This week’s History Thread remembers John Vliet Lindsay, who was elected Mayor of New York City in 1965. A handsome Ivy League WASP and former Congressman, Lindsay was the last of a dying breed – a genuinely liberal Republican who sought to overcome the city’s corruption, racial strife and ineffectual government through good works, progressive politics and charisma. His election was greeted with widespread excitement: “he is fresh,” Murray Kempton famously wrote, “and everyone else is tired.” Lindsay easily bested Democrat Abraham Beame and third party candidate William F. Buckley; the Mayor-elect proclaimed New York “Fun City,” and the media initially swooned, some immediately deeming him presidential timber.

The honeymoon didn’t last a day: Lindsay’s term began with a citywide transit strike, an appropriate curtain raiser on a tumultuous administration. The Mayor of “Fun City,” it seemed, couldn’t handle the city’s worsening problems. His administration fought battles over school desegregation, the Vietnam War, police corruption, the city budget and a skyrocketing crime rate which combined to deaden New Yorkers’ enthusiasm. Lindsay alienated white New Yorkers by embracing youth protest movements (he even hired Abbie Hoffman as a community liaison), addressing antiwar rallies and, most of all, making regular visits to Black and Puerto Rican communities. One landlord complained that “Lindsay will see the hippies, but he won’t see the taxpayers.”

Of course, those minorities had a different perspective. Lindsay regularly visited minority neighborhoods like Harlem and Bedford-Stuyvesant to build a rapport with Black and Puerto Rican voters, chatting with residents, playing in fountains with children and helping to broker truces between local street gangs. Decades later, the Reverend Al Sharpton recalled the awe Lindsay inspired as “a tall, lanky guy who had all the power, and he came to our community.” Even the gangs treated the Mayor with a respect they rarely accorded politicians, especially white ones. When H. Rap Brown turned up in Harlem preaching the need for revolution, a local drug dealer confronted him: “If you ever come back here talking that sort of shit, we’ll kill you.”

Nor was Lindsay all talk. The night of Martin Luther King’s assassination, the Mayor (who had been attending a Broadway show) walked to Harlem to cool racial tensions with a small entourage of aides. When an aide told Lindsay it was a bad idea, he responded that “somebody white just has to face that emotion and say that we’re sorry.” The Mayor followed through, addressing a Black crowd along 125th Street and leading them in a peaceful march through the neighborhood. When one of the Mayor’s aides expressed fear of violence, a local teen named Bobby stepped in. “Don’t worry,” he assured the Mayor. “Nobody can get to you while Bobby’s here.” Assisted by Bobby and hundreds of other sympathetic locals, Lindsay helped New York avert the major bloodshed that swept across other cities.

Such events enhanced Lindsay’s standing with liberals, and he assiduously courted the media. Lindsay guest hosted the Today Show, socialized with Robert Redford (who partially based his performance in The Candidate on Lindsay), and even had a fling with Brady Bunch mom Florence Henderson. He co-chaired the Kerner Commission, convened by President Johnson to investigate the recent outbreak of race riots, and likely authored its famous conclusion that America was moving towards “two societies, one black, one white, separate and unequal.” Richard Nixon seriously considered Lindsay as a running mate in 1968, until Southern conservatives made clear that they wouldn’t ever accept the Silk Stocking Mayor on the ticket.

But it often seemed that Lindsay’s reputation shone brighter outside the city than within. His administration constantly stumbled in its fights with city power brokers. His Police Review Board faltered from bureaucratic snarls and concerted resistance from cops and conservatives, who complained that “communists are mixed up in this fight”; their leader admitted that he was “sick and tired of giving in to minority groups.” His support for desegregation and “community control” over schools led to a vicious teacher’s strike in Ocean Hill-Brownsville, where Black community leaders and largely Jewish teachers battled over control over the local school district. One teacher was so infuriated by Lindsay’s handling of the strike that he vowed that “I’ll do just what Oswald did to John Kennedy.”

It didn’t help that Lindsay’s staff had a tendency to put their foot in their mouth, responding even to reasonable criticism with dismissive condescension. One Lindsay aide, when asked about the NYPD’s resistance to police reform, responded that he wasn’t surprised because “all cops are scum.” August Heckscher II, the philanthropist who served Lindsay’s Parks Commissioner, once responded to complaints about muggings and other violence in Central Park by mocking citizens as “scared of the abundance of life.” No wonder one of Lindsay’s political opponents branded the Mayor a “limousine liberal,” a headline-grabbing swell eager to pass judgment on his constituents from the comfort of Gracie Mansion.

After Lindsay’s narrow reelection he left the Republican Party, governing as an independent as New York gained a reputation as a wretched hive of scum and villainy – “a cut-rate Fellini Satyricon” in the words of one editorial writer, overrun with crime, drugs and general discontent. Lindsay switched to the Democratic Party for a quixotic Presidential bid in 1972 (“He can’t run New York and now he wants to run the country,” scoffed a Florida Democrat), then resigned the Mayorship the following year. Adding insult to injury, fallout from his financial policies played a major role in the city’s economic collapse of 1975, leaving his successor Abe Beame to clean up the mess. Although Lindsay wrote novels, appeared in films and occasionally tried to run for office again, by his death in December 2000 he’d been diminished to an historical footnote.

Historians have typically dismissed Lindsa,y as one of the worst mayors of the 20th Century, a reputation not unearned if overly harsh considering the obstacles he faced. (The only full-length biography of Lindsay, Vincent Cannato’s The Ungovernable City, treats his administration as an abject failure.) Yet Lindsay retains his admirers: his charisma and good works inspired a generation of young political activists to enter politics; his sympathies for New York’s poor and minorities have earned him widespread admiration. Even the cynical Hunter S. Thompson admitted to respecting Lindsay, who far all his faults “seemed open to almost any kind of idea” and showed genuine empathy for the downtrodden. At the very least, his Mayorship serves as a cautionary tale about the limits that even well-intentioned reformers face when running a big city.