WASHINGTON — For nearly 50 years, Roger J. Stone Jr. taunted the political gods of fate, unleashing a torrent of dirty tricks on behalf of President Trump and his other well-connected clients and daring his adversaries to come after him, certain that the pursuit would make him richer and famous.
On Thursday, history may have finally caught up with him. But as is often the case with Mr. Stone, there may be an escape clause.
In a Washington courtroom, the dapper Republican political consultant — who once declared, “I revel in your hatred, because if I weren’t effective, you wouldn’t hate me” — was sentenced to more than three years in prison for trying to help Mr. Trump dodge accusations that his 2016 campaign conspired with the Russians.
Whether Mr. Stone, 67, will actually spend years behind bars may depend on the durability of his long and tumultuous friendship with Mr. Trump, who strongly hinted on Thursday that he might pardon his on-again, off-again adviser. “I’m going to let this process play out,” Mr. Trump said, but he added that “Roger Stone and everybody has to be treated fairly. This has not been a fair process.”
“He’s a smart guy,” the president went on. “He’s a little different. But those are sometimes the most interesting.”
Interesting, yes.
Mr. Stone, who came of age during Richard M. Nixon’s political ascent — and now has a tattoo of Nixon’s face between his shoulder blades — viewed his label of “dirty trickster” as less an insult than as a point of pride. Long before the F.B.I. raided his Florida home last year to accuse him of obstruction and lying, Mr. Stone embraced the power that came with campaign manipulation.
In 1972, he posed as a socialist making contributions to the campaign of Nixon’s Republican primary opponent. (He sent a receipt for the donation to a New Hampshire newspaper to create a scandal.) Later, after it became public that Mr. Stone had hired someone to infiltrate the presidential campaign of Senator George McGovern, he was fired from his Capitol Hill job working for Senator Bob Dole.
Mr. Stone’s career in the shadows was influenced by his introduction in the late 1970s to Roy Cohn, who was Senator Joseph McCarthy’s red-baiting protégé. Mr. Stone would come to refer to Mr. McCarthy as “a master of public relations,” embracing his bare-knuckle tactics and political dark arts. (Mr. Cohn, Mr. Trump’s longtime lawyer, first introduced Mr. Stone to Mr. Trump.)
Inspired by Mr. Cohn’s influence, Mr. Stone adopted rules he would live by for decades: attack, attack, attack. Never defend. Admit nothing, deny everything, counterattack.
For the next 20 years, Mr. Stone honed his skills in the raucous politics of a New York dominated by bigger-than-life politicians and the tabloid newspapers that lavishly covered them. Mr. Stone became bigger than life himself, driving Jaguars, wearing flamboyant suits and dishing out delectable quotes.
“The key to a good martini is you have to marinate the olives in vermouth first,” he once told The New Yorker, explaining his drink of choice. “Nixon gave me the recipe. He said he got it from Winston Churchill.”
It wasn’t always easy to separate Mr. Stone’s boasts from reality. When he was caught leaving a profanity-laced voice message for the father of Eliot Spitzer, then the attorney general in New York, Mr. Stone claimed he couldn’t possibly have placed the call because he was attending the Broadway show “Frost/Nixon” that night. The show wasn’t even playing that evening.
In the 1980s, Mr. Stone briefly became part of the Washington establishment when he joined Paul Manafort, the former Trump campaign chairman now in prison for financial fraud, to help create the powerhouse Republican consulting firm of Black, Manafort and Stone. An early client was Mr. Trump, then a celebrity real estate mogul in New York. In 1987, Mr. Stone tried to woo Mr. Trump into a race against a possible challenger to Mario Cuomo, the popular Democratic governor of New York, but Mr. Trump said no.
The partnership was not always a love affair. Mr. Trump once called Mr. Stone “a stone-cold loser.” For a while, Hillary Clinton became Mr. Stone’s obsession: In 2008, he founded an anti-Clinton group; critics quickly noticed that the first letters of the group’s four-word name detailed a crude epithet.
In the run-up to the 2012 campaign, it was Mr. Trump who was on Mr. Stone’s mind as Mr. Trump toyed with and then rejected the idea of challenging Barack Obama for the presidency. Four years later, in 2015, Mr. Stone was again among the handful of advisers who told Mr. Trump that if he wanted the White House, 2016 was probably his last chance. He served as a consultant for a few months on the campaign, but when Mr. Trump concluded that Mr. Stone was more interested in promoting himself, he was out.
“I terminated Roger Stone last night because he no longer serves a useful function for my campaign,” Mr. Trump told The Washington Post at the time. Later, in a tweet, Mr. Stone disputed Mr. Trump’s assertion that he was fired. “I fired Trump,” he wrote.
But if he was no longer on the inside, Mr. Stone was determined to not be completely out of Mr. Trump’s orbit. In the final months of the 2016 campaign, Mr. Stone sought to obtain information about emails that had been stolen by Russia from the computers of the Democratic National Committee and ended up in the possession of WikiLeaks. The emails released by the website helped damage Mrs. Clinton’s campaign.
It was Mr. Stone’s involvement in that affair that set the stage for his final downfall. Prosecutors proved to a jury that he had lied to investigators under oath and tried to block the testimony of another witness — an effort for which a federal judge on Thursday said he should spend 40 months in prison.
Or perhaps not. Just hours later, Mr. Trump appeared before a group that helps former convicts re-enter society. He repeatedly defended Mr. Stone, calling him a “good person” and lashing out at the forewoman of the jury that convicted him, accusing her of being politically biased against him.
For a moment, it seemed as if Mr. Trump might use the opportunity to pardon Mr. Stone on the spot. He did not. But he left little doubt that he viewed Mr. Stone as someone who shared the same grievances that Mr. Trump has nursed since the early days of his presidency.
“We will watch the process and watch it very closely,” Mr. Trump told the audience of former convicts. “And at some point I will make a determination.”