Hollywood executives love to characterize themselves as fearless. The truth is that they spend most of their time trying to minimize risk.
It’s why theaters are clogged with vacuous sequels. It’s why so many Hollywood power players hide behind P.R. people. And it’s why all of the big movie studios and streaming services — and, in fact, most indie film companies — declined to distribute “The Apprentice,” a dramatized origin story about Donald J. Trump that the former president has called “malicious defamation” and showered with cease-and-desist letters.
But the movie business still has at least one wildcatter: Tom Ortenberg.
Mr. Ortenberg, 63, and his Briarcliff Entertainment are pushing to complete a deal to acquire “The Apprentice” for wide release in theaters in the United States in September or early October — close enough to the presidential election to bask in its heat, but far enough away to avoid final-stretch media overload. Briarcliff’s pursuit of the $16 million film was confirmed by five people involved with the sale process, who spoke on the condition of anonymity to discuss a private negotiation.
“Tom’s got more courage than most people in Hollywood combined,” said Stephen Galloway, the dean of Chapman University’s film school. “His interest in this kind of movie involves business, of course. He sees money to be made by leveraging millions of dollars in free publicity. But part of it is wanting to do his bit. He’s liberal and cares about social issues.”
Hurdles remain, the people cautioned. “Apprentice” producers cobbled together the money to make the movie from various sources. One was Kinematics, an upstart film company backed by Dan Snyder, the former Washington Commanders owner — and a Trump supporter. Kinematics, which invested about $5 million, would need to sign off on the Briarcliff deal and has balked, calling the offer subpar, according to the five people involved in the sale process. The Kinematics snag was reported earlier by a Puck newsletter.
So producers have put together a package to buy out Kinematics at a premium. The sides are now haggling over terms, including the timing of payment.
Briarcliff will need to move quickly to engineer a fall release: Marketing materials must be prepared; theaters must be booked (and some might refuse). “The Apprentice” has reached distribution deals for Canada, Europe and parts of Asia. Once theaters overseas begin playing the film (sometime this fall), it will become available on global pirating sites, reducing its value to a U.S. distributor.
Mr. Ortenberg declined to comment. A spokeswoman for the film and its lead producers also declined to comment, as did Kinematics.
Over his four-decade movie career, Mr. Ortenberg has repeatedly championed movies deemed too hot to handle by the Hollywood establishment. Not all of his bets have paid off. But some have — spectacularly.
In 2004, after Disney refused to release “Fahrenheit 9/11,” Michael Moore’s flame-throwing documentary about the George W. Bush administration and the 2001 terrorist attacks on the United States, it was Mr. Ortenberg, then president of a fledgling Lionsgate, who picked up the film. When theaters in conservative pockets of the country refused to play it, Mr. Ortenberg went on the attack.
“What these chains are doing is a horrible precedent for the movie business, and it shows exactly how fragile the First Amendment is,” Mr. Ortenberg told The New York Times at the time. “Fahrenheit 9/11,” which counted Harvey Weinstein as a producer, collected $222 million in global ticket sales, or about $368 million in today’s dollars, the most ever for a documentary. The documentary cost less than $10 million to make.
Mr. Ortenberg’s résumé also includes Kevin Smith’s “Dogma,” a profane 1999 religious satire that was greeted by protests, boycotts and death threats, and Oliver Stone’s “W,” a comedic 2008 skewering of Mr. Bush. Mr. Ortenberg was also behind “Spotlight,” the Oscar-winning newspaper drama from 2015 about the Roman Catholic Church’s cover-up of sexual abuse by priests.
In 2020, Briarcliff distributed “The Dissident,” about the murder of the Saudi journalist Jamal Khashoggi and attempted cover-up by the Saudi government. In that case, too, Mr. Ortenberg stepped in after Hollywood companies balked at distributing it. “The Dissident” was a flop in limited theatrical release, but found a modest audience on home video.
“The Apprentice” debuted to mostly favorable reviews at the Cannes Film Festival last month and dramatizes Mr. Trump’s origin story, focusing on his rise in New York real estate in the 1970s and ’80s and mentorship by Roy Cohn, the unscrupulous power broker. Sebastian Stan, known for his role as Bucky Barnes in Marvel superhero movies, plays Mr. Trump. Jeremy Strong portrays the pugnacious Cohn, complete with burnt-bacon tan. Mr. Strong, an Emmy winner for HBO’s “Succession,” recently won a Tony Award for his performance in “An Enemy of the People” on Broadway.
Briarcliff plans to position both actors as Oscar contenders, according to the people involved with the sale.
“The Apprentice” also stars Maria Bakalova (“Borat Subsequent Moviefilm”) as Ivana Trump. One incendiary scene shows Mr. Trump throwing her to the ground and assaulting her. In real life, she accused him of rape in a deposition related to their 1991 divorce. She later disavowed the claim, saying she did not mean rape in the “criminal sense.” She died in 2022.
Kinematics, citing potential legal liability, pushed the film’s director, Ali Abbasi, to remove or trim down the already brief scene before the Cannes premiere; Mr. Abbasi refused. Other scenes in the film depict Mr. Trump as hooked on speedlike diet pills and having fat surgically suctioned.
Last month, Mr. Trump threatened to sue to block the film’s release. “This garbage is pure fiction which sensationalizes lies that have long been debunked,” Steven Cheung, a spokesman for the Trump campaign, told reporters at the time.
A lawsuit from Mr. Trump would cause headaches for Briarcliff and the producers, but courts — citing First Amendment protections — have consistently sided with filmmakers in similar cases over the years.
The lead producers of “The Apprentice” are Amy Baer, the founding chief executive of CBS Films and a former Sony Pictures executive, and Daniel Bekerman, a scrappy indie producer with credits like “The Witch” (2015). “The Apprentice” was written by Gabriel Sherman, who is known for “The Loudest Voice in the Room,” a best-selling 2014 biography of Roger Ailes, the disgraced political operative and Fox News leader.
Companies that passed on “The Apprentice” declined to comment or did not respond to queries. They included Focus Features, Sony, Searchlight, Netflix, Metro-Goldwyn-Mayer, Amazon’s Prime Video and A24.
In conversations with sales agents for the film, the uninterested companies justified their stance with various explanations, according to the people involved with distribution negotiations for the movie. A couple of potential distributors thought the film was good but not good enough to risk the almost guaranteed blowback — not just from Mr. Trump’s lawyers but from the broader MAGA world.
Other potential distributors worried about regulatory retribution from Mr. Trump should he be re-elected. During his first term, Mr. Trump’s Justice Department tried to block AT&T’s acquisition of Time Warner, which owned CNN. The move was widely seen as retaliation for CNN coverage that angered Mr. Trump.
The box office prospects for “The Apprentice” are unclear. Sequels have been succeeding, but original movies — dramas especially — have been struggling to break through. Politically minded films have largely moved to streaming. “The Apprentice” could also fall in a chasm, with Trump supporters boycotting and liberal audiences repulsed.
“I have a hard time seeing any red-collared American going to see it,” said Mr. Galloway of Chapman University. “Will others want to pay 20 bucks to consume even more Trump? Maybe. Maybe not.”