The relationship, rocky at times, has lasted decades. Now comes a high-profile indictment — and fresh pressure.
That Roger Stone was arrested on Friday did not come as a surprise to Roger Stone.
The self-proclaimed Republican "dirty trickster" had been saying publicly that he expected to be indicted and loudly proclaiming his innocence for months — long before he was finally indicted by a federal grand jury as part of special counsel Robert Mueller's probe of alleged collusion by the Trump campaign with Russia, and possible obstruction by the president.
Now the pugnacious pal of President Donald Trump has been hit with obstruction, giving false statements and witness tampering charges that, if he's convicted, means he could conceivably spend his golden years wearing prison blues instead of his signature custom suits. He might even be forced to wear socks, which he reportedly loathes.
So far the 66-year-old political consultant, who lives by the motto "Admit nothing, deny everything, launch counterattack" and has been a flamboyant if quirky fixture on the Washington scene for years, has given no sign that might cut his losses and turn on Trump.
"I will never testify against Trump," Stone declared in December.
"Nice to know that some people still have "guts!" Trumped tweeted afterward.
Stone carved out a unique spot in the political landscape long before he crossed paths with Trump, who first employed him as a lobbyist for his casino business. He is credited with planting the idea of running for president in Trump's head.
"I'm an agent provocateur," Stone admitted in "Get Me Roger Stone," a Netflix documentary that featured Trump and another high profile figure who has been caught in Mueller's net, former Trump campaign manager Paul Manafort.
Born Aug. 27, 1952 in Connecticut, Stone recalled in an interview that he found his calling around age 8 during the 1960 presidential campaign that pitted John F. Kennedy versus Richard Nixon. He said his school held a mock vote and that year he was for the Democrat.
"I remember going through the cafeteria line and telling every kid that Nixon was in favor of school on Saturdays," Stone told the Washington Post. "It was my first political trick."
JFK cleaned Nixon's clock in that school election. But a few years later Stone was handed Barry Coldwater's "The Conscience of a Conservative" and he switched to the Republican side.
By 1972, Stone was working for Nixon's re-election campaign. His official title was scheduler. His real job, he said, was dispatching people to spy on Hubert Humphrey's campaign.
"By night, I'm trafficking in the black arts," he freely admitted in an interview that he wound up posting on his website.
While Stone is best known for helping engineer the political rise of Trump, it was Nixon that literally got under his skin — he sports a tattoo of the 37th president on his back, between his shoulders blades.
Stone was outed by newspaper columnist Jack Anderson as a "dirty trickster" after Nixon resigned, but he always maintained he never did anything illegal during Watergate. He also helped pioneer ways of getting around campaign contribution restrictions by helping found the National Conservative Political Action Committee in 1975.
He worked for successful presidential campaigns of George H.W. Bush and Ronald Reagan and later opened a mega-successful Washington D.C. lobbying firm with Manafort that included GOP political strategist Lee Atwater.
Manafort is now sitting in jail and supposed to be cooperating with the Mueller investigation. Atwater is dead.
Not only did Black, Manafort & Stone work for Republicans, they also earned a fortune representing brutal dictators like Ferdinand Marcos of the Philippines and Mobutu Sese Seko of the Republic of Congo.
Rupert Murdoch's News Corp. and the Tobacco Institute also were clients. And, starting in the 1980s, so was Trump.
It was another take-no-prisoners personality, attorney Roy Cohn, who introduced Stone to Trump in 1979, with the two quickly becoming fast friends.
In addition to their permanent tans and suspiciously thick hair, Stone and Trump also had racy reputations.
Stone resigned from then-Sen. Bob Dole's presidential campaign after the National Enquirer reported that the strategist and his second wife, Nydia Bertran Stone, had placed ads in swinger magazines. He later served as campaign manager for "Manhattan Madam" Kristen Davis, who helped take down former New York Gov. Eliot Spitzer.
Davishas also been interviewed by Mueller's team.
But Stone and Trump also rubbed each other the wrong way at times, and Trump bristled at the notion that Stone was his Svengali.
"Roger is a stone-cold loser," Trump said around the time he was considering running for president in 2000. "He always tries to take credit for things he never did."
Still, the Stone/Trump friendship endured. Stone, who now lives mostly in Miami, was a frequent visitor to Trump's Florida getaway Mar-a-Lago.
When Trump ran for president in 2016, Stone served for a time as an adviser and knee-capper of Trump critics. He made headlines for launching bigoted broadsides against TV commentator Roland Martin and fanning unsubstantiated adultery allegations against GOP rivals like Sen. Ted Cruz of Texas.
Stone also became Trump's ambassador to fringe right figures and bogus conspiracy mongers like Alex Jones, on whose "Info Wars" program he was a frequent guest.
"I predicted for many months that I would be framed on some processed charge," Stone told Info Wars in a phone call after his court appearance Friday.