Mr. Stone’s high jinks did not prevent him from at one point becoming part of the Washington establishment. Alongside Paul Manafort, the former Trump campaign chairman convicted of financial fraud, he created the powerhouse consulting firm Black, Manafort and Stone in the 1980s. The firm, a product of Reagan-era Washington, helped create the “swamp” culture of selling influence, representing, among other clients, dictators and foreign political parties that were accused of ties to drug trafficking.
One of their early clients was Mr. Trump, who had been introduced to Mr. Stone by Roy Cohn, Mr. Trump’s longtime lawyer and mentor, who also counted Mr. Stone as one of his protégés.
Their relationship, over the years, has proved to be fraught but durable, marked by repeated falling-outs and reconciliations. In 2011, Mr. Stone was involved in Mr. Trump’s deliberations over running against President Barack Obama. He gave interviews saying that Mr. Trump had billions to spend on a campaign, and laid out a message that was close to Mr. Trump’s “Make America Great Again” slogan of 2016. But when Mr. Stone got too much attention, Mr. Trump told reporters that his adviser was not speaking for him.
Mr. Trump eventually opted out of a race in 2012, choosing instead to continue on with his reality show, “The Apprentice.” When Mr. Trump briefly explored a potential run for governor in New York in 2013, Mr. Stone advised against it. Mr. Stone was one of the few early aides involved in the 2015 race until he quit a few months into the campaign; Mr. Trump insisted Mr. Stone was fired.
Since taking office, Mr. Trump has at times become enraged at what he sees as excessive news media attention surrounding Mr. Stone. People close to the president have long maintained that he is leery of his old adviser, only interested in keeping Mr. Stone near enough that he would not feel cast aside. Yet time and again, Mr. Trump — who refers to him as “Rog” — would turn to his old friend.
Ultimately, the question from the indictment is what the campaign — and Mr. Trump — may have known about Mr. Stone’s correspondence.
In Mr. Pehme’s documentary, Mr. Manafort was filmed at length discussing how intertwined Mr. Stone is with the president. “It’s hard to define what’s Roger and what’s Donald,” Mr. Manafort says in the film. “They both see the world in a very similar way.”
Speaking outside federal court, appearing unbowed, and even to be taking pleasure in the spectacle, Mr. Stone said he would not testify against the president. “I am one of his oldest friends,” he said. “I am a fervent supporter of the president.”