of contrasting, if the audience could feel some small bit of sympathy or empathy for Roy, it would really make them think like, wow, Roy’s bad, but look at this guy. And so I thought that that was enough sort of the building blocks that you could build a feature around.

And then the other thing I wanted to say is that if you look on YouTube, some of Trump’s earliest interviews, there’s a famous one he did with the TV personality, Rona Barrett. And if you watch him, he’s soft-spoken, he’s unsure of himself. He’s actually semi articulate. And I was like, wow, how did that guy become this guy? And so I thought, let’s meet Trump in the first act of the film when he doesn’t sound like a raving lunatic, right? He’s quiet, he’s charming, he’s trying to be personable. And I think since Sebastian Stan, who plays Trump in the film, does this incredible sort of slow motion transformation. But I thought introducing Trump in a way that audiences didn’t expect could be really interesting because it would force people to lean in and be like, well, that’s not the person I know. And then by the end of the film, he’s much more fully formed person. He’s starting to resemble the person we see today. He’s not fully there yet, but he’s on his way.

Greg Iwinski: I think the whole movie is so interesting, especially as someone who I felt a lot of us who are doing political comedy writing and stuff like that, you know Trump so well now. You know his moves his speech pattern, he’s always going to do this. He’s going to do the story. He’s not hard to guess because he has, it’s like he’s a small computer program where he’s just going to do these things and that helps lot because the humanity’s gone and the programming’s there. But then at the same time, a thing that’s really interesting is I grew up in Arizona. I think we’re about five years apart. So I was born in the eighties, grew up in Arizona, didn’t know Donald Trump existed until The Apprentice, the show came out. So all of this, so this whole movie, I mean the movie ends, I was like two years old in ’87. So it’s interesting that this is an era of time that I think there are a lot of people who maybe would be in an audience were not alive and didn’t know about Trump in.

So it creates this weird space where it’s like, I know him so well from 2001 to now, but this is a guy who I have never seen and I don’t have a historical reference for. So in doing it also, how did you research the fictionalization, the characterization? How did you pull that narrative together and how much did you worry about having to have to have sources or have to have [inaudible 00:21:43]-

Gabe Sherman: Yeah, I mean, I would say the movie is inspired by true events, but it’s clearly fiction. It’s not a documentary. I just want to make that very clear. That said, all of the real flashpoint scenes in the film are based on things that there is historical record for that happened. And the main thing I ended up obviously beyond dramatizing dialogue that I wasn’t in the room to hear, the main thing I had to do to tell a concise two-hour tight feature is just compress time. So some events were just moved closer together in time for dramatic purposes, but not like inventing whole cloth. I felt like I wanted to capture, there was several things I wanted to capture that just how weird, it’s Tim Walz kind of coined the word for this election cycle, but there is something really weird about the world that Trump comes out of.

He grows up in this kind of Archie Bunker, white grievance culture of Queens where they live in this upper middle class enclave surrounded by communities of color, but it’s very segregated. His dad is famously a racist, was sued by the Justice Department for not renting apartments to Black people. So this is sort of the stew that Trump was marinating in. And then he meets Roy Cohn at Le Club, which at the time was the most famous nightclub in the city in the early-1970s. And if you just change the names, you took Trump out of it, took Cohn out of it, and you’re like the middle son of a middle-class housing developer in Queens talks his way into the hottest nightclub and meets this closeted gay mob lawyer who collects porcelain frogs, is permanently bronzed and takes him under his wing. And basically it’s like Pygmalion.

It’s just a really weird story. And so I thought taking Trump out of it’s a movie. I mean, there is a movie in that. It reminds me of a little bit like A Face in the Crowd, one of these stories where somebody is plucked from relative obscurity and suddenly becomes consumed by their own ego. So that was what I wanted to capture. I wanted the film to evoke how weird and Trump came out of this really kind of strange circumstance of events. And there’s a scene that’s not in the film that was in an early draft of the script, but I also wanted the movie to have a little bit of a genre feel, a little horror movie feel to it, because New York in the seventies was just like, I mean obviously wasn’t, I was born in ’79, so I didn’t live it, but from all of my research and interviews and the city was a hellscape.

And there was this scene I read in a book about Trump’s development of the Commodore Hotel, which was this first major development. And so he had to basically demolition, the old Commodore hotel was crumbling down and he built the Hyatt on its place. And when they were doing the demo of the Commodore Hotel, they found these giant super mutant size rats. And it was two dangerous, the workers couldn’t go in there to do the work. So the solution, the foreman’s solution was like they went to the shelter and got a whole bunch of feral cats and they released the cats into the hotel. And they heard a bunch of squeals and they shined a spotlight and they saw the rats were eating the cats.

Greg Iwinski: Wow.

Gabe Sherman: And then the coda to that scene is then their solution was that they went and got toxic gas and they just gassed the place and just asphyxiated all the rats. But this image of these mutant rats eating cats, the reverse, I was so haunted by it. And this was the hotel that Trump was developing. It’s so dark. And that image, I think I wanted the movie to, even though it’s not in the film, that image was in my mind as I was writing the movie.

Greg Iwinski: Yeah, it’s funny you talk about A Face in the Crowd, I think about being there a lot.

Gabe Sherman: Yeah, being there. Exactly.

Greg Iwinski: A lot with-

Gabe Sherman: Yeah, of course. Hal Ashby, I feel is such an underrated filmmaker. It’s like his movies were, I feel like he should be in the Sidney Lumet category. So good.

Greg Iwinski: I think about the opening scene that you have in the final version of this movie, and when you’re talking about the narrative and the whatever, and it’s interesting because it is a very sympathetic Trump in the opening scene. Because it is not the guy who wanted the Central Park Five to get killed, or the guy who was happily being racist in the newspaper or any of those things. It’s like a kid whose dad sent him to collect the rent and people are being mean to him, so it makes him low status and all these things. But it was interesting because it’s like this is the Trump at the bottom of the ladder.

I think about that story of Don Jr. goes to a Yankees game with him, and when he’s wearing the jersey, Trump slaps his son in the face and makes him wear a suit, and you’re just this abused and not at the top yet. And it was interesting. So is that kind of with all these characters, I was very surprised at the humanity that endeared sympathy with them. And is that a choice for storytelling purposes? Is it a way to just look at them differently because yeah, you talk about with Roy Cohn, like I’m sitting there feeling sad for him at this party, then I’m like, this guy sent two people to the death chamber in peace time.

Gabe Sherman: I know.

Greg Iwinski: He sucks.

Gabe Sherman: I know.

Greg Iwinski: Why?

Gabe Sherman: Even worse than that, he manipulated the judge. He broke so much legal precedent and rules, so many rules to get Judge Kaufman to send the Rosenbergs to the chair. I mean, if that had ever come out in real time, there would’ve been a mistrial. So yeah, no, he’s… I guess so, yeah, I mean there’s two things. There’s the storytelling aspect of it is that you need a character to go on a journey. When I sit down to write, I like to, one of the engines of drama is change. So I think of where does the character start and where are they going to end up? And within the bounds of reality, you try to put those things as far apart as possible. That said, Trump, the portrayal of Trump in those early scenes is somewhat as best as I can tell from my interviews and my research, how I imagined him to be.

He was miserable working for his dad in Queens and Avenue Z, way out by Coney Island. He had always been lobbying his dad to try to start developing buildings in New York, in Manhattan. And his dad was kind of this provincial, he was the quintessential big fish in the small pond. He was like a King of Queens, but didn’t have any connections in Manhattan. Donald felt stifled by his dad, Fred Trump, and that he did collect rent. I read some interview that Trump gave in the eighties that he said when he was collecting rent, one of the things you did is if there was a difficult tenant, you would knock on the door and then stand to the side because they might throw hot oil or water at you. And so that image in my mind is actually a scene I put in the movie. I just mean that’s a reality of Trump’s background that we don’t necessarily associate with him today.

Greg Iwinski: Which is such a funny advice thing too, like, well, if you’re not running a slum, they’re not going to throw hot water at you.

Gabe Sherman: I know, exactly.

Greg Iwinski: But that’s not an option for the Trumps, so they just get out of the way.

Gabe Sherman: And then the other thing that stuck with me is one of the executives for the railroad. So the Penn Central Railroad owned the Commodore Hotel at the time, and they were talking to developers about selling it. The railroad was bankrupt. They were selling off all their buildings and assets. If you think about Trump at the time was 27, I think, when he started developing the Commodore. How did he get the contract to do that over all the other builders?

And the executive at the Penn Central Company gave some interviewer where he said that Donald was relentless and just would want to spend time with him and talk and ask his advice. There was a charming, there was an earnestness and a hunger to him that I felt, again, was very different than today’s the most cynical kind of nihilist person that you could imagine. But back then, that hunger to do something actually, I thought was a really interesting way to introduce the character. Because if the character has a goal, no matter what the goal is, if it feels true to them, the audience is going to want to be like, okay, let’s see if they can do it.

Greg Iwinski: I think that’s something that’s interesting about, again, this is because I think all of us who’ve stared at him for so long can characterize this guy and you can lay out who you think he is. So it’s like this window into your experience having met him as well, who he is. And it is kind of like it’s if we’re all watching the Jets offense and we’re all talking about how we think it should be run. So I really enjoyed and appreciated it from that side as well is like, you know-

Gabe Sherman: No, I think that was one of the challenges of this project.

Greg Iwinski: You’re writing about the most famous [inaudible 00:30:41] person in the world-

Gabe Sherman: I can’t tell how many, every, not only just screenwriter friends of mine, but relatives and strangers on the street, when they ask what I’m working on, everyone has an opinion about it. I can’t tell you how many times I heard people say, “No one wants to watch a movie about Donald Trump. That’s stupid. Terrible idea.” And so I had to just kind of put blinders on and not listen to any of that and just try to write a character that felt true to me.

Greg Iwinski: I think what’s interesting about this character is when you were talking about desire and motivation is if I’m reading, what you’re doing is he has no interior life. So at the end, “What is the point of you doing all this, Donald?” It’s like, “To do it.” It’s a shark. The only reason to swim is to keep swimming. So he goes on this exterior journey, but the interior journey, it’s just a flat line of I want to do things, I keep doing things I want to do.

Gabe Sherman: I would clarify that slightly. It’s not only is it a flat line, I think it’s a emptying out of any humanity that existed at the beginning. I think throughout the movie I tried to have these signposts of moments where you start to see him becoming a shell of a person. So I use the relationship with his brother, his older brother, Freddy.

Greg Iwinski: Yeah, I thought of that because when he talks about when Freddy died, “You can cherish life more or it can cheapen life. And for me, it cheapened it.” And I’m thinking of that quote in that Sebastian Stan, he’s so good in that moment, crying and then kind of turning off.

Gabe Sherman: Turning off. And what I wrote in an earlier draft of the script, one of the stage direction notes was like it was one of the last human feelings he felt, in that moment. It’s like I wanted, after that scene, he just closed off anything. His heart was completely stone at that point. So yeah, so Freddy, the arc of his relationship with Freddy I think was a barometer of Trump losing his humanity. And also his relationship with Ivana, which culminates in a violent sexual assault. And I think that allows the audience to see what his quest for power is doing to his soul. But in terms of what his goals are, his goals were the same. But to achieve his goal, he had to basically just decide to stop being human.

Greg Iwinski: Yeah. It becomes the machine, and I think you see him move towards that. This is less about, this movie ends at Art of the Deal, which is late eighties. And then I think there’s this other phase where you get to the reinvention like you talked about. And this is just two people who’ve had to look at Trump a lot that I’m asking this, but do you think that, is there another great change from Art of the Deal to, or is this the guy we see at the end of this movie, is who we’re seeing now? Or is there another big turn that happens?

Gabe Sherman: That’s a great question. I would say the biggest change is that, so the movie ends in late eighties, I guess ’86, ’87, events have been moved. There’s a scene, there’s a really crucial scene at the end of the movie when Trump’s bankers are on his ass and he’s behind on his loan payments, and he goes to his dad who’s suffering from Alzheimer’s and is totally out of it. And he basically tries to swindle his father into giving him control of the family trust so that he could then borrow against it to pay… Which actually did happen in 1999 and around 2000, there was this huge family fight between Donald and his siblings because he did go to his dad, Fred Trump, who did have Alzheimer’s at the time and try to finagle his way into controlling the trust. I moved that event 10 years earlier because I felt like that was such a perfect way to show what Donald was capable of that time.

But I guess to your answer of was there another change, I would think the major change that happened post the end of the movie is that Trump stopped, he became a character of himself. He stopped doing business and started playing a businessman. He became a media creation. The Art of the Deal catapulted him into national prominence, and he became much more of a media figure than a businessman. He stopped really building. I think one of the things I was thinking about in writing this movie is if he had stopped after Trump Tower and just kind of even rested on his laurels, he would been considered a very successful builder.

The Hyatt and Trump Tower were two projects that were really risky, and everyone thought it was going to fail, and he pulled them off. And so everything post-’87, his bankruptcy, the casinos, he just started licensing his name. He just was sort of just playing the character of Donald Trump rather than actually doing real deals. I mean, he could say he did deals, but I think that was the biggest change I saw is that it was sort of the end of his time as an actual developer.

Greg Iwinski: He becomes a brand at that point.

Gabe Sherman: A brand, exactly.

Greg Iwinski: Yeah, a living brand. It’s very interesting. Now, I’ve written a lot of political comedy, and I’ve also been told by some very nice people in our government places I shouldn’t go because of the political comedy I’ve done. You’re writing about very powerful, not just him, but also Ailes, and they’re coming after you and doing this. How do you, not that I’m thinking you’re like, “I can’t do this.”, but how do you fold that into your life going, these are the stories I’m telling, this is the cost I’m going to pay.

Gabe Sherman: Yeah. It’s hard, because something about these characters that I might intensely disagree with their politics or the way they treat people, I have this deep curiosity about, it’s just fascinating to me that people go through the world acting like this. It’s like, okay, how does that work? But with the Ailes book, I got death threats. We had to go, there was one time where Breitbart wrote an article that called me like a George Soros attack dog, and put me on the front page of the website. And started getting insane phone calls and had to go down to my in-Law’s house in Pennsylvania just to chill out for a while. So yeah, I mean, when you’re in the middle of it, you’re like, holy shit, is this worth it? And then that passed, and I don’t know, maybe it’s misplaced, but I’ve enough faith in America that we’re not Russia, artists can speak their mind and they don’t face physical harm. But I don’t know, I just feel these stories are really important to tell.

And also from a place of the movie is not, and think maybe you’ll disagree or I’d love to hear your take. It’s not a movie that’s telling you how to vote. I bet MAGA people could watch this movie and parts of it, “Yeah, he’s my guy.” Things that I might find appalling. It’s like a Rorschach test, other people might find that’s why they like him. And so I also wanted to try to write this movie in a way that took it out of the left-right schema of discourse, because it’s not a liberal movie. It’s not a conservative movie. It’s trying to be a movie, a humanist movie that’s exploring him as a character. And Trump’s attack on the film, he hadn’t seen it at Cannes. Obviously, he hadn’t seen it when he launched his attack at Cannes, was immediately trying to push this movie into the realm of politics.

And I’ve been trying to do my part and the actors as well, when we’re talking about the movie, is to take it out of the realm of politics and try to talk about it as art. Because then it’s not, I don’t want this movie to be like, oh, this is just liberal Hollywood, because it wasn’t. Ali Abbasi, the filmmaker who made the movie is a Danish-Iranian citizen. He’s not in our system. He wanted to make a movie that held up a mirror to the system. So yeah, I guess that’s circling back to your question about do you feel threatened writing these stories? I guess I don’t, because I try to write them as just stories. And unfortunately, the subjects of the stories then take that as an attack, but that’s not the intention.

Greg Iwinski: Yeah. Well, I think when you’re talking about political figures too, it’s so much of what politics is controlling exactly how you’re perceived.

Gabe Sherman: Exactly.

Greg Iwinski: That’s what it is. The reason I walk out at the debate and do a handshake first, so I look strong. Everything is-

Gabe Sherman: Everything is choreographed.

Greg Iwinski: Everything is that. So then to have someone tell a story about you where you are not controlling it is very-

Gabe Sherman: His worst nightmare.

Greg Iwinski: And I think if you did this for any president or candidate-

Gabe Sherman: Yeah, I did a Barack Obama movie. They probably wouldn’t be happy about it. Yeah.

Greg Iwinski: It’s like, “He’s smoking too much. Don’t show that.” But when you’re talking about showing him, it is one of the interesting things about him, because this movie is, it is apolitical in the way that this Trump has no beliefs. In the sense that political beliefs, he’s not sitting there being like, tax rates should be this or we should do this with [inaudible 00:39:20]. It’s like, “I like big strong things. I don’t like weak things.”

Gabe Sherman: Yeah. He did have one belief that was pretty consistent from the seventies and eighties was this idea of America getting ripped off.

Greg Iwinski: Yes.

Gabe Sherman: That was, I did, when I saw the Rona Barrett interview from, I think it was ’81, ’79, ’80, I was really struck by that because he was obviously nowhere near the political world at the time, and yet he was talking about the country getting ripped off by other people. And you could just cut and paste that to today. So I thought this idea of people taking from him, there definitely is white grievance undercurrent to that of welfare people taking too many things from his class. But the idea of America itself being ripped off, I thought was the one part of his kind of worldview that has stayed consistent.

Greg Iwinski: Yeah. And underneath that, “If I was in charge, we wouldn’t be getting ripped off.” And you can see in the film people being like, “Well, you’re going to run for president?” It’s like, “I don’t know.” Yeah. I think in the sense that looking at this Trump in a way that is, there are things that in my understanding of I believing that the sexism and the racism and some of these miserable things are baked into who he is and has always been. But this movie is in this context of this business guy who then gets drawn in by the worst person possible and then adopts all of this because I mean, Cohn is saying a bunch of racist, crazy stuff in the movie-

Gabe Sherman: Yeah, of course.

Greg Iwinski: But that Trump is sucked up into this larger thing. But I was talking about it earlier with my wife about this film, which is in the way this film is built is like there’s so many aspiring businessmen in this city who could have gone on the same path or might have gone on the same path. They don’t have the talent or the skill or the demagoguery that Trump has. He’s so good. I mean, we talk about it all the time. Trump is good at being funny.

Gabe Sherman: Yeah, he’s an insult comic.

Greg Iwinski: And I wish that so many friends and probably people we both know who get so mad about him. Look, I’m a Black American in an interracial marriage. I’m very at risk, but he’s funny when he’s doing the Abdul, I sent you a picture of your house.

Gabe Sherman: Yeah. Why, first of all, who’s Abdul?

Greg Iwinski: And you don’t need to know.

Gabe Sherman: It’s so great.

Greg Iwinski: But that’s a joke.

Gabe Sherman: Exactly. And I feel like that’s what I try to write is there’s parts of him that are like, you can disagree and be offended by it, but it is legitimately, you have to take it on its own terms. It’s funny.

Greg Iwinski: Yeah. There’s a reason that he can be so bad and still be in so many rooms, and it’s because he is at some point entertaining and [inaudible 00:41:50]-

Gabe Sherman: And his social observations of people are, and he’s done this with me when I’ve spent time with him, his ability to laser in on somebody, their weakness or their flaw or their neuroses. He’s like a laser into your soul. There was a time when I was at New York Magazine, it was during the campaign. He was going to do a rally at his golf course in Miami, Doral, and I was flying down to cover it for the magazine, and I was on the phone with his then press secretary, Hope Hicks. I was just trying to do logistics planning, like, “All right, I’m coming down to cover the rally. Is it Friday night?” Blah, blah, blah. And I could hear Trump in the background in the office being like, “Gabe, I’ll give you a room at the hotel. Just come down, stay at the hotel. I’ll comp it.”

And I’m like, “I can’t take a free room from the candidate I’m writing it. I mean, it’s a total breach of journalistic rules.” I’m like, “No, I can’t do that.” And I could hear him saying in the background, “Gabe, don’t be a baby. Baby Gaby.” And did zero in on there is a part of me that is a rule follower, and doesn’t want to, and he picked up on that. And so I can respect that talent, even though I find it very disturbing.

Greg Iwinski: He has a superpower that he uses for the worst possible outcomes, but it is what it is.

Gabe Sherman: Have you seen the Darth Vader mashup?

Greg Iwinski: Oh, no.

Gabe Sherman: There is a great one where it’s just the scenes from Star Wars, but instead of Vader’s voice, it’s just Trump saying Trump things. And I mean, it’s hysterical. I mean, you have to laugh at it because we’re living in it.

Greg Iwinski: Yeah. We are, I don’t know now, you’re looking at this character now, I think you could probably write a whole nother film about even post-2016 Trump, which is you went from this peak height of his powers and then seeing it now. It always shocks me now to go back and watch 2016 and realize, oh, eight years is a long time. You really have changed.

Gabe Sherman: He’s declined.

Greg Iwinski: Yeah, he’s doing some standup from two albums ago. You’re kind of like, I’ve heard this too many times.

Gabe Sherman: The other thing I think I wanted the film to do, just in this vein of finding parts of Trump to be very entertaining, is I wanted the audience to be drawn in and go on this ride with this character and then suddenly get to a point in the movie past the midpoint where it stops being really funny at all, and it becomes very, gets just much darker. And then at the end of the movie, it gets just really disturbing. And it’s almost like becomes, again, like I said, a genre movie at the very end.

I thought that was a great emotional place to leave the audience because I mean, we all felt this in 2015 when Trump ran for president, right? “Oh, he’s just doing this for ratings. He’s harmless. He’s just trying to get back on The Apprentice.” We obviously learned that we should take him very, he does what he says he’s going to do. And so I thought leaving the audience with that feeling of like, wow, okay, this is very upsetting. I thought was trying to capture my experience of covering Trump, of being kind of entertained by it at first and then really disturbed by it.

Greg Iwinski: I think there is, we all have friends or we had friends in high school who were kind of bullies and kind of dumb, but kind of popular. And if that’s all they do, that’s fine, but if they become the governor of your state, that’s very scary. And when he is not president, he’s just the blowhard. But when he is president, he’s terrifying. I think the choice at the end, I mean when you’re talking about going into genre, it is very, I wrote down Body Horror, just that surgery scene and that stuff. And I think what that does come across is that when you see him at the end with the red tie finally, it’s like, oh, this is the transformation to the God.

Gabe Sherman: Exactly. Like the Darth Vader scene, right?

Greg Iwinski: He’s literally physically and spiritually and everything changed himself.

Gabe Sherman: We wanted that, again, spoiler alert, so I hope listeners of the-

Greg Iwinski: Yeah, we will say at the front, all spoil-

Gabe Sherman: Yeah, see the movie. Please, please see the movie before we listen to this. But we wanted to hold back that version of Trump to the very end, because that’s sort of the Franken, that’s the monster is then that final transformation is now he’s Trump. He’s younger, but he is the guy that we’re going to get to know later. And so Sebastian really withheld his performance and did a very restrained version of Trump really into that vast scene, and I feel like he earned that moment to then just go full with the hands.

Greg Iwinski: He has a couple of times in the movie where I heard it and it yanked me where I was like, yep, that’s it. That’s it. Yeah. That transformation thing is so odd, and again, this is an odd to Trump person tangent, but with the red tie thing, it becomes a hallmark that you almost don’t even notice. I only recognize it again because at the September 11th thing. JD Vance is also wearing a red tie, and they’re the only two guys wearing red ties, and it’s like you’re watching this little Cohn, Trump thing happen again, just with a less talented underling.

Gabe Sherman: The other thing, this isn’t in the movie, but it’s something that I’ve been struck by when I’ve read interviews with Trump, is he also, he loves cinema. Sunset Boulevard is one of his favorite films. Citizen Kane is like, he’s gone with the, I mean, he loves classic old Hollywood. But I think he thinks visually, part of what makes him so successful as a communicator is that he speaks in visual language like that we sang with Abdul, right? You can imagine him talking to a guy named Abdul, “Here’s your house. We’re going to blow it up.” He thinks in visual terms, in kind of cinematic terms, and I think the red tie, the imagery. If you watch his rallies, he’s always flanked by very bright, many red, white and blue flags. He’s somebody that is, or even the response to the assassination attempt in Pennsylvania getting up and doing the fist pump and saying fight. He knew in that moment that this was a made for [inaudible 00:47:46], he was an action hero.

Greg Iwinski: That was generational showmanship to go, I just got shot. This is going to look great. And to think of that, and that is, take the moral part out of it, admirable-

Gabe Sherman: Impressive.

Greg Iwinski: … to be that fast.

Gabe Sherman: Yeah. No, I mean, that’s where, again, I think you mentioned there were other businessmen in New York in the eighties who were hustlers, but that kind of talent can’t be taught. I mean, there’s something innate in his character that makes him able to do these things that most people would be like, “Holy shit, get me out of here. I’ve been shot.”

Greg Iwinski: Which also gives me a small bit of comfort about the future, is that there’s not someone that talented.

Gabe Sherman: No, he’s [inaudible 00:48:25] generous. I mean, you saw every politician who has tried to basically be a mini Trump is completely blown up. DeSantis, even JD Vance.

Greg Iwinski: Yeah, because they’re not funny. They’re not charming.

Gabe Sherman: They’re not original. Ted Cruz, all these guys, they just come off as totally phonies. And so yes, I think Trump occupies this sort of completely original place in American life. I mean, there might be a different Trump, it could be scary in a different way. But no, I don’t think anyone can fit, can sort of take over the MAGA base that he is.

Greg Iwinski: Yeah. I do want to ask, and don’t give away anything upcoming, and I don’t want you to blow anything, but if you were going to write another film about a big evil figure, doesn’t have to be from now, it doesn’t have to be whatever, but maybe one that you know can’t make, but you’d love to make. Who would you make a film about next?

Gabe Sherman: Oh God, that’s a big question. I don’t have the answer. And that’s not because I’m being coy that I have a script that’s in my drawer that I’m hiding. I don’t have the answer, but I know how I’ll find the answer, which is that I have to wake up thinking about the character every day, wanting to spend time with that person and explore and understand. And if I don’t feel that obsessiveness about the character, then I don’t want to write it. I won’t be able to write something true. So Ailes and Trump are sort of two examples of characters that very malevolent people, but every day I would just wanted to be how, this shouldn’t be happening. Somebody shouldn’t be able to get away with this many things, and yet they keep doing it, and how does that work? So I’ll find that person. That said, to any producers who are listening, that’s not my only creative outlet.

Greg Iwinski: They love the writer thing. I will write other stuff.

Gabe Sherman: I mean, I have projects with much more uplifting main characters that I’m working on. But yes, I know even regardless of the character, whether pro or con, I have to feel some sort of obsessive connection to them.

Greg Iwinski: Because then when you’re writing and you’re stuck or you’re sitting there with, that’s what spurs you to keep digging.

Gabe Sherman: Yeah. Then it’s just a yoke around your neck and you’re going to just be suffering. So if you actually want to do it, then you’re going to push through that.

Greg Iwinski: Yeah. Most helpful thing with writing is wanting to do.

Gabe Sherman: Wanting to do it. Not eating the muffin.

Greg Iwinski: Yeah.

Gabe Sherman: Yeah.

Greg Iwinski: Gabe, thank you so much for coming by.

Gabe Sherman: Thanks Greg. All right. Be well.

Greg Iwinski: OnWriting is a production of the Writers Guild of America East. The series is produced by WGAE staff members, Jason Gordon, Tiana Timmerberg, and Molly Beer. Production, mix and original music are by Taylor Bradshaw. To learn more about the Writers Guild of America East, visit us online at wgaeast.org or follow the guild on all social media platforms @WGAEast. If you enjoyed the podcast, please subscribe and give us a five star rating. Thanks for listening. Until next time. Right on.