When the screenwriter and Vanity Fair correspondent Gabriel Sherman woke up on the morning of 14 October and looked at his phone, he realised he’d experienced a rite of passage for political reporters in New York and DC: Donald Trump had singled him out for an excoriating takedown on social media.
The night before, the former president had taken to his platform Truth Social to post: “A FAKE and CLASSLESS Movie written about me, called The Apprentice (Do they even have the right to use that name without approval?), will hopefully ‘bomb.’ It’s a cheap, defamatory, and politically disgusting hatchet job, put out right before the 2024 Presidential Election, to try and hurt the Greatest Political Movement in the History of our Country, ‘MAKE AMERICA GREAT AGAIN!’…. The writer of this pile of garbage, Gabe Sherman, [is] a lowlife and talentless hack.”
Sherman’s film, The Apprentice, is a biopic that follows the rise of Trump in the 1970s and 1980s, and his years-long friendship with the notorious New York lawyer and political fixer Roy Cohn, then best known for his work with Joseph McCarthy in rooting out communists in the US government. It was Cohn who taught a young Trump his three rules for success: Number one: attack, attack, attack. Next: deny everything. And lastly: always claim victory. When I met with Sherman in a central London hotel the morning of Trump’s post, he held up his phone, reading the diatribe aloud. “I don’t know if that means he is going to sue,” he said, shaking his head and laughing, “but I mean it is definitely an example of: attack, attack, attack.”
Sherman, who spent years covering politics and media as a journalist for publications such as New York Magazine and Vanity Fair, started writing the screenplay, his first feature film, months after Trump won the 2016 election. Back then it still seemed astonishing that “Trump was speaking in this very personal and vicious style that politicians didn’t talk like that. Everyone was like, ‘Where did this come from? This is unprecedented.’ Trump’s long-time adviser Roger Stone and others told me that Trump was just using the lessons and the strategies that his mentor Roy Cohn taught him,” he said. Sherman began researching the pair’s relationship, and found “a Frankenstein story of how Roy Cohn moulded Trump’s personality into the person he became”.
The Apprentice is a blistering portrayal of Trump (played by Sebastian Stan), who under the tutelage of Cohn (Succession’s Jeremy Strong), learns to manipulate – or just flat out ignore – the law in order to amass money and power. The transformation is ugly in many ways: Trump is depicted raping his first wife Ivana (an incident the real-life Ivana alleged took place in her divorce deposition; she later retracted her claim); getting liposuction after failing to lose weight on amphetamines; and betraying nearly everyone he knows. (Roger Stone and The Art of the Deal ghostwriter Tony Schwartz, who are both portrayed in The Apprentice, have praised the movie.) Trump also eventually turns on Cohn, a closeted gay man who died of Aids in 1986, but not before he’d fully absorbed the fixer’s rules for success.
In 2024, these Cohnian rules seem obvious hallmarks of Trump’s style– particularly rule number three, always claim victory. But Sherman had written his first draft of the screenplay long before Trump was claiming the 2020 election was stolen. “I couldn’t have predicted 2020, and January 6,” he told me. Watching news coverage of the Capitol attack, he thought, “Wow, this movie took on a new level of importance for me.”
With the next election just days away, what does Sherman think will happen? “I think we’re probably looking at the very real possibility that even if he loses, we’re going to have 2020 repeat,” he said. “He’s told us what he’ll do: he’ll claim victory… We should take Trump at his word: he does what he says he will do.”
At 45, Gabriel Sherman has spent more than 20 years covering Donald Trump. After graduating from the liberal arts college Middlebury in Vermont with a degree in political science, Sherman moved to New York and started working at the New York Observer under legendary editor Peter Kaplan. “I was assigned to cover the real estate column, which every week was chronicling the highest-profile sales in Manhattan, and trends in real estate. So I started interviewing Trump when I was in my early twenties,” he told me. “He’s been this figure that has been in my professional life for so long.”
At the time, Trump was far less hostile to journalists and incredibly easy to get on the phone; Sherman could always reach him for a comment. “Back then – this was before The Apprentice TV show – he was just known at the paper as a tabloid character, a kind of blowhard, a buffoon.” (Trump’s future son-in-law, Jared Kushner, would go on to purchase the NY Observer in 2006, when he was just 25; he sold his stake in the company to a family trust in 2017 so he could become an adviser in Trump’s administration.)
Sherman went on to work for New York Magazine, where he would cover two of the title’s most tumultuous beats: politics and the media. After years of reporting on Fox News, in 2014 he published The Loudest Voice in the Room: How the Brilliant, Bombastic Roger Ailes Built Fox News – and Divided a Country, an expose of the network’s predatory president. The book was critically praised, an immediate best-seller, and later turned into a television mini-series starring Russell Crowe as Ailes.
But covering Ailes was a first-hand lesson in the chilling way the powerful can crush opposition. The notoriously volatile Ailes hired investigators to surveil Sherman as he reported the book, eventually compiling a 400-page dossier of opposition research on the journalist in order to smear him. Ailes was forced to resign in 2016, after a wave of women working for Fox accused him of sexual harassment, which Sherman covered. When Politico reported a few months later that Ailes had threatened to hire people to “beat the shit out” of Sherman, New York Magazine provided him with a bodyguard.
Ailes died in 2017 at the age of 77, but not before he became an adviser to Donald Trump’s presidential campaign.
Though Sherman seemed to laugh off Trump’s “attack, attack, attack” strategy when it was turned on him, it’s true that his film did face an uphill battle to get made. When he first shopped his script around, Trump was still in office and “no producers in Hollywood wanted to touch it”. Then, “January 6 happened, and that freaked the world out. People were like, ‘is he the next Hitler?’”
Eventually Sherman found a coalition of producers willing to back the film and it debuted at the Cannes Film Festival earlier this year. The premiere was a critical success – it received an eight-minute standing ovation. But then Trump attacked. After the premiere, “Ali Abbasi, the film-maker, and I both received personal letters from Trump’s lawyers, a cease and desist, basically saying, ‘If you proceed with this movie, we will sue you,’” Sherman told me. The threat “had the effect of really chilling any interest, commercial interest in the movie, like all the studios and streamers, saw this legal threat and actually took it seriously.” The end result was that they left Cannes without any American studio offers to distribute the movie. “One person told me that no studio in Hollywood wants to – quote – ‘buy a lawsuit’.”
Yet Sherman later learned that it wasn’t just wariness over one potential lawsuit; studios didn’t want to make a powerful enemy. “These companies, big entertainment companies, worried that if they bought the film and Trump became president, he would then use the power of the government to punish their business – do an IRS audit of them or use the Justice Department to investigate them.”
Briarcliff Entertainment, an independent production company, eventually agreed to distribute the movie in the US. But it’s clear that Hollywood firms aren’t the only businesses grappling with the fear of a second Trump administration. When the Los Angeles Times and the Washington Post both announced in late October that they were abandoning precedent and opting not to endorse a candidate ahead of the 5 November election, perhaps due to their respective billionaire owners’ concerns over a potential Trump presidency, the backlash from journalists across the industry was swift. (Readers of both publications were also clearly dismayed as the announcements triggered a tsunami of cancelled subscriptions.) These concerns aren’t without merit: Trump has repeatedly threatened to destroy his so-called enemies if he returns to power. On 31 October, Trump filed a lawsuit against CBS News, claiming the network’s 60 Minutes interview with Kamala Harris was edited in a “deceitful” way, which “amounts to a brazen attempt to interfere in the 2024 US Presidential Election”.
Sherman describes that trend, of opting to self-censor to avoid retaliation from a tyrant, as “chilling”. Yet he also acknowledges the danger of Trump returning to the White House. “He’s become older and less sane and angrier,” he told me. “What I find troubling is that he now understands the limits of what a president can and can’t do. And if he wins again, he’s going to only want to surround himself with sycophants who will just do what he wants. I think there will be far fewer guardrails on him in a second term than there were in the first term.”
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