The Press Box - Instant Reactions to the Tim Walz–JD Vance Debate With Semafor’s Benjy Sarlin. Plus: Gabriel Sherman on Writing 'The Apprentice.'

Episode Date: October 2, 2024

Hello, media consumers! In a special bonus edition of The Press Box, Bryan has two guests. First, he speaks with Semafor’s Benjy Sarlin for instant reactions to the Tim Walz–JD Vance vice presidential debate. They discuss the following: The biggest surprise of the debate (1:22) Who looked more confident, Tim Walz or JD Vance (9:35) The January 6 exchange (16:40 Whether or not this will be the last debate (26:04) Then he speaks with screenwriter Gabriel Sherman about writing 'The Apprentice,' a story about Donald Trump (30:44). He discusses the following about the film: How he went about writing the story (31:10) Trump’s relationship with Roy Cohn (32:36) How Cohn’s rules of winning influenced Trump (37:04) Deciding on Sebastian Stan to play Trump (47:02) Hosts: Bryan Curtis Guests: Benjy Sarlin and Gabriel Sherman Producer: Brian H. Waters Learn more about your ad choices. Visit podcastchoices.com/adchoices

Hi, I'm Tara Palmeri. I'm Puck Senior Political Correspondent and host of Somebody's Got to win. Brought to you by The Ringer and Spotify. The 2024 election has been upended with Joe Biden off the ticket and Donald Trump facing a new challenger, Kamala Harris. If you want to hear what the insiders are really saying about the race, join me Tuesdays and Thursdays as I break it all down with lawmakers, journalists, and political strategists.

We'll go deeper than the headlines to the anxieties at the highest levels of power. And of course, we'll chew over all the high. hot political gossip as we head into this historic election. Be sure to follow, somebody's got to win at Spotify or wherever you get your podcasts. Hello, media and consumers. Welcome to Pressbox. Brian Curtis of the Ringer here, along with producer Brian Waters. Coming up in just a few minutes, we're going to bring on reporter Gabriel Sherman to talk about writing the screenplay for the new Trump movie, The Apprentice. But first, we got to talk about last night's debate between Tim Walls and J.D. Vance. And here.

to offer us his scorecard is the man who is semaphore's Washington Bureau Chief. He is this podcast's official politics reactor. Benji Sarlin, welcome back to the press box. Thanks for having me, Brian. Always good to be here as the official politics reactor. So, Mr. Reactor, what did you think about last night? Well, there was a lot to react to. It was a fascinating debate. It seemed to take place in some ways in a time before Donald Trump, which was much commented on during and after the debate. You had two candidates who were, for the most part, performing pretty well, getting pretty far into the policy weeds on some of these issues, obviously with plenty of fact check potential for both of them at points, but still generally a recognizable policy debate.

And the big surprise was being quite civil to each other, often talking about all the ways they agreed and referring to each other somewhat warmly. These are two candidates who have said horrible things about each other for the last two months. I mean, part of the reason Tim Walls was even chosen was that he was this attack dog on weirdos like J.D. Vance. And obviously, Vance they've used as a pretty much as a pit bull since the moment they chose him on the Trump side. So it was very fascinating to see a very friendly, civil kind of Midwest, nice debate that stuck to the actual issues. Veteran debate watchers will remember the Joe Lieberman Dick Cheney vice presidential debate from 2000, which had a very, very similar vibe to this.

And that was clearly part of J.D. Vance's plan going into last night, do you think? Yeah, it was interesting to see where each candidate was kind of coming from before this. So J.D. Vance, the single most important thing about J.D. Vance going to this debate was that he was monstrously unpopular. Pretty much his introduction as a vice presidential candidate just could not have gone much worse. He got defined by this childless cat lady's riff that he'd given repeatedly before, basically the first week, and never recovered. He's been of the four candidates when you poll just basic, do you have a favorable or unfavorable impression? He is consistently the worst. Walls being the opposite.

He usually polls the best among the four. So you had Vance coming in from this position where he was generally seen as pretty unlikable, but also that doesn't mean unhelpful to the Trump ticket. He's done the most interviews of anyone. They just decided, all right, no one's going to like this guy, so we'll just use him as the attack dog, as we mentioned, to just drive home the most negative messages against walls, against Harris, to just blanket the airwaves doing as many interviews as he can to get our message out. So, you know, to some degree he's been effective even while being somewhat unpopular. But this debate, he took an interesting turn.

He sanded off all those rough edges, and he presented friendly Yale law degree, pundit, J.D. Vance, who knows how to speak to college-educated America, and who knows how to stay away from some of the tougher MAGA points. And something that's interesting here is, you know, this is the J.D. Vance that became famous. It's easy to forget, which is J.D. Vance became famous explaining why Trump was happening to NPR listening liberals. That is his claim to fame. He did not start out as some populist conservative figure. He started out primarily as someone who was beloved, you know, not exclusively in liberal America, but well known within liberal America. And in fact, part of what the Trump world loves about him so much is he has that.

that kind of traitor to his class vibe of the person who's gone the other direction and embraced Trump when so many people in his cohort have just become more and more opposed to him. So I thought it was interesting that he kind of reverted back to that form. You know, people forget that Vance can speak to that audience in that language. And I think that's what he was doing from the start. So fascinating. Because from that very first question, which was about Iran and Israel, he stops and he looks at the camera and says, I'm going to introduce myself to America.

talk about my goals for this evening. Throughout the debate, he talks about his upbringing. He talks about his kids. When they get a question about climate change, which is a bad issue for Trump in Vance, he starts off expressing sympathy to the victims of Hurricane Haleen. There's that moment when they were talking about school shootings, and he says, Governor Walls, I'm sorry your son witnessed a shooting at a community center.

Christ have mercy. So if part of debate strategy is having a debate on your preferred terms, even your preferred terms tonally speaking, this was clearly the debate that J.D. Vance wanted to have. And as you say, it got rid of his worst or neutralized his worst quality, which is his unlikeability, and also maybe helped at least ameliorate Trump's worst quality, which is that he was an agent of chaos when he was president.

Yeah, and it's interesting how that played out. I mean, having Vance there, you saw, I think what they had in mind when they picked him initially. was again kind of a version of the old J.D. Vance, someone who could explain MAGA to people who are more skeptical and stylistically don't like it as much. And it hasn't worked out much to this point. But here you saw its potential, right? Which is he tried not to get in the weeds on the things that bother people most about Donald Trump and stick mostly to this very broad frame of, look, we all know about Donald Trump. You all can remember whatever your least favorite moment is or least favorite tweet is, but just think back to that time.

Weren't things better? And you just kept referring back to this period. You know, you said at one point he said Tim Walls was stuck playing whackamol trying to convince people that things weren't better in the Trump era, you know, pre-COVID that like, oh, you can say whatever you want, but you have to justify why wages were growing, why unemployment was low, why we didn't have, you know,

a million wars breaking out all over the place. It was all trying to keep this one very simple frame for the audience. Things were better back then. Look at me. You can see perhaps a less. chaotic version of Trumpism to reassure you. The flip side of that, which I saw several people bring up, is that I don't think this debate's going to matter that much, but there is kind of an interesting meta frame here, which is I think some people are watching this and thinking,

wow, I forgot how nice politics was before Trump. And that's not necessarily a great thought for Vance to get across either, you know, necessarily. If you're watching this and thinking like, wow, it can look like an episode of the West Wing, I think you could feel pretty confident. going to look like that if Trump wins. You're not going to be seeing Vance every day. Is it as simple as saying Tim Walls was nervous last night? Yeah. And it's funny. There's always this pre-spin of expectations. So there was a big story out. I think it was CNN. Sorry if I'm wrong to whichever outlet did it on how on how Walls was preparing for his debate and was indeed very nervous and worried about

letting people down and worried about speaking too fast and being defensive. And then it turns out it wasn't really spin. All those things happened in some fashion or another, especially in the beginning he seemed very nervous. There were times where he mangled his words a little bit. He seemed in a bit of a rush. On the other hand, this was not necessarily like a terrible debate

for him on the merits either. Especially on a topic where he is less familiar with or acquainted with the dressing in detail, the first one mainly, which is kind of a weird question, I have to say, basically like, would

Obama ran for the most part, which is not something a running mate is going to answer on a debate stage. But, you know, he seemed a little more uncomfortable with that. He was finding his footing. Where he did do better was on the topics where he has been most prepared and most comfortable talking about Republicans, abortion, healthcare, and then probably the biggest moment of the debate at the very end, January 6th. So it was clear he was nervous. He did not look nearly as confident as J.D. Vance, who looked happier to be on that stage than I think like he's ever been anywhere in his life. But it wasn't like a meltdown performance either. He had some moments that the campaign will be clipping and, you know, potentially sharing. There's already one they've turned into an ad, which is the January 6 exchange. Yeah. And it's not just a matter of nervousness. It's that his superpower, Walses, is connecting with people, looking into a camera or looking out over an audience and being someone who people can not.

along with and say, yeah, this guy's making a lot of sense. And I thought his nerves last night really sap that quality a lot. As you say, he got more comfortable as the debate went on. The topics became more friendly to him. The first five topics were Iran, climate change, immigration, the economy, and leadership qualities, which was devoted to his claim about being in China during Tiananmen Square. So those were not great topics for him. Those are also the breaks. That's what you have to do. You've got to answer the questions. But it just took him a wild get his footing. And then when he did, as you say, his strongest answer was the last one about Jan 6th. Then he gives his closing statement and looks into the camera like, oh, this is the Tim Walls

that appeared at the DNC. He was just a much, much more effective communicator. Yeah. And, you know, not to get too into the media weeds, though on this podcast, I guess we can. There's been this other interesting meta story going on around Walls, which is, like you said, the thing that Walls was known for, the reason he was picked is that he was picked, is that he, he's seen as this great communicator to the average Joe. He speaks in language people can understand. He's knowledgeable. He's experienced.

And he comes off just very well. He comes off likable. He comes off as relatable. So one of the weird things of the last few weeks is that Walz has not been doing a lot of media. Hasn't been doing a lot of interviews. Vance has been doing dozens of interviews, like just an incredible amount of them. They haven't all gone well for them. They often, you know, the clip that travels is often him like arguing over who's eating pets and stuff and getting fact checked.

It's not like they've necessarily always been helpful. But he is just getting a lot of reps in, as they say, you know, including on topics that are less favorable to him and tough questions. And, you know, getting asked about some of his worst things that he said on a right wing podcast, you know, 10 years ago. Or, you know, getting asked about some of the more aggressive fact checks, like we said, like the pet eating stuff in Ohio. Walls hasn't been doing that, and I wonder if that showed a little bit, that they maybe made a mistake, not giving Walls, who, again, they chose because he is supposed to be likable, relatable, you know, good at conveying the campaign's message. He was doing lots of interviews before he was chosen as the running mate. That's partly how he got the job. You wonder if they made a mistake keeping him away from some of the more extensive national interviews in which he might have at least dealt with some of these issues, like his, you know, somewhat serial habit of exaggerating earlier.

and test it out and been able to fine-tune the response and see if it worked or not. And also, you know, got rid of some of those nerves. You know, say he did the Sunday shows like Vance did. Vance did almost all of them. He would have gotten some of these tough questions. They would have been on news of the day. They would have been on some more offbeat topics. He might have gotten a little more in the rhythm of, okay, I know how to do a Sunday show,

but now I'm more comfortable doing it on behalf of Kamala Harris, which I think is part of what tripped him up a little bit. you notice he kept relating everything back to Minnesota, which I thought was an interesting, like, at times I thought it was an effective move being like, look, we know the Harris agenda is going to work because we're doing something similar in my state and it's working. He came back to that many, many times. But it also reflected the fact that he doesn't have a lot of experience defending the Biden Harris, now Harris agenda. They seem to almost not refer to Biden at all in this kind of national setting. And I think he might have benefited from getting some more

practice. There were so many moments when Walls was talking about Minnesota and Vance was talking about his upbringing that it felt like a purple state Senate debate. We veered a little bit away from being your candidate surrogate on the national stage and we're talking about each other, which was a very interesting element of it. I totally agree with you about the crispness of walls and the practice of walls. There were just so many moments last night and I think if you look at what Democrats are saying, where they want to say, Boy, he just should have jumped on Vance a little bit more. I was thinking of Vance's answer about school shootings where he said,

we have to make the doors stronger, we've got to make the windows stronger, or Vance's notion that Trump, in fact, saved Obamacare instead of trying to sabotage and end Obamacare. Walls had answers to those questions in those two cases. He had fairly effective answers, but it wasn't that I'm hearing something that my opponent says, and then I am quoting it back to you and jumping on it

and telling you why he's wrong. And maybe if you get more reps on cable news, maybe you just have that a little bit more at your fingertips. Yeah, and the thing about it too is that the skill I think people liked from walls that they were missing here to some degree is that he has a way of just cutting through the bullshit and getting to the point. That's what the weird talk was all about. And that's what was kind of missing that I think they wanted,

which was in the healthcare answer, For example, Walls gave, in many ways, a great answer. He was going to this extremely substantive, nuanced policy discussion of why the Affordable Care Act was created, what problem it was addressing, how the Trump administration undermined it in certain ways, why the aspects of it that Vance has been talking about repealing would be harmful. In many ways, it was intelligent, it was smart, it was, we could debate how effective. but I think a lot of Democrats would have just preferred something that cut through the bullshit a little more was like, look, ignore all these $10 words that J.D. Vance is throwing out. Here's the simple story. Donald Trump tied to away, take away your health care, and he would do it again. You all remember this. We all saw it. There's no need to get in the weeds on this. That's what happened. It's like those are the kinds of answers that I feel like we're missing a little bit. And, you know, the thing he did not say that I think some Democrats would have loved to see is J.D. Vance is love. lying, you know he's lying, you know this kind of slick talking asshole, and you shouldn't listen to him. Which is, by the way, something J.D. Vance's prior debate opponents have tried on him. That was Tim Ryan's strategy when he was a Senate debater. And what they weren't getting that was they were,

what they were getting instead was very respectful disagreement. You know, my opponent has a point of view, but let me give you some facts and let me tell you a little about the policy. It was almost playing against type with walls too, which is that like, oh, these are very wonky answers. I agree. You know who was really good at tonally controlling a debate when he was vice president or a running mate was Joe Biden in 2008 with Sarah Palin and 2012 with Paul Ryan? He had a way of making an opponent debate him on the terms he wanted to debate on. And you could feel walls last night, whether he was doing well, whether he was doing poorly.

He just didn't feel like he had control of anything last night. He was reacting to J.D. Vance and almost. the opposite way that Kamala Harris was controlling her debate against Donald Trump. I didn't want to ask you about Jan 6th because that was an exchange. Lots of people are going to remember. That seemed to be, you know, the limits of how Vance could put a thumbs up emoji on the Trump years. What did you make of that question and then the back and forth between the candidate? I thought that was definitely the worst moment for Vance and the best moment for Walls.

Obviously, it's just an indefensible position. Trump is what he is. He did what he did. Voters have made clear they really do not like it, even as they are considering sending him back to the White House. And this was also one of those moments when you saw the limits of Vance's slickness, which is on a lot of those answers like health care, he was saying things that were somewhat absurd, this idea that Trump just fixed Obamacare or salvaged it out of the good of his heart and it was working better than ever because of Trump. I mean, that was. if you wanted to challenge him and pick apart that, it would have been very easy to do. It was kind of brazen. But if you aren't too familiar with what was going on there, it sounded pretty smart. You could appreciate on a debater's terms, you know, that he was finding ways to get around his tougher topics. But January 6 was when he just reverted to kind of like this really obnoxious whataboutism that I don't think has played well with people where it's, you know, only the

most red-pilled, you know, Elon Musk alert on your phone audience member is going to be like, well, I guess it's fair that, you know, Trump incited a coup attempt as part of a vast attempt legally and potentially illegal to, illegally to overturn a free and fair election. But he said something about censoring Facebook, and I guess that's the same thing. Like, no, you have to be so far already on his side to think that's a remotely compelling argument, or even to know what he's referencing. Like this is not a commonly discussed topic outside the right. It's mostly something they've come up with in kind of anti-anti-Trump circles to feel better about backing Donald Trump, which is a very narrow constituency.

So I think that was the one place where the whole Yale Law School, you know, debate champion approach just broke down a bit. You're defending the indefensible. And it was also where Walls was able to turn to him. First of all, if I remember that segment correctly, Vance was the one who wanted to keep talking during that segment. They did one exchange and then he raised his hand and say, I want to say more about this, which was a strange move because if you're J.D. Vance and the Trump ticket more broadly, you just want that segment to go away. It's at the end of the end of the end of the end of the end of J.D. Vance has to say, I'm focused on the future. Yeah, and it's interesting. And when we talk about the cut-through-the-b-b-s moments for Walls, that was the one time you saw it really effectively, which was the one point they wanted to convey, and that Democrats have been hoping he would convey he got in, which is, hey, remember Mike Pence? The only reason he's not here is this one issue. That's why you're here. And he managed to get that in simple terms without getting into the weeds about, you know, Jack Smith's case or the particulars of the electoral vote certification process in states. He didn't get won. on it. He just got to this, look, you know why Mike Pence isn't here. Remember what happened. I thought that was effective.

Did you make the snap polls last night? They were all very close. CNN, 51 Vance, 49 walls, CBS, 42 Vance, 41 walls, Politico's poll had it 50-50. How do you read those? It's so funny because it looks like every poll of Pennsylvania and North Carolina right now, it seems like we cannot escape these like inside the margin of the error of one or two point leads. but they were very interesting. So one is that it was not entirely surprising to me that Walls came out about even, even though Vance was on points on the theater criticism,

getting all these plaudits. This is one of those examples where snap polls are good for checking the pundit instinct, which is Vance was speaking pundit. This is an example of someone who, again, became famous as a pundit on the kind of outlets that you and I are used to, Why are you used to following?

Walls is different. His appeal is not quite speaking in those terms. In fact, it's about speaking to people who may value a different kind of approach, who want that more kind of plain spoken style, who might even be, you know, I wouldn't say suspicious, but not instantly enamored with someone just because they do a really strong performance for the, you know, Sunday show crowd. So the polls kind of were consistent with that, which is that they found that people really, really liked walls. They were split on who won, but they found that they liked walls

heading in and people's impression of him improved significantly from watching him, which is not something you would have necessarily gotten from the instant commentary, which is the traits that, you know, have made him likable did come through. But you saw the same thing with Vance, which was interesting, which is Vance, who, you know, was known for being unlikable heading into this, really improved his standing quite a bit as well. For him, that's a huge win. in any context, I'd say, just that even if you're not, you know, odds are low in a VP debate. You're going to change anyone's mind on how they're voting. It's really at the margins in that case historically.

But you can change people's impression of J.D. Vance a little bit. And I think the polling showed under the top line that more people seem to be like, oh, maybe I do like this guy. Maybe he's not who I thought heading in. So that was interesting. Below the top line, you also saw some encouraging things for Wall I would say. On the CBS poll, they showed on issues like the economy and inflation, similar to what we've been seeing in polling of swing states between Trump and Harris, they mostly fought to a draw. These are the big issues that the Trump campaign wants to talk about the most. And they did not

especially find Vance with some huge advantage on them. But they did find on the topics that Democrats want to talk about more, especially abortion, a big advantage for walls. So if you were trying to find encouragement there. You would say on they managed to fight, not do too much harm to them on the issues that are most harmful to them on the Democratic side and manage to score some points on the issues that they feel most confident about

and most want to have people talking about the next day and the day after and the day after. So I thought the polling was interesting, but it is kind of funny to have three separate polls find an exact perfect draw between the two candidates. It really gives everyone a lot to talk about.

Moderators were Nora O'Donnell and Margaret Brennan of CBS News. How did you think they did last night? I thought they did okay. As I said, I wasn't a fan of this first question, which is almost like a trick question. You know, it was like, will you invent some radical foreign policy position on the fly in a VP debate? But, you know, mostly things flowed pretty well. There was a lot of attention to fact-checking, and there was one fact-checking moment that I saw, once again, Republicans getting enraged over, and Democrats celebrating that I thought probably more was being made of than should have been.

And we could go over it a bit if you want to. But yeah. Yeah, they tried this fact check light approach where we're not going to, you know, contradict the candidate in real time. But when we get to the end of the section and the one you're referring to is about Haitian immigrants in Springfield, Ohio, when we get to the end of the section, we're just going to state the fact and then try to move on. But in this case, J.D. Vance didn't want to move. Yeah.

And it's not, and he didn't have, it's not. like he had no point either, which was they were just trying to clarify, not exactly fact-check him, they weren't exactly contradicting him, but just clarified that this discussion around Haitians in Ohio involves legal immigrants, which is true. This is primarily

about legal immigrants. Now, what J.D. Vance was trying to step in was make the case, make the case was well, look, a lot of the debate we're having about immigration is who should get legal status. That is the debate. You know, and arguing that Donald Trump would not be giving these people legal status. In fact, he tried to take it away

when he was president. And this gets into the policy weeds a little bit. Haitians are here mostly on temporary protected status, which is basically a kind of immigration status that says it is too dangerous for you to go back to your home country. And a lot of those Haitians didn't just, you know, come recently. You know, a large Haitian community has been here since 2010 after the earthquake there on temporary protected status. And since then you've had more come. There's been terrible political instability and violence there. That's one made it impossible to bring those people back,

but also encourage more people if they have the opportunity to come stay in America. So it's an interesting debate that a simple quick fact check doesn't quite capture, which is one of the problem of getting into the fact check weeds on this. And so I thought it was appropriate for them to clarify that. but I also thought it would have been fine to give J.D. Vance a minute to explain, hey, if you're going to fact check me, let me quickly explain my take on these facts and let Walls respond to. Because it was a very substantive disagreement that they were having there. The mods kept saying all night, we have a lot to get to.

They were even saying that an hour and 20 minutes into the debate when there were only 10 minutes left. We have a lot to get to. We must keep going. Please don't interrupt us. I think they cut the mics only one time. Do you think, Benji, this is the last debate at 2024? for? Probably. Some Democrats were trying to come up with this bank shot thesis that because Vance did so

well, Trump will feel that he was upstaged and have to prove himself again and demand another debate with Harris, which is you know, could happen. It's not like the, it's not the craziest read of Trump psychology I've ever seen. He's watching people like, you know, talking about how great Vance was on the cable shows he watches the next day, especially when they're talking about it in relation to Trump's awful performance in the first debate. So you never know.

Maybe that gets them off there. But on the other hand, if you're on the Republican side looking from a strategy standpoint, if you've decided that Trump is just not going to help himself into a debate, especially one right before the election, where it'll create a whole new can of worms inevitably that'll take up some of the last few days where people are voting, then you could also tell yourself and tell your candidate, well, we should just end here. We had a strong performance. You know, why we're feeling confident about where we are.

and let's just cut it off there, you know, and on a high note. So I think that argument might carry the day as well. I mean, the interesting thing in general, and I think this is one reason the debate was so friendly, both of these candidates were acting like they are part of a campaign that has a small lead and will win if they just don't make any obvious mistakes. And I think that's accurate. I think both of them kind of feel that way to some degree. They are not acting with the urgency of, oh, man, I am five points behind.

in every state, we have to just like frantically find some way to go get a hit in on the other candidate that just completely undoes their whole candidacy. They weren't going for wild home run swings on anything. And I think that may also cut against there being another debate. If things just sort of stay where they are in the polls and both sides can kind of talk themselves into the idea that, you know, the polls are basically tied, but we think we'll have the advantage on election day because either our ground game will be better or undecideds will all break to us at the last minute and we'll just narrowly win. If you both feel that way,

then I think there's less urgency to have another debate on either side. Finally, a lot of our friends on media Twitter last night were saying, hey, you know, vice presidential debates, they don't matter. And they were saying this while they were watching the vice presidential debate and analyzing it on Twitter. I always enjoy that little bank shot there. How much do you think this matters? Extremely little overall for the most part. I don't think it matters a lot. to the presidential condes. And indeed, in one of the snap polls, I think they had 1% of people on either side said they

changed their mind on who they're voting for, which is like you're getting into, you can get 1% to say anything. It could effectively be zero. It's pretty unusual for these debates to linger more than a day or two afterwards as well, you know, where people still are talking about them and they still have implications. And I think that's probably mostly going to be the case here. We'll get just another day or day or two. and then there's a lot going on in the news.

We'll be on to something else. But I do think it's very important for J.D. Vance's future, which was J.D. Vance, when he was picked, one of the reasons he was such a significant choice is that you were essentially minting him as the likeliest next nominee. Donald Trump was basically picking his successor, and because Donald Trump, if he wins, can only serve four years,

that's a really important pick. It means he's going to be effectively running for president immediately, as soon as Donald Trump takes office if he wins. But Vance was doing so poorly and was so unpopular, so quickly, that it wasn't looking quite so obvious that if, especially if Trump lost, Vance would have a political future that could get him on a presidential ticket again. This may have saved him in that regard, where he has some, a vision where Republicans can see, oh, after Trump, I see this guy has real assets.

We should definitely take a look at this guy. He has at least one signature moment now where he can point to for partisans being like, did you see how I took on, you know, Harrison Walls over there? Do you all remember how that made you feel? I can do that again. That could have big implications for his future. So I think that might be the more important aspect. Benji Sarland, you can read him at Semaphore.

You can see him sitting courtside at Nix Games. We're going to send up another bad signal soon. Thank you for coming on the press. Thank you, Brian. For years, I have read Gabriel Sherman's stories in the pages of Van Gogh. Fair and New York, and in the New York Observer before that. Now he is a screenwriter. The Apprentice, the movie he wrote about Donald Trump and Roy Cohn, opens October 11th. It stars Jeremy Strong and Sebastian Stan. I've seen it. I really enjoyed it. Right from the opening seat in which

Trump strides down the streets of burned out 70s, New York in a suit. Gabe, welcome to the press box. Thanks, Brian. It's good to be here. So I know your book about Roger A.L. was made into a series. How'd you come to write a screenplay about Trump? Well, they're sort of related. I covered Trump's 2016 presidential campaign for New York magazine. And in fact, I've been writing about Trump on and off for almost 20 years. My first job, as you mentioned in the opening, was at the New York Observer, where for a while I wrote the real estate column. And I was, you know, just out of college. And anytime I needed a quote, I could call up Trump's office and he would get on the phone and, you know, happily give a

quote. So, you know, it was such a shock to me that this tabloid blowhard was suddenly running for president. Anyways, when Trump won the election, had really something stuck with me that people who had known Trump since the 80s had told me that he was using a lot of the lessons that Roy Cohn had taught him. And I, at the time, time was adapting my Roger Ailes biography into a limited series at Showtime. So I had sort of started working somewhat in Hollywood. And thinking about this Roy Cohn connection, it just came to me in a flash. I was like, that's the movie. I was like, Trump is Roy Cohn's apprentice. And that's really was the kernel of the idea that I started to then develop the movie. For those who may be

a little fuzzy on Trump's origin story in the 70s, who was Roy Cohn? own. So Roy Cohn is this kind of larger-than-life figure whose shadow looms over, you know, the second half of the 20th century, and I would argue even today. He was a wonderkind young lawyer graduated Columbia Law School at, you know, something like 19. And he famously was on the map because he prosecuted the Ethel and Julius Rosenberg atomic bomb spy case. And then, that catapulted him to national attention. So then he went to Washington and fell in with Senator Joseph McCarthy, who was leading the congressional witch hunt for communist in government. Roy Cohn was his young assistant lawyer in the McCarthy Army hearings, was on-camera

interrogating government employees about their liberal and left-wing leanings. And, you know, really, When McCarthy's career ended in disgrace as, you know, kind of a vilified demagogue, Roy Cohn kind of went down the dent down with him. But then, you know, Roy moved back to his hometown of New York and in the 1960s reinvented himself as a fixer for the powerful and elite of the city. And he became the hired gun lawyer for society, people, business, CEOs, even mobsters. And so when Donald Trump met Roy Cohn in 1973, he was the most connected and influential behind the scenes fixer in the city.

We see them in an early scene in the movie meeting each other across a club. Cone sort of eyeing Trump and sending one of his minions over to fetch Trump and bring him to him. What does Roy Cone wind up doing for Donald Trump? Well, you know, that scene is, it's really interesting because, you know, we can maybe get into this later. But, you know, I also wanted the movie to explore so many layers to Donald and Roy's relationship. And one of them is the fact that Roy was closeted and, you know, throughout his life was gay, but insisted he was straight. But he had a coterie of young,

blonde boyfriends who, in my research, I was struck by how all these young men had this uncanny resemblance to Trump. And so in this first sense, scene. What's so interesting is that when he sends his lover and assistant over to invite Donald to dinner, it's kind of like really emotionally charged because you don't know is Roy hitting on him? What's his intentions? And it's only when Donald reveals his ambition to rise up through the world of real estate that Roy realizes that, you know, if there's not a romantic connection. There's really, you know, he can have influence and business influence over this young real estate heir. So the first thing that Roy did for Trump was that he defended the Trump

family in a federal housing discrimination lawsuit that the Justice Department had filed against Donald Trump's father, Fred Trump. The government in the early 70s accused the Trump family of discriminating against African American tenants and excluding them for the government. from their middle class housing developments in Brooklyn and Queens. And so Roy Cohn comes on the scene and says, screw this, don't settle with the government. File your own lawsuit. Go on the attack and make the government on the defensive

and make them prove their case. And that was really the genesis of their mentor-protech relationship. So funny, when Trump becomes president and his attorney general, Jeff Sessions, displeases him, he's quoted as saying, where's my Roy Cohn, aka, Where is the guy who will do what I want him to do and not ask too many questions about the ethical concerns that may be behind that? I know. I've seen throughout Trump's travails all of his legal entanglements and indictments.

You know, I sense, you know, it's obviously unspoken, but I just, I watch him and I imagine that there's part of him that just wishes Roy was still alive to get him out of this mess. Cohn, who is played by Jeremy Strong, gave Trump three rules of winning. Cones, if you will. Can you tell us what the three rules of winning are? Yeah, and we see them every day on the campaign trail. The first is always attack. The second is admit nothing, deny everything. And the third is always claim victory.

And so these three rules really define Donald Trump's entire political philosophy and strategy. And that's why I think the movie hopefully is so illuminating to viewers because it sort of reframes everything we're seeing today is actually not new. It's just repackaged

from what Roy had taught him 40 years ago. In the movie, Cohn also tells Trump a phrase that sports fans will be familiar with, play the man, not the ball. What did Cohn mean by that? It meant that, you know, there is no

There's no rules. There's no sort of ethical lines. You find whatever leverage you can and you exploit it. You know, Cohn famously used blackmail as leverage. He tape recorded his phone conversations. He, you know, used threats of outing people's private indiscretions to get them to do things. And so in Cohn's philosophy, you find whatever. weakness your opponent has and you play that. You don't actually follow the rules or try to find the best legal argument. So I think Trump obviously has also adopted that, you know, throughout his, his rise in politics. So for Trump, Cohn was a lawyer, a mentor, a fixer. What did Cohn get out of mentoring Trump? Yeah, that's, I touched on this earlier and I'll

circle back to it. But I think, you know, I think there, in some ways, I wrote the movie, as a love story. It is, you know, it's unrequited, but I think there really was this, Roy had this love for Donald that maybe started as sexual, but developed more almost into a father-son dynamic. So I think he got out of Donald this immense sense of pride, but also, I think, a legacy. You know, Roy obviously never marrying and not having children of his own, you know, wanted to have a legacy. that outlived him. And he found in Trump, someone who was so eager to to follow his rules that he knew that Donald would continue the Cohn philosophy into the future.

You mentioned Cohn existed in the 70s and kind of a state of semi-discrace from his work with McCarthy. Does Donald Trump and the work he did with Trump help him back fully into mainstream New York society? I don't think so. I think really by the this time, by this early, you know, they meet in 1973, Roy had really kind of shaken off the McCarthy baggage. You know, he was clearly an infamous figure. He was notorious and he kind of relished this kind of lawless out, this lawless reputation he had developed. But, you know, he had, you know, at the time, you know, many of the most powerful people in New York as clients, people like Cy Newhouse who owned the media empire, including Conday Nast.

He represented George Steinbrenner, who owned the New York Yankees. Andy Warhol was a client. The owners of Studio 54, Ian Schrager and Steve Rubell, were clients. So Roy had already kind of reintegrated himself into the New York Power Matrix. So Donald really didn't give him any. sort of, he didn't sort of wash his reputation. I think what actually Trump got a lot more out of the relationship because Roy facilitated so many of these, these powerful relationships that Trump would use for the rest of his life. You probably read this piece, but I read the story that Ron Rosenbaum,

who's a great journalist and also a former observer guy, did on Cohn, where they went to lunch. And Roy Cohn would eat at these fabulous New York restaurants, and all he would order for lunch was tuna fish. And Luserk. kept tuna fish and Hellman's mayonnaise in the back, just so they'd be Betty when Roy Cone walked in. Roy had the most bizarre eating habits. I mean, these were the kind of human textual details when I was researching before I was writing the script

that I just, I couldn't wait for an actor to dive into because, I mean, the truth is so much stranger than fiction. You know, Roy famously, his other technique was that he, his other habit was that he oftentimes would go to lunch at these very fancy Manhattan places and never order anything. And he would pick off of his dining partner's plates. He would just sit there grabbing food, taking an asparagus spear. And there's this really funny scene. It's actually not in the final cut of the movie, but we shot it where Donald and Roy go to lunch. And Roy keeps taking French fries and asparagus off Donald's plate. And at some point, Donald's

like, don't you want to order your own dish? And Roy, who's played by Jeremy Strong, says, no, no, I'm not hungry. But then he continues to just eat. It's just very, it's very eccentric. You know, his breakfast diet was every morning he would eat strips of bacon and slabs of cream cheese. This was before the Atkins diet had been popularized. So he would eat this pure protein breakfast.

He would put sweeten low into his champagne. God knows why one would do that. but there's the scene, actually the first scene in the film when Trump meets Roy at LaClaude. He's sitting at the table and he's watching Roy shake a packet of Sweet and Loat into the champagne flute. And you just see Sebastian does this kind of great moment where he's like grimacing of like, this is totally disgusting. So I found Roy's eating, bizarre eating habits to be kind of a manifestation of this character who was so outside the norm. of human behavior.

And so that's definitely a running line through the film. All right. So you've got this character on paper. How do you and the other filmmakers convince Jeremy Strong to play Cohn? You know, that's a great question. You know, Jeremy actually had been exploring a Roy Cohn movie independent of this, like years ago, a long time, you know, long ago, the project I don't think ever came. together. So I think Roy was definitely a character that Jeremy had been interested in.

And, you know, this was after, obviously, Succession ended. I think Jeremy's been looking to do, you know, all kinds of roles outside of television. And this, what I love about this, this role, and I really learned how talented Jeremy is as an actor is because, you know, He plays this character who's like the embodiment of cynicism and venality. And then the minute we wrapped shooting in January, he went right into rehearsals to play the lead in the Ibsen play, The Enemy of the People, which is the most idealistic kind of altruistic character. It's just you could not find a character that's more, that's different. And so I just, his range just shocked me.

Like, you know, going from like Kendall Roy on succession to Roy Cohn to this, you know, kind of heroic doctor who's trying to warn the village in this play about the evils of environmental pollution. It's just like he has his process. I don't know how he does it, but he becomes these different characters. His physicality in this movie is so amazing. Owen Glyberman. We cast him just from scheduling the way this movie was put together. I mean, he only really signed on to do the film like a few months before we started shooting. And he lost like 20 to 30 pounds in that time.

And he's not a big guy, obviously, to begin with. But yeah, the way he just threw himself into this character. And, you know, there's a scene in the film when he's doing another. one of Roy's strange habits was he would do 200 sit-ups a day. And so Jeremy was like, you know, doing these sit-ups and there's just like, he's just skin and bones. There's like nothing left to him. And I just was like, I was blown away by his commitment to doing the part. Owen Glyberman and Variety had a good observation that he would tilt his head. This is Jeremy strong, tilt his head down and then tilt his eyes up, which just gives him a very, very unique and

very sort of haunting look. I'm saying the movie is, in some respects, is a horror movie. It's kind of a, it starts out sort of fun, and you see you on this roller coaster ride with these two characters. And then it becomes something very different and very unsettling. And I think when I wrote the movie, and I think Ali Abbasier, director really delivered on this, I wanted audiences to leave the movie feeling like they have a pit in their stomach that we're now living inside this reality that Donald and Roy created. So, but anyways, back to your question.

Playing Donald Trump is so fraught because he's such a giant presence in our daily lives. So how did you and the other filmmakers come to Sebastian Stan? He was actually, you know, unlike Jeremy, Sebastian signed on very early, you know, Sebastian has been talking about this project with us since 2019. shortly after Ali came on to direct the movie. We've been trying to finance and get this movie made for years. And Sebastian was really one of the only, basically the only major Hollywood actor who kind of fearlessly said like, fuck yeah, I'm going to do this. You know, we went out to other actors who, for a variety of reasons, just didn't want to do the part.

I thought, you know, they didn't want to play Trump who they maybe disagreed with politically so much, or I don't, maybe they worried it would be too much like an S&L parody. But Sebastian was like, you know, from the beginning, he was like, all right, let's do this. And finally, when the money came together, you know, this was almost four years later, he still was interested. So I'll be forever grateful to Sebastian for having the guts to do this part because, you know, so many other people turned it down. How did you find the experience of writing a screenplay different than writing a magazine piece? It's very different, and it's even more different than television, writing television. You know, someone once told me that screenwriting is kind of anti-writing.

It's the words and the prose, it's, I mean, it matters to some degree, but every single word and line in the script has to either advance. plot or character. And so there is just no room for anything that's not sort of maniacally on point to the movie or the story you're telling. You know, magazine stories can have, you know, sort of go off in different veins. And there's there's, there's, there's just room to explore, you know, related ideas. and screenwriting is just because, you know, movie making is so expensive.

It's like you have to just be ruthless of just, you know, even if you really love something and if it's not advancing story or character, just, you know, have to just constantly be cutting it. So I think that kind of learning that discipline was something that took me some time to get used to. You know, because a feature film screenplay is only 120. 20 odd pages, and it's mostly white space. I mean, if you look at a, if you look at a script, it's, you know, some words in the middle and white space all around. So it's, it's just having, it's, I guess it's being economical is what I'm trying to say. You have to be just so efficient in what you're trying to say. I was watching the movie struck me that one challenge for you as a

screenwriter here is that Trump has no interior life, or at least admits to having no interior life. How did you deal with that as a writer? I think, well, first of all, I think what Sebastian did with the character is, kind of represents this, which is that when we meet Donald, he's kind of a blank slate. He's very different than the person we see today. He's soft-spoken. He's kind of unsure of himself. He's under the sum of his oppressive father. And basically, he's molded like a piece of clay.

by Roy into sort of becoming the caricature that we see today, the persona that we see today. So by the end of the film, you know, while it's still the 1980s, Donald is his mannerisms and his pattern of speech is very much similar to what we know today. And so basically my idea for the character is that it's just this slow kind of descent into somebody who's kind of loses their humanity for the sake of gaining power. And it's not, there's really no, no inner conflict. We sort of see moments where Donald maybe feels a little bit of conflict. And I guess I hope you introduce the segment, at least with spoiler alerts,

because I'm giving a lot away here. But, you know, the death of his older brother, Freddie, which Donald was somewhat responsible for, indirectly. So he feels a moment of guilt, but then just shuts it down. And so, like, I think that was my way of trying to dramatize somebody who, you know, is just a shell of a person doesn't really have an inner

conscience. There's a disclaimer at the beginning of the Apprentice that says this is based on real events, but of course like any film about real history, part of it is fictionalized. How accurate did you want this movie to be? I wanted the movie to be very accurate. You know, I think that was the lawyers, you know, put that there. So that's just, you know, that was a production consideration. But like the movie is, you know, is incredibly accurate.

You know, before production, I submitted an annotated copy of the script to the lawyers that was, you know, looked like a magazine article, fact checking with like every, every scene was annotated with where I sort. and how I learned that. And so the movie is rigorously researched. You know, that said, it's not a documentary. It's not journalism. It's drama. So, you know, I, the scenes, especially like between Donald and Roy is, you know, is my imagining of what those conversations were like.

You know, we have no, there's no record of those conversations. So that's obviously dramatized. And obviously, I had to take some license with timeline. compressing events to make it, you know, to tell one cohesive story in this 13-year time period. But in terms of like the actual major plot points of the film, everything that's in the film has, you know, there is a historical record that it happened. And so, so the movie is very much grounded in reality. But it's not, I just, yeah, it's not journalism. It's my interpretation of who I thought, this character of young Trump was.

Let me ask you about two scenes that stuck out to me and once again, spoiler alert. You mentioned Cohn helping Donald Trump beat that discrimination suit. In the movie, we see him showing a federal official some compromising photos of him and saying you would be wise to drop this right away. Where does that come from? That is, so that's an example of, you know, Roy has a documented history of using blackmail and sexual blackmail. But, you know, I found no obviously evidence that he did that specifically in that case for Donald. So that's, you know, again, my dramatization of Roy knowing who he was.

And, you know, people in New York were so shocked that the government settled without making the Trump's pay a fine or admit any wrongdoing. So that's an example where, you know, I'm, as a screenwriter, imagining, you know, this is how Roy could have shaped the case to be favorable to Donald. But yeah, that's an example of something that was dramatized based on who I knew Roy Cohn was. But, you know, there's not a specific example of that that happened as in the film. There's another scene in which Trump has depicted forcing himself on his first wife, Ivana. Where does that come from and why include it in the movie? That comes from Ivana herself.

So I'll get to where it comes from and then why, you know, I felt passionately it had to stay in the movie. So Ivana in her 1990 divorce deposition said under oath that Donald had, you know, violently assaulted her in their apartment. And, you know, in subsequent years, she, you know, changed her story in 1993 under pressure from Trump's lawyers. She said, she wanted to clarify that it wasn't a criminal act. And then when he was running for president, 25 years later, she said, oh, well, it's all nonsense. Like, you know, waters under the bridge. And so, you know, I felt Donald Trump's misogyny and alleged violence towards women, which he's been credibly accused of sexual assault by, you know, at least a dozen women.

A New York jury found him liable for committing assault against. the writer E. Jean Carroll. So this is a well-documented pattern of behavior, which obviously Trump denies. I felt as the writer that it was important that this aspect of Trump's character be explored in the movie. It's not his entire character, but obviously as we're trying to show the evolution of Trump into the man we all live with today, this aspect was as important. and Ivana made this allegation in real time under the threat of perjury. So when I looked at her other statements, they didn't hold up to me. Donald's lawyers made her issue a clarification before our book came out.

Like, you know, perhaps she was just trying to protect her divorce settlement. And then later when he was running for president, you know, she's the mother of his children. their father has a chance to be, you know, in the Oval Office. Like, I just felt that the thing she said closest to the alleged event with the highest threat of lying felt the most emotionally true to me. That felt true. And so, as a dramatist, that felt like the right thing to put in the movie. All right. Two quick ones for you, Gabe, before you go.

When you watch Trump campaign for president for the third time, where do you see? and where do you hear the legacy of Roy Cohn? I mean, I hear it every day. There's a fan. Somebody posted on Twitter a clip of Jeremy Strong saying Roy Cone's rules. So it's lines from the movie from the trailer, juxtaposed with Kamala Harris and Trump debating her on ABC last month. And it's like it's just uncanny where.

you hear, you know, Roy saying, attack, attack, attack, and then you hear Donald Trump calling Kamala Harris a Marxist. Then you hear him like, you know, admit nothing, deny everything. And, you know, he's denying he ever touched classified documents. And then there's the line where you say, always claim victory. And then, you know, Trump's, you know, blathering about how he won the 2020 election and it was outrigged. And, you know, so you hear all of his major political attack lines are influenced by Roy Cohn's three lessons. And so I just think it's inescapable that we, that Donald Trump would get, would have gotten to where he is if it wasn't for Roy Cone's influence. What do you do now? You go write more screenplays? You go write more

journalism? Well, I, I, I'm a correspondent for Vanity Fair. So I'm actually, I'm covering the Trump campaign, Trump campaign and still doing, you know, journalism. And, you know, I love screenwriting, but I also love journalism. I think they're complementary. They're obviously very different mediums. I find the pace of Hollywood can be very frustrating. You know, it takes years. There's so much heartbreak in show business of, you know, you get committed to a project

and you pour your heart into an idea and then, you know, it just doesn't happen or it falls apart. And so I find the immediacy of journalism to be. be very refreshing. I think I'd go crazy if I was, wasn't writing regularly, um, and reporting news because then I would just be kind of a way in my, in my office, just writing scripts that, you know, will take years before the world sees. So, um, you know, that's gets a long answer of saying, I'd like to, I'd like to continue doing both. Um, and, um, we'll see, hopefully that will happen. The world is going to see the Apprentice on October 11th, Gabriel Sherman, thank you for coming on the press box.

Thanks, Brian. Take care. That is the press box. I'm Brian Curtis. Bracks and Magic by Brian Waters. Since we're having full disclosure month here at the press box, I want to note that Briarcliff, which is releasing the apprentice, is also releasing, and this is a very, very deep cut for press box listeners. The movie, When I'm Ready, where I have a very small part as a radio DJ. Now, let me assure you that I am not at Hollywood Star, so I gain nothing from this association. But full disclosure. All right, guess what? We are not done with the press box this week,

because tomorrow, Thursday, Beaumani Jones is going to be on the podcast. Beaumani Jones. Cannot wait to talk to him. And I'm already filling out the October schedule. Thursday, October 10th, Eugene Daniels, one of the authors of Politico's playbook. is going to be on this show. Lots and lots to discuss as we get closer to the election. I will talk to you tomorrow with more lukewarm takes about the media. See you then.