Jack Bryan was your average Upper East Side-raised son of a millionaire trying to get his filmmaking career started when Donald Trump began persistently popping up in his life. In New York Citys social circuit, Bryans father, Shelby Bryan—a telecom mogul and Democratic donor—was friendly enough with Trump, perhaps because both are relative outsiders (Bryan being from Texas, and Trump being Trump). On vacation in Palm Beach in 2008, the Bryan family was immersed in the scuttlebutt about how a then financially strapped Trump had curiously managed to sell a Palm Beach estate hed bought for $41 million to Russian oligarch Dmitry Rybolovlev for $95 million. Around 2012, Shelby Bryan shared a car to the U.S. Open with the real-estate tycoon, after which he told his son, “That guy sure does like Russia.” The elder Bryan (who is also the longtime partner of Condé Nasts artistic director, Anna Wintour) also brought his sons, Jack and Austin, on a golfing trip to the United Kingdom, where Trump gave them early access to his Trump International Golf Links course in Scotland and chatted with them after their game.
To Jack, Trump registered as a “harmless clown who would appear in the tabloids.” But as Trumps political ambitions solidified, the younger Bryan began to take notice. A self-described “pragmatic lefty,” he had often texted with his friend and fellow politics junkie Marley Clements about world affairs. When Clements proposed that Russians may have been involved in the hacking of the Democratic National Committee during the summer of 2016, Bryan expressed skeptical interest.
Then, in March 2017, former F.B.I. agent Clint Watts testified to the Senate Intelligence Committee that Trump himself had engaged in “active measures”—a term that describes the Russian propaganda tactic of using disinformation and manipulation of events to promote its foreign policy. Thats when Bryan said to Clements, “Somebody needs to make a film about this.”
Active Measures, a dizzying and rigorously researched documentary, premieres at Torontos Hot Docs film festival this week, where C.A.A. is representing the film in its hunt for a distributor. It is 33-year-old Jack Bryans effort to connect the dots between Trump and Russia, including Vladimir Putin himself. “I want to alert people, and I knew no one else was going to do it in time for the midterm elections,” he said over beers at Williamsburgs Radegast Hall recently. “I felt like I could.”
The story of Jack Bryan smacks like fiction. Hes an oddball rich kid, the vulnerable, good-looking scion of a well-connected Manhattan family, who got thrust into radically different circumstances when he used the powers at his disposal—filmmaking and access to friends-and-family financing—to realize the solemn words his father once said to him: “You are going to have advantages, and that means two things: you wont have any excuses, and you will also have a responsibility to be of service.”
Bryan wrote his first film when he was 16—a fictional piece involving a kidnapping—and took classes at the New York Film Academy. His schooling included stops at Buckley School (Donald J. Trump is an alum) and the Kent boarding school in Connecticut, from which he dropped out before attending rehab (he said he had depression issues). He finished high school at Montana Academy, a self-described “therapeutic school.” After arriving home to New York to study media and film at the New School at the age of 23, Bryan made a documentary about the seedy, beloved Siberia Bar, landed a job at a production company, and directed two micro-budget indie dramas, one of which had a minor theatrical release in 2015. (The New York Times called it a “ mere genre exercise.”)
He was in pre-production on another small narrative film, this one a 24-hours-in-New-York-wild-ride drama, when he decided to pivot to Active Measures. The filmmaker moved to a friends house in Maryland—he called it “the bunker”—where he and Clements spent several weeks studying the evidence, scrawling their ideas on window glass and large sections of cardboard to help envision the web they were trying to connect. Also on the team was Laura DuBois, Bryans girlfriend and an experienced producer, whom Bryan calls “the boss of the movie.”
Bryan said that the thesis and main points of Active Measures havent changed much since they first sketched it out in the bunker—its just that their once apparently too-ludicrous-to-be-real collusion narrative has become more plausible. Audiences will see this in the films highlighted news clips and in-depth interviews with respected world leaders, think-tank wonks, former C.I.A. and State Department officials, academics, and Capitol Hill veterans, including Senator John McCain and former Democratic presidential nominee Hillary Clinton—who provides insight into Putins psyche, including a wry aside about the Russian leaders tendency to manspread.
After a second beer at Radegast, Bryan was off to his apartment to review post-production on the film. Eventually, more accomplished documentarians will have Trump stories to tell. (Michael Moore is currently wrangling a release for his own big Trump film, Fahrenheit 11/9, which is currently stalled because of the Weinstein Companys implosion.) But for now, Bryan is happy to be in front of the pack. “Until the cavalry comes, people need to know whats going on,” Bryan said, brushing away the hair falling on his forehead. “Until the pros show up, Im what youve got.”
Get Vanity Fairs HWD NewsletterSign up for essential industry and award news from Hollywood.Full ScreenPhotos:Vanessa Trumps Life as a Model and Socialite, in Photos