Just as he operated on the fringes of Donald Trump’s campaign, so too did Roger Stone – the outrageous self-styled master of the dark political arts – hover at the edge of the investigation into Russian election meddling.
He was often dismissed as a flamboyant distraction as special counsel Robert Mueller’s probed for signs of collusion between the campaign and Moscow.
That changed on Friday. Mr Stone, a long-time informal adviser to Mr Trump, was arrested in a dawn raid and appeared shackled in court on charges brought by investigators who allege he sought stolen emails from WikiLeaks that could damage Hillary Clinton while co-ordinating with senior campaign officials.
The indictment does not say who else knew of Mr Stone’s alleged role but for the first time it reveals that prosecutors believe additional people around the president knew of his attempt to contact Julian Assange, the WikiLeaks founder.
But he was not charged with conspiring with WikiLeaks. He faces seven counts that include tampering with witnesses and making false statements.
Mr Stone addressed the media on the steps of Fort Lauderdale courthouse in which he appeared to declare his innocence.
“I’ve always said the only thing worse than being talked about is not being talked about,” he said with a smile.
Mr Stone said that he “categorically” did not work with Moscow and said he would not turn against Mr Trump, one of his oldest friends.
“Any error I made in my testimony would be both immaterial and without intent,” he said.
The White House moved quickly to distance itself from the arrest.
"The charges brought against Mr Stone have nothing to do with the president, nothing to do with the White House," spokeswoman Sarah Sanders told CNN. "The president did nothing wrong."
However, court documents hint that Mr Mueller is following a trail of links between senior figures.
“After the July 22, 2016, release of stolen (Democratic National Committee) emails by Organisation 1, a senior Trump Campaign official was directed to contact Stone about any additional releases and what other damaging information Organisation 1 had regarding the Clinton Campaign," prosecutors wrote.
"Stone thereafter told the Trump Campaign about potential future releases of damaging material by Organisation 1.".
Organisation 1 refers to WikiLeaks and speculation is rife about who had the power to direct a senior campaign official.
The papers say that Mr Stone was contacted by other senior officials who wanted to know what else was coming.
He had publicly claimed to have been in contact with WikiLeaks and suggested he knew that John Podesta, Mrs Clinton’s campaign chairman, was in its sights. He tweeted that it would soon be Mr Podesta’s “time in a barrel” before his hacked emails were released.
Mr Stone has since denied any prior knowledge.
Opponents insisted he was the key to understanding how Russia tried to exert influence by stealing and leaking Democratic emails, but Mr Trump’s supporters suggest he was guilty of only empty boasts.
However, it emerged last year that before the election Mr Stone was communicating on Twitter with Guccifer 2.0, an account used by Russian operatives.
The new indictment also details a Congressional inquiry in September 2017 at which Mr Stone was quizzed about his claims that he had no emails concerning hacked documents.
“That is correct. Not to my knowledge,” he said.
But according to the charges, he was in possession of dozens of emails and text messages discussing WikiLeaks.
The indictment also includes how Mr Stone used language evoking mob bosses – even quoting a character in the Godfather film – as he called an unnamed associate facing FBI inquiries “rat” and a “stoolie" in messages laced with profanities.
It marks the latest twist in an extraordinary career. Mr Stone was one of the most colourful and controversial of the figures that coalesced around Donald Trump’s misfit campaign.
He has long styled himself a “dirty trickster”, willing to do anything to make his point, in a public image that may have helped prosecutors as they waded through reams of bold, boastful public statements.
Mr Stone once claimed to have rigged a mock election at high school so that Richard Nixon triumphed over John F Kennedy.
But his career proper began as a low-level aide to Nixon's 1972 presidential campaign and he is famous for having a tattoo of the late, disgraced president on his back.
"By night, I'm trafficking in the black arts. Nixon's people were obsessed with intelligence," he once said in an interview with the conservative Weekly Standard magazine.
He turned to the lucrative world of lobbying in the 1980s, working with Paul Manafort, who later became Mr Trump's campaign chairman and has since been convicted of tax evasion and fraud. But Mr Stone also continued to act as a political adviser.
He was one of the first to sign up when his friend launched his campaign in 2015 but soon quit, or was fired, depending on which account you believe.
Right wing commentators insisted that the new indictment did not amount to evidence of collusion.
But critics of the administration said Mr Stone’s role cut to the heart of the matter.
Richard Stengel, former undersecretary of state in the administration of Barack Obama, said on Twitter: “Roger Stone represents a straight line between Richard Nixon and Donald Trump and it stands for everything that is wrong with American politics.”