Buddy Cianci was elected six times to the mayoralty of Providence, Rhode Island, and had to resign twice, each time after a felony conviction. PHOTOGRAPH BY BRIAN SNYDER / REUTERS

“Be careful,” the notoriously thuggish Mayor Vincent Albert (Buddy) Cianci, of Providence, Rhode Island, told an officer of that city’s notoriously sniffy-patrician University Club, back in 1998. “The toe you stepped on yesterday may be connected to the ass you have to kiss today.”

That is a teaching that would fit handsomely on a tombstone for Cianci, who got himself elected for the first time, in 1974, as an anti-corruption candidate, and died in that city Thursday morning, at the age of seventy-four, with a reputation as one of America’s most thoroughly corrupt political personalities. In the intervening years, he served as mayor twice—in a scandal-plagued first round, from January, 1975, to April, 1984, and again from January, 1991, to September, 2002—and both times was forced to resign after being convicted of felonies. He was Providence’s first Italian-American mayor (breaking a long Irish-American lock on power); he was its first Republican mayor since the forties (although, after his first two terms, he disaffiliated and declared himself an independent); he was the longest-serving mayor in the history of the city (and one of the longest-serving mayors of any American city); and, as the patriarch of Providence’s transformation from a desolate post-industrial, Mafia-dominated wasteland to a vibrant, thriving, model of new urbanism, a cultural and culinary destination city with falling crime rates and rising property values, Cianci was deservedly one of the most celebrated American city fathers of our times—except, of course, for his penchant for running afoul of the law.

“Yeah, I punched a guy in the mouth for fucking my wife. But look at the city,” Cianci told me, in the summer of 2002, referring to his first conviction (for torturing his ex-wife’s boyfriend with, among other things, a fireplace log and a burning cigarette), a case in which he pleaded no contest. I was in Providence that summer to watch him fight the charges that led to his second conviction; Cianci’s attitude–I may be a fallen human, but how about this rising city?—was widely shared by his constituents, who had, after all, elected him six times, with no illusions that he was Mr. Clean. By the time of his trial, many felt they’d had enough of his act, and could live without the embarrassments that came with it, so there was no great lamentation when he was finally found guilty and sentenced to five years in federal prison.

Still, the case against Cianci was a shabby business—a mess of small-time graft charges brought together and pinned on him under the auspices of the Racketeer Influenced and Corrupt Organizations (RICO) Act, which was designed to take down organized-crime godfathers by holding them accountable for the acts of flunkies—even, or especially, when no direct evidence could be found linking the boss to any misdeed. The government has to prove only that there is a criminal syndicate, that so-and-so is involved, that his underlings have committed such-and-such crimes, and the chief is guilty. It is an instrument for proving guilt circumstantially—by association. So the conceit of the F.B.I. and the prosecutors in the Cianci case was to call Cianci’s City Hall the “criminal enterprise,” and then to nail him for the embarrassingly petty shakedowns and favor-selling of his more unsavory aides-de-camp.

The F.B.I. hyped its sting, which involved harnessing a vindictive and violent local businessman named Antonio Freitas with recording equipment and sending him around to thrust bribes at city officials, by naming it Operation Plunder Dome. But, in the courtroom, day after day for week upon week of that hot, humid Rhode Island summer, it was obvious that the government had no hope of making a single charge stick to Cianci. The judge, Ernest Torres, an impeccable figure, made no secret of his feeling that he had to find Cianci guilty because RICO—rather than the facts—gave him no choice.

Cianci was no innocent, and they got him, but they didn’t get him good. One couldn’t escape the feeling that the government’s case against him was as corrupt as anything he or his crooked cronies were charged with. The F.B.I.’s hero in the matter, Freitas, was born in Portugal under the dictatorship of Antonio Oliveira Salazar, whom he spoke of as a “very nice guy,” while he told me that Cianci was akin to both Saddam Hussein and Adolf Hitler. Freitas, who had been arrested several times for domestic violence, also told me how he fantasized about smashing his ex-wife’s teeth in with a pipe, and how spectacularly powerful he felt after bringing Cianci down. What remained to make Providence great, he claimed, was to deal with the people on welfare (“it’s blacks, mostly”) and rats.

Like many of the great folkloric figures of American history, Cianci was equal parts public servant and rogue, and the two qualities are inextricably entangled. He was about as complete a combination of colorful and effective as they come in our civic culture. But was he really among the most corrupt?

Was he more corrupt—or more corrupting to our democratic ideals—than that other Republican turned independent mayor, Michael Bloomberg, who is said to be incorruptible because he is so stupefyingly rich, but who used his power to persuade the City Council to overrule two voter referendums in favor of term limits and have a third term at New York’s City Hall? Was he more corrupt than Rahm Emanuel, of Chicago, whose City Hall covered up the police killing of a young black man? Should we really leave our judgment of whom we call corrupt to our courts?

With the news of his death arriving amid the 2016 Presidential primaries—a political carnival more corrupt (in the core sense of the word, meaning rotten, and in the sense of money skewing politics) than anything he ever presided over—Buddy Cianci seems more of a figure of yore than an ogre for the ages. When I asked him, shortly after his 2002 conviction, whether he thought his line about the toes you step on and the asses you kiss was the way politics work, he said no, that’s life.