He attended George Washington University but didn't graduate because he got into politics, working with Republican candidates for more than 40 years, according to The New Yorker.
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He was only 19 when Watergate happened, and he, under the name Jason Rainier, made contributions to Pete McCloskey, who was challenging President Richard Nixon for the Republican nomination. Stone, as Rainier, made the contributions through the Young Socialist Alliance and then released the receipt to a newspaper to show that McCloskey was a left-wing candidate, according to The New Yorker.
Stone also hired another person to work in George McGovern's Democratic presidential campaign. Both events were uncovered during the Watergate hearings in 1973. He lost a job on the staff of Republican Bob Dole because of the hearings and started the National Conservative Political Action Committee, which backed Republicans Chuck Grassley in Iowa and Dan Quayle in Indiana.
Stone also worked twice on the Republican presidential campaigns of Ronald Reagan -- once in 1976, when Reagan didn't win, and again in 1980, when he did -- then as political director for New York, New Jersey and Connecticut, The New Yorker reported.
After Reagan took office, Stone stayed in the private sector, creating a political consulting and lobbying firm that went under different names, including Black, Manafort, Stone & Atwater.
The firm worked for corporations like Rupert Murdoch's News Corp. to lobby former co-workers in the Reagan campaign who held jobs in the administration. It also served clients like Philippine President Ferdinand Marcos, The New Yorker found.
Focusing more on political campaigns as a solo entity instead of lobbying as part of a group, Stone worked as a senior consultant for the successful campaign of George H.W. Bush and worked three campaigns for Republican Pennsylvania Sen. Arlen Specter. He also ran unsuccessful campaigns for Dole’s 1996 quest for president.
He was brought in when the 2000 presidential recount started in Florida. He played the political game on radio stations in southern Florida, saying that the recount was Al Gore's left-wing power grab, The New Yorker reported. His efforts, along with other Republican assets, empowered George W. Bush's Republican supporters to protest the second recount. Stone wanted, and got, the recount in Miami shut down in what became the "Brooks Brothers riot," The Washington Post and The New Yorker reported.
Stone also worked on the younger Bush's re-election campaign. It is believed documents obtained by CBS News that showed that Bush got out of military service for Vietnam were actually fake and that Stone was the person who created the documents, The New Yorker reported.
Stone was one of President Donald Trump's panel of long-time advisors, The Washington Post reported. He was connected to Trump when the now-president floated the idea of running in 2000.
Then, Trump said, "Roger is a stone-cold loser," who "always takes credit for things he never did," according to The New Yorker.
Despite the harsh words then-private sector member Trump had for Stone, he used Stone for his campaign not once, but twice, teaming up in 2011 when Trump toyed with, but eventually decided against a presidential run. They went their different ways in August 2015, the Times reported.
But who pulled the plug on Stone's tenure on the Trump campaign? Stone said he resigned and Trump's campaign officials said he had been fired, The New York Times reported.
Trump said of the firing, "I hardly ever spoke to the guy; he was just there. He played no role of any kind," the Times reported in 2015.
But Stone was listed on Federal Election Commission filings as being on the campaign payroll and he used Twitter to defend Trump during the campaign, according to the Times.
What is his connection to Trump?
Stone has been scrutinized for having ties to WikiLeaks by using an associate as an intermediary between himself and people associated with WikiLeaks, CNN reported.
Stone spoke about having "back channel communications" with Julian Assange, the founder of WikiLeaks, during the campaign. Stone later said the "back channel" was really a New York radio host, Randy Credico, who allegedly shared only information gleaned from interviews with Assange, CNN reported.
Stone also predicted releases of information by WikiLeaks in the final days of the campaign between Trump and his Democratic challenger, Hillary Clinton, CNN reported.
Stone said in a column for Breitbart, the website run by former Trump campaign adviser Steve Bannon, that it wasn't the Russians who hacked the servers containing the emails leaked by WikiLeaks, but it was actually a hacker who went by the name Guccifer 2.0.
Despite Stone's assertions in the column, some have linked Guccifer 2.0 to Russian web services, Foreign Policy reported.
In July 2016, the Times reported that intelligence agencies had "high confidence" that the Russian government was behind the email leaks and that Guccifer 2.0 was in reality an agent of the Russian military intelligence service, or GRU.
Mueller's team is investigating whether there were other connections between Stone and WikiLeaks. That connection could come in the form of Jerome Corsi, another associate of Stone's who said this week that he expects to be indicted by Mueller for "giving false information to the special counsel or to one of the other grand jury," CNN reported.
If Corsi's prediction comes true, he could face charges from perjury to making false claims and even obstruction of justice, all related to false statements he made about his alleged connection between WikiLeaks and Stone, CNN reported.
Stone, however, said he was truthful in previous testimony before a congressional panel.
"My attorneys have fully reviewed all my written communications with Dr. Corsi," Stone wrote in a statement to CNN. "When those aren't viewed out of context they prove everything I have said under oath regarding my interaction with Dr. Corsi is true."
Stone went on to write, “I stand by my statement to the House Intelligence Committee and can prove it is truthful if need be. I have passed two polygraph tests administered and analyzed by two of the nation's leading experts to prove I have (been) truthful.”
Corsi said Stone warned that there would be trouble for Clinton campaign Chairman John Podesta after Corsi published an article for InfoWars. After Stone's statement, WikiLeaks released thousands of hacked emails from Podesta, CNN reported.
Stone tweeted "it will soon the Podesta's time in the barrel" six weeks before WikiLeaks published the emails, The Washington Post reported.
Stone said he did not tell Trump that WikiLeaks was going to release the hacked emails and denied working with Russia, CNN reported.
But Stone did say in a recent opinion piece for The Daily Caller, that he emailed Bannon during the campaign, CNN reported. Stone, in the column, clarified that the information he shared with Bannon was publicly available.
Stone said the statements he made during the campaign were exaggerations or tips only and that he didn't know details of WikiLeaks' plans before the document drops, the Post reported.
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