Sid Davidoff, a gutsy and gregarious lawyer who joined John V. Lindsay’s audacious, youth-driven campaign for mayor of New York in 1965 and, after victory in the election, became one of his chief lieutenants in City Hall in trying to calm the city’s volatile neighborhoods, died on Sunday in the Dominican Republic. He was 86.
His wife, the newspaper columnist and author Linda Stasi, said he died of sepsis in a hospital near his vacation home in Punta Cana, where he was staying while recovering from shoulder surgery. He lived on the Upper East Side of Manhattan.
Mr. Davidoff was in his mid-20s, a brash, barrel-chested former college wrestler, when he joined Mr. Lindsay’s upstart liberal-Republican challenge to New York’s sclerotic Democratic clubhouses and entrenched power brokers.
The two men shared a commitment to reviving what they judged to be a weary city in crisis. (The campaign’s unofficial motto, coined by the columnist Murray Kempton, crowed of Mr. Lindsay: “He is fresh and everyone else is tired.”)
But they made an improbable partnership. Lindsay’s mother’s Protestant family had been in New York since the 1600s, and, in Congress, he had represented a district that included much of the affluent Upper East Side. Mr. Davidoff was the Brooklyn-born son of a Russian Jewish immigrant who owned a candy store in Queens.
“A more unlikely coupling you couldn’t possibly imagine,” Gordon J. Davis, a Lindsay administration alumnus and later New York City’s parks commissioner, said in an interview.
Mr. Davidoff’s knowledge of the city’s streets — gleaned, in part, from driving a truck, selling the insecticide DDT to tenement dwellers, waiting tables and booking rock ’n’ roll bands — paid off when he shepherded Mr. Lindsay around during the 1965 campaign.
Running on the Republican and Liberal lines, Mr. Lindsay won a tight plurality victory in November against Abraham D. Beame, a Democrat who would succeed him as mayor in 1974, and the political commentator William F. Buckley Jr., the Conservative Party candidate.
Mr. Davidoff’s eventual, unassuming title, assistant to the mayor, belied his outsize role as patronage dispenser, bodyguard, advance man and all-purpose fixer. He worked largely behind the scenes with another unsung aide, Barry Gottehrer, with a mandate to anticipate local grievances and quell unrest amid racial tensions, antiwar protests, municipal strikes and other upheavals of the time.
They did that in part by enlisting radical community groups, recruiting gang members to serve as street-level intermediaries in troubled neighborhoods, and turning to other unconventional partners.
Though the men’s methods were sometimes unorthodox and did not always endear them to the police — they were accused of coddling Black militants and consorting with organized crime figures — they helped keep New York cool during the proverbial long, hot summers of the late 1960s, when other American cities burned.
Not all was calm. In 1968, Mr. Davidoff was sent to mediate the raging dispute between Columbia University and student protesters who had occupied several university buildings. He failed to resolve the conflict, though he negotiated the release of a dean who was being held captive inside occupied Hamilton Hall.
In May 1970, Mr. Lindsay ordered the American flag above City Hall to be lowered to half-staff to honor the students who were shot and killed by National Guard troops as Vietnam War protests flared at Kent State University in Ohio.
Cheered on by construction workers, a mail carrier defiantly raised the flag back to full staff. Mr. Davidoff — ever fearless, even cocksure — climbed to the roof and lowered it again. With the rowdy crowd threatening to storm City Hall, Deputy Mayor Richard Aurelio ordered the flag raised for good.
Mr. Davidoff worked indefatigably to re-elect Mr. Lindsay, who ran in 1969 on the Liberal Party line after losing the Republican primary to John J. Marchi. Mr. Lindsay won another plurality victory in the general election. In 1972, Mr. Davidoff helped spearhead the mayor’s abortive campaign for the Democratic presidential nomination, a year before Mr. Lindsay left City Hall, his grand ambitions having largely gone unfulfilled.
At the Senate Watergate hearings that year, John Dean, the former White House counsel, revealed that Mr. Davidoff was on a list of political enemies that had been drafted by the White House to single out targets for tax audits and other reprisals by federal agencies.
Ranked 12th on the list of 20, he was identified as “Lindsay’s top personal aide: a first class S.O.B., wheeler-dealer and suspected bagman,” referring to an intermediary who solicits bribes.
“Positive results,” it continued, meaning success in smearing Mr. Davidoff, “would really shake the Lindsay camp and Lindsay’s plans to capture youth vote.”
“Davidoff,” it concluded, was “in charge.”
In 2024, Mr. Davidoff wrote an essay for MSNBC about his appearance on the enemies list. “Though in many ways it remains my proudest moment,” he observed, “the fallout was difficult to deal with. I became a target of the national government virtually overnight.”
Sidney H. Davidoff — he insisted that the middle initial did not stand for anything — was born on July 18, 1939, in Brooklyn to Joseph and Belle (Klein) Davidoff. He grew up in Middle Village, Queens.
After graduating from Jamaica High School, he earned a bachelor’s degree in political science from City College in 1960 and a law degree from New York University in 1963. He met Mr. Lindsay when, as a young congressman, Mr. Lindsay spoke at N.Y.U.
“I knew he was going somewhere,” Mr. Davidoff told The New York Times in 1967.
After Mr. Lindsay was elected, Mr. Davidoff’s first job with the city was as an assistant buildings commissioner.
“I came into my office,” he recalled, “and a civil servant said, ‘Can I help you, sonny?’ ‘Yes,’ I said, ‘you’re sitting at my desk.’”
When reporters questioned his credentials for that job, which usually went to someone with technical or engineering expertise, Mr. Davidoff was unfazed.
“I’ve lived in buildings all my life,” he said.
In 1972, after he left city government, Mr. Davidoff and Mr. Aurelio, the former deputy mayor, opened a restaurant and nightclub, Jimmy’s, on West 52nd Street. It became a hangout for administration officials before closing in 1975.
The following year, Mr. Davidoff was indicted by a state grand jury on a charge of failing to file withholding taxes for his restaurant employees. A few months later, he agreed to pay a fine and back taxes, and the charge was dismissed.
In his MSNBC essay, Mr. Davidoff connected the indictment to his targeting by President Nixon and to Mayor Lindsay’s longstanding feud with Gov. Nelson A. Rockefeller of New York.
“For whatever reason, they couldn’t get to Lindsay, so they got to me,” Mr. Davidoff wrote. “The next best thing, I suppose.”
In 1975, he founded a law firm specializing in government relations; it eventually became Davidoff Hutcher & Citron.
By the administration of Mayor David N. Dinkins, in the early 1990s, the firm had become the city’s highest paid lobbyist, representing clients like the U.S. Tennis Association (Mr. Dinkins was Mr. Davidoff’s occasional tennis partner); Warner Cable (headed by Mr. Aurelio); the Trump Organization; and Vanguard Meter Services, a small Kentucky a company that was awarded a contract to install water meters in every city residence. (A grand jury later accused Vanguard of underpaying workers to gain a competitive advantage in the bidding.)
“It shouldn’t look like I’m being bought because I can lead them into City Hall,” Mr. Davidoff told The Times in 1990 — although, he added, “the fact is, I can.”
Mr. Dinkins was so angry about Mr. Davidoff’s boast that for a time he wanted to bar him from City Hall altogether.
Mr. Davidoff continued to practice law and advise clients until his death. He was a political consultant to the TV sitcom “Spin City” in the late 1990s and appeared as a divorce lawyer on an episode of “The Sopranos” in 2004.
His marriages to Patricia Miller and Bonnie Mandina ended in divorce. In addition to his wife, Ms. Stasi — they were married at City Hall by Mayor Bill de Blasio in 2014 — he is survived by a stepdaughter, Jessica Rovello, and three grandsons.
Mr. Davidoff was never one for nostalgia. At one reunion of Lindsay administration alumni a few years ago, he looked over the crowd and declared with mock surprise, “Oh, my god, I thought all of you were dead.”
But he remained wistful about the reformist Lindsay crusade.
“It was a moment in time,” he told The Times in 2005, “when people still believed they could make a difference.”
Sam Roberts is an obituaries reporter for The Times, writing mini-biographies about the lives of remarkable people.
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