1976–80: Stone works on Ronald Reagan’s two presidential campaigns

In 1976, Stone joined Reagan’s first failed presidential bid, working as his “youth director.” The following year, at 24 years old, Stone was elected chairman of the Young Republicans, a political organization for conservatives ages 18 to 40. The chairmanship had clout in conservative circles; the Young Republicans’ support was crucial to Barry Goldwater’s presidential nomination in 1964. Stone’s friend from the College Republicans, Paul Manafort, managed his campaign. Decades later, Manafort would become chairman of Trump’s 2016 presidential bid, and would also be indicted by the special counsel. Both men were from Connecticut, and as our colleague Franklin Foer wrote last March, they shared “an affection for finely tailored power suits, and a deeper love of power itself.”

By 1980, Stone had made crucial contacts in Reaganworld, and coordinated the Reagan campaign’s efforts in the Northeast that year, during the California governor’s second run at the White House. He worked closely with the Reagan adviser Roy Cohn.

1980: Stone meets Donald Trump

Cohn introduced Stone to his friend and protégé Donald Trump, then a private businessman. At Stone’s urging, Trump, who was in his 30s, became a major donor to Reagan’s second presidential campaign. The two men hit it off—the start of a tumultuous relationship that spanned both business and politics over the next three decades.

Read: Trumpworld follows a Godfather script—literally

1980: Stone helps establish a lobbying firm with Manafort

After Reagan won the White House, Stone founded one of Washington’s first major lobbying firms with friends from his Young Republicans and campaign days: Charles Black and Manafort. As Foer has written, Black, Manafort, and Stone pioneered a new type of influence peddling that was hardball and morally dubious. One of their first clients: Trump and the Trump Organization, his family business.

1998–99: Stone helps Trump lay the groundwork for his first presidential bid

Trump had been toying with the idea of running for president for more than a decade, but in 1998 he decided to take some concrete steps. The first: asking Stone to find “the most eminent hack writer in America” to ghostwrite a book for him.

The next year, when Trump explored a bid for president as a member of the Reform Party, he chose Stone to head his exploratory committee. In later years, Trump would downplay Stone’s role in the campaign. “He always tries taking credit for things he never did,” Trump told The New Yorker in 2008. Nonetheless, Stone remained an adviser and confidant of Trump for the next decade.

2007: Stone is caught threatening the elderly father of a political rival

Stone was forced to resign from a position consulting for New York State’s then–Senate Majority Leader Joseph L. Bruno after allegations emerged that he left an intimidating voicemail for the 83-year-old father of New York Governor Eliot Spitzer. In the anonymous voicemail, he threatened to prosecute the elder Spitzer if he didn’t implicate his son in illegal activity. Stone denied leaving the message, but those who know him have identified his voice on the recording. “They caught Roger red-handed lying,” Trump said in the 2008 New Yorker profile. “What he did was ridiculous and stupid. I lost respect for Eliot Spitzer when he didn’t sue Roger Stone for doing that to his father, who is a wonderful man.”