Liposuction, drugs, and blackmail: The true stories behind the biopic “The Apprentice”

"The funny thing is, everything in the movie that seems the most shocking is actually completely based on real events," screenwriter Gabriel Sherman tells EW.

Warning: This article contains spoilers for The Apprentice.

A good rule of thumb for those watching The Apprentice: If a scene seems too outrageous to be true, it probably is.

“The funny thing is, everything in the movie that seems the most shocking is actually completely based on real events,” the film’s screenwriter, journalist Gabriel Sherman, tells Entertainment Weekly. “Very little has been dramatized. It's one of these stories where the truth is stranger than fiction.”

Sherman wrote the controversial new film, which follows a young Donald Trump's rise to power under the mentorship of his notorious attorney, Roy Cohn, after covering the former president for the better part of 20 years, first as a real estate reporter at the New York Observer and later as a political reporter for New York Magazine.

While Sherman and the filmmakers intend to humanize Trump, the movie does not present an altogether flattering portrait of the future president. Throughout The Apprentice, the real estate mogul, played by Sebastian Stan, is seen taking diet pills, battling erectile dysfunction, getting plastic surgeries, and, in the film’s darkest moment, raping his wife Ivana, (Maria Bakalova) as she testified happened in her divorce deposition. (Ivana later denied her initial testimony, saying she felt "violated" but did not mean to allege rape "in a literal criminal sense.”)

Given the controversial material and their famously litigious subject, Sherman and the filmmakers were careful to thoroughly vet the script before the cameras rolled. “I submitted an annotated draft of the script to our lawyers that was point-by-point articulating where the information came from, and how I dramatized the scenes,” Sherman explains. “So it was rigorously supported by the research, and everyone on the filmmaking team was comfortable with that before we went into production.”

Below, the journalist elaborates on the backstory behind some of the movie’s most outrageous moments, revealing what was dramatized and what was ripped straight from the headlines.

Related: Will Donald Trump see The Apprentice? The cast and filmmakers weigh in

The blackmail tapes

Trump’s greatest early victory in real estate was the construction of Manhattan’s Grand Hyatt Hotel in 1978. He was able to complete the deal thanks to a substantial loan from his father, and an enormous $400 million tax abatement from New York City, which happened to be bankrupt at the time. In the film, Trump is only able to secure the tax break after Cohn (played by Jeremy Strong) blackmails a city official with a compromising phone call, which he had illegally recorded.

“Roy's use of blackmail, and especially tape recording phone calls, is well documented,” Sherman explains. “Roy had a woman in his basement who actually ran a switchboard, and she would tape and listen to all the conversations. I found it so powerful that Roy would basically tape-record his own clients for blackmail and for leverage. I thought that was a way to illustrate to Trump his philosophy for winning, and how you have to be willing to almost betray your own people to win."

Whether Cohn actually utilized blackmail tapes to help Trump secure a tax abatement for the Grand Hyatt is unknown, but it does seem that the lawyer’s dirty tricks were at play in the arrangement. “Stanley Friedman, the deputy mayor at the time, signed off on the deal at the last second, shortly before he left office, and then went to work for Roy Cohn at his law firm a week later. So basically, Roy gave a job to the city official who got the deal for Donald.”

Related: How Sebastian Stan transformed into Donald Trump for The Apprentice — with help from soy sauce and ramen

The parties

Cohn was known for throwing lavish parties at his Manhattan home, which also doubled as his law office. In the film, as his famous guests do drugs and strip off their clothes, an out-of-place, sober Trump seeks out Cohn for company and stumbles upon him having sex with a man.

“Roy's townhouse parties were famous because he mixed all of his different worlds together,” Sherman says. “Roy was really at the intersection of the underworld and the legitimate world, so you had his mob boss clients, but then you had Upper East Side society ladies, and these people like Rupert Murdoch, George Steinbrenner, and Andy Warhol. Roy basically opened the door and allowed Donald access to the secret world.”

Still, Cohn’s house parties were not usually fueled by drugs and sex — that would happen later at Studio 54. But since it was too expensive to recreate the famous disco on screen, the filmmakers decided to shoot the wild partying after hours at Cohn’s home.

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“Now, in terms of the after-party and the debauchery, that scene was actually made for production reasons in the script,” Sherman explains. “We had planned to shoot the after-party at Studio 54 because Roy represented [Steve Rubell and Ian Schrager,] the owners of Studio 54, and Roy was a frequent guest at Studio 54, which was, of course, famous for its complete excess and drug-fueled parties.”

While it’s unclear whether Trump ever walked in on Cohn having sex, it was no secret that the attorney was gay. “He wasn't shy about it,” Sherman says. “I felt like the movie needed to dramatize and really capture that aspect of Roy's sexuality and also make Donald wrestle with this unspoken truth that no one ever really talked about, but everybody knew. So I thought it would be really compelling to have Donald come face to face with Roy's sexuality, but they never spoke of it ever again.”

Related: The Apprentice filmmakers on 'shocking' struggle to find a buyer: 'It's cowardice in the face of Donald Trump'

The prenup

One of the film’s funniest scenes depicts Cohn meeting with Trump and his fiance, Ivana, to go over the prenup he’s crafted for them. Sitting together in a restaurant, Ivana reads through the paperwork carefully, much to Cohn’s chagrin. When she gets to a clause stipulating that she return any gifts in the event of a divorce, she storms away from the table and threatens to call off the wedding. Trump is only able to convince her to stay with him after chasing her into the street and professing his love.

"What I was struck by in the research was it really didn't take much to bring to life on the page because the real events were so dramatic to begin with. And that divorce scene is pretty much almost verbatim how it's been recounted in different books,” Sherman says. “The last straw was the gifts. She couldn't believe that Donald would make her return the gifts.”

Even Trump chasing Ivana into the street is based on real reporting. “The sidewalk scene was inspired by Harry Hurt's book, Lost Tycoon, which recounts how Donald ran onto the sidewalk and convinced her to come back into the restaurant.”

One small variation from the film is that, in real life, Ivana had a lawyer with her at the meeting. But, as Sherman explains, “It was a lawyer that Roy arranged to have for her. So the lawyer was basically in on it with Roy. It was so corrupt.”

Related: The Apprentice star Sebastian Stan explains why he thinks 'there's a Trump in all of us'

The plastic surgeries

At the end of the movie, Trump visits a plastic surgeon to address his receding hairline and expanding waistline. First, the doctor advises that Trump stop taking his weight loss medication, which he equates to cheap speed. When he then recommends diet and exercise, Trump informs him that the human body has a finite amount of energy that must not be wasted on physical exertion — an argument he’s continued to make over the years. So, he instead opts for liposuction and scalp reduction surgery.

While Trump has denied going under the knife in the past, the scene is once again based on actual reporting in Lost Tycoon. “In Ivana's divorce deposition, which she said under oath, she talked about how Donald got liposuction, scalp removal surgery, and was also taking diet pills. So that scene really was something that was backed by the record,” Sherman says.

As far as Trump's "ridiculous ideas" about exercise, "I thought that was a really appropriate place to show that he's not interested in actually working to get in shape," Sherman continues. "He just wants the quick fix of the surgery.”

Related: Made in America: How polarizing biopic The Apprentice charts Donald Trump's origin story

The rape scene

One of the film’s most controversial scenes depicts Trump raping his then-wife, Ivana (who died in July 2022), in their home. The assault occurs after Ivana, dissatisfied with their love life, gives Trump a subtle hint for his birthday, 1982’s international best-seller, The G Spot and Other Recent Discoveries About Human Sexuality. Already souring on their marriage, Trump doesn’t take the playful jab at his manhood well and attacks Ivana in retaliation.

While the assault is based on Ivana’s 1990 divorce deposition, the circumstances leading up to it are different in the movie. “Her deposition is actually much more graphic than what we depict in the film,” Sherman explains. “As she described it, Trump was recovering from his scalp surgery and was having these debilitating headaches, and she kind of provoked him, and he flew into a rage and threw her down on the bed and pulled out her hair and assaulted her.”

He adds, “The scene that we dramatize in the movie is a compilation of that scene, but also the fact that near the end of their marriage, Ivana talked to her friends about how their sex life had basically disappeared, and she bought this book and showed her friends over lunch. In a certain way, it's actually a more tragic scene because she's trying to connect with him. She's reaching out to him.”

Related: See all the photos from Entertainment Weekly's The Apprentice cover shoot

The cufflinks

After reconciling from a serious fallout caused by an unpaid hotel bill, Trump gives Cohn a pair of diamond cufflinks for his birthday. In one of the film’s most tragic moments, when Cohn proudly shows the gift to Ivana, she quietly reveals to the attorney that they’re knockoffs.

While it’s unlikely that Ivana delivered that news in real life, Trump really did give his former best friend and mentor a pair of phony cufflinks. However, the moment was not initially in the script. “That was Jeremy Strong's idea,” Sherman reveals. “Jeremy had done so much research into his character, and when we were doing script notes, he told me that great story that I'd remembered but hadn't included it in the script about how Donald gifted Roy these fake diamond Tiffany cufflinks.”

He adds, “It was just such a great idea that we put it in because it is just the perfect expression of Donald's shamelessness.”

The Apprentice is now in theaters.

Read the original article on Entertainment Weekly.