By Alex Thomas

Of all of the Trump associates that have shaped Donald’s trajectory to 1600 Pennsylvania Avenue, 66-year-old Roger Stone is… well, one of the nastier ones. Stone’s is a name you’ll see scattered across newspaper stories from the past few decades, dating back to mentions of his relationship with Richard Nixon and slowly climbing until he became the center of the story itself. During his long career, Stone grew close with Donald Trump and for years had encouraged him to run for president before Trump finally got serious about an Oval Office attempt.

In the Nixon administration, Stone cut his teeth as a “dirty trickster” — among other devious acts, he contributed to the demise of a Nixon opponent, Rep. Pete McCloskey, in the 1972 Republican presidential primaries by posing as a socialist, and then tipping off a New Hampshire newspaper about the move. In the polls, McCloskey earned only 11 percent of the vote in the New Hampshire primary. These below-the-belt tricks even have a name in politics: ratfucking. And Roger Stone proved to have a gift for them. Richard Nixon became an icon to Stone, to the extent that Stone has the former president’s face tattooed on his back.

Stone later became close with Paul Manafort, the eventual chairman Trump's 2016 presidential campaign. In the ’80s, the pair put together a lobbying firm called Black, Manafort, and Stone. The firm eventually earned a reputation for doing PR work for brazen dictators of countries struggling with democracy like the Phillipines and the Republic of Congo. At some point in that decade, the firm began representing Donald Trump.

When Black, Manafort, and Stone broke up, Manafort continued to represent dictators including Viktor Yanukovych in Ukraine, while Stone went mainstream. He worked on Bob Dole’s unsuccessful presidential campaign in 1996.

Over the years, Trump and Stone continued to circle each other, it seems waiting for the moment when they would capitalize on their talents. Stone was Trump’s longtime fan; he regularly encouraged the real estate mogul to run for president but it’s unclear if that feeling was reciprocated. In 2008, Trump told the New Yorker, “Roger is a stone-cold loser,” despite Stone’s role as an adviser to the 2000 presidential run Trump considered.

Finally, in the summer of 2015, Trump came down the escalator in his Manhattan tower and announced that he would run for president. Stone came along for the ride, once again joining as an adviser, but left his role after only a few months. (Unsurprisingly, Trump claims he fired Stone; Stone says that he left voluntarily.)

After leaving the campaign, Stone became connected with other controversial figures, most notably, WikiLeaks and its founder, Julian Assange. Though Stone now claims that he has never spoke to Assange, in August of 2016, he told a group of Florida Republicans, “I've actually communicated with Julian Assange.” In 2017, Stone was subjected to a closed-door interview with the House Permanent Select Committee on Intelligence about his connections to Assange's organization and the Trump campaign. The Atlantic has since reported that Stone and WikiLeaks spoke to one another via Twitter.

And based on Stone's tweets from the time, he appears to have had advanced knowledge in 2016 of when WikiLeaks was preparing to “dump” emails that were hacked from the Clinton campaign and the Democratic National Committee. That crosses a few lines. Every American intelligence agency has said that the emails were hacked by Russian actors and sent to WikiLeaks in an effort to undermine Hillary Clinton. This connection has proven of interest to special counsel Robert Mueller.

Last week, Stone was arrested by FBI agents in a pre-dawn raid at his Florida home. Mueller charged Stone with seven counts that include witness tampering and lying to Congress during that 2017 interview. He’s said that the process of that arrest was unnecessary and that he would have turned himself in, but it’s hard to imagine Stone being taken in by the feds in any way other than a raid in the Fort Lauderdale darkness. He certainly would have preferred those tactics if any of his adversaries were to be taken in by the authorities. When Stone appeared outside the courthouse that same day, he was grinning and mimicking his idol, Nixon. As he began to give a statement, the crowd chanted, “Lock him up.”

In the charging documents, the special counsel said that Stone was in communication with a top official in the Trump campaign and was tipping them off about WikiLeaks’ email dumps. Stone maintains that he’s innocent, and today (January 29), in a Washington federal court, he pleaded not guilty to the charges against him.

The next chapter in Stone’s long career in and around politics will be an arduous process in which he’s forced to defend himself against the charges. The special counsel has defeated everybody who has been charged: Mueller’s team has already sent Stone’s one-time colleague Manafort off to jail for tax fraud, and Trump’s former national security advisor Michael Flynn is currently awaiting sentencing.

The odds are not in Stone’s favor, and that doesn’t look good for Trump.

The investigation and trial is sure to shed a light on the communications between Stone, WikiLeaks, and the Trump campaign. Mueller’s team said in the charging documents that they have the paper trail showing those communications. If the special counsel can prove that Stone was coordinating with a top Trump campaign official during his communications with WikiLeaks, there could be further implications for Trump's team.

Unfortunately for the president, Stone was a key part of his campaign. Most of the allegations that Trump is facing from Mueller's investigation — like possible collusion with Russian-state actors — date back to the campaign and, even more specifically, to the earlier days of the campaign. During that time, Stone was directly associated with Trump.

The possible crimes have evolved, with most pundits suggesting that the more substantial charges that Trump could be facing are related to obstruction of justice. Specifically, the theory that the president has tried to cover his tracks for possible crimes committed during the campaign. Since Stone was a member of that campaign, and has been at least loosely tied to WikiLeaks, efforts that Trump made to put investigators off that scent could implicate Stone.

And as for Stone, this might just be the last act for the dirty trickster.