Roger Stone, the Trump adviser and self-proclaimed dirty trickster arrested on Friday at his home in Florida, is the latest figure indicted in the Mueller probe investigating Russian interference in the 2016 election.

But long before his present appearance on the national stage, Mr. Stone perfected his bare-knuckled brand of political warfare in New York.

Back in high school in Westchester County in the late 60s, Mr. Stone said he orchestrated the ousting of the student president and elevated himself.

“I built alliances and put all my serious challengers on my ticket,” Mr. Stone told The Times in 1999. “Then I recruited the most unpopular guy in the school to run against me. You think that’s mean? No, it’s smart.”

Other highlights from Mr. Stone’s activities in New York:

1980: He helped run Ronald Reagan’s presidential campaign in New York and Connecticut. The Times called him “equally adept at cajoling or threatening.”