New York City has recently elected (by a landslide) a liberal Democratic mayor named Bill de Blasio – and two weeks ago, Gotham (like the rest of the country) observed the 50th anniversary of the assassination of President John F. Kennedy. Another New York City politician, perhaps forgotten by many Americans, shared some characteristics with both de Blasio and Kennedy.

Like de Blasio, John V. Lindsay, the mayor of New York from 1965 to 1973, was tall, personable and wildly popular with a broad swath of the public; like Kennedy, Lindsay was an extremely handsome blue-blooded aristocrat who eventually supported the causes of people of far lower social rank.

Lindsay emerged on the national scene in the mid-1960s, as New York City found itself in the vortex of myriad urban ills – racial strife, labor unions in turmoil, economic malaise, soaring rates of drug abuse and violent crime and a collapsing manufacturing base. Of course, Lindsay’s tenure in Gracie Mansion also coincided with events in a country that was itself engulfed in a number of historic and troubling issues, including the Vietnam War, the civil rights movement, urban discontent and campus unrest.

Lindsay’s two terms as New York’s mayor were marked by some successes and some spectacular failures, leading to an unsuccessful presidential bid in 1972.

Lindsay died in 2000 at the age of 79.

International Business Times spoke to an expert on political affairs to assess Lindsay’s term in office and his legacy.

Vincent Cannato is the author of “The Ungovernable City: John Lindsay and His Struggle to Save New York” and professor of history at the University of Massachusetts in Boston.

IB TIMES: When John Lindsay was elected mayor of New York in 1965, who formed the base of his support? Blacks? Hispanics? White liberals? Jews?

CANNATO: John Lindsay’s base of support was not quite the liberal base that would re-elect him in 1969. Lindsay ran as a typical "anti-machine" Republican-Fusion reformer, not as a liberal. His base was basically Manhattan Republicans, business types and middle-class whites in the outer boroughs.

He got about 40 percent of the black vote and 25 percent of the Puerto Rican vote, which was good for a Republican, but not a majority. He also got 40 percent of the Jewish vote and did well among middle- and upper-middle-class Jews. He didn't win a majority of any of those voters, but did well enough among them to win the election.

It would be very different in 1969, when he would be a much more liberal candidate.

IB TIMES: Did the white working classes of Queens and Brooklyn comprise the principal anti-Lindsay contingent?

CANNATO: Not immediately, although the 1966 fight over the civilian complaint review board that would monitor charges of police brutality turned off many working-class whites. Lindsay actually did well in these neighborhoods in 1965, but as soon as he was elected he basically ignored them, and they would quickly turn against him.

IB TIMES: Bill di Blasio spoke of New York City being "two cities" (one rich, one poor). In Lindsay’s day, was the city more divided along racial lines, or was it more of a case of class divisions?

CANNATO: Hard to say. The concept of income inequality is a slippery one. I would probably say that New York City in the 1960s was much more divided along racial lines. There was certainly income inequality then, though. Middle-class whites had moved out of the city in droves in the 1950s and 1960s, largely replaced by lower-income minorities. But the greater division was that between white and black (and Puerto Rican to a lesser extent).

IB TIMES: In the late 1960s and early 1970s, New York City was hit with a number of crippling labor strikes. Did the unions generally support Lindsay, or were they adversaries?

LINDSAY: That's complicated. Lindsay was originally anti-union. He was a Republican reformer after all and saw unions as the "power-brokers" who were running the city and needed to be tamed. In his first term, he had problems with the transit workers union, teachers union and sanitation workers union. However, in 1969 he needed union support (or at least needed them not to be against him). Basically, he gave many public sector unions good contracts and that would win them over or at least neutralize their opposition in the 1969 campaign. He also forged a strong relationship with labor leader Victor Gotbaum, who helped him win over the unions.

IB TIMES: Did white flight accelerate during Lindsay's mayoral terms?

CANNATO: White flight began back in the 1950s when New York City lost about 1 million white residents. It continued into the 1960s and 1970s, when New York City lost more population. It certainly continued during the Lindsay years and continued to worsen after the fiscal crisis of the mid- and late 1970s.

IB TIMES: How did Lindsay prevent race riots from breaking out in New York City following the death of Martin Luther King in 1968?

CANNATO: It's a myth that Lindsay "prevented" race riots from breaking out after King's murder. New York City certainly did not see the same kind of rioting as Washington, D.C., and other cities, but it did see a not insignificant amount of rioting in Harlem and Brooklyn that night. The administration minimized the damage. Lindsay did show up at Harlem that night and defused some of the tensions. Whether or not it stopped the rioting, it was a brave and symbolic gesture on his part.

IB TIMES: Did crime surge during Lindsay's terms in office? If so, was he blamed for it?

CANNATO: Crime began increasing under the administration of Lindsay’s predecessor Mayor Robert Wagner (1954-1965), but really increased under Lindsay. That was one of the things that hurt Lindsay and created lots of opposition to him. He had no answers in dealing with the crime problem.

IB TIMES: How did Lindsay get along with the NYPD during those years?

CANNATO: Lindsay had a difficult relationship with the NYPD, especially after the civilian complaint review board campaign of 1966. There was also the shooting at a Harlem mosque in the early 1970s that was covered up.

However, as with other unions, Lindsay did give generous contracts to the police and that muted some of that opposition by the second term.

IB TIMES: Is it true that Lindsay was anti-Semitic?

CANNATO: No, Lindsay was not anti-Semitic. Many of his aides were Jewish. However, he was not hugely comfortable around ethnic Jews (as opposed to more assimilated and professional Jews). His biggest problems were with middle- and working-class Jews who believed that Lindsay did not care about their concerns.

IB TIMES: When conservative mayoral candidate Mario Procaccino coined the term "limousine liberal," was he speaking specifically about Lindsay?

CANNATO: Yes, he was referring to Lindsay and Lindsay's wealthy supporters.

IB TIMES: Much was made about Bill de Blasio’s height (6-foot-5) during the recent mayoral campaign. Lindsay was also very tall -- was his height an advantage back in the 1960s?

CANNATO: It was not just that he was tall, but he was good looking and athletic (which de Blasio is not) that helped him. Women swooned over Lindsay and you still hear from women today who remark about how attractive Lindsay was.

IB TIMES: How did Lindsay’s movie star-handsome looks impact his campaigns and political career? Did they help or did they make him seem like a lightweight?

CANNATO: Probably both. Being attractive certainly helped him with his career, but it was a double-edged sword and could sometimes be used against him by critics who called him a lightweight.

IB TIMES: What were Lindsay's biggest accomplishments during his mayoralty?

CANNATO: His administration was largely an honest one with little corruption. He hired good people who would later go on to have distinguished careers in city government and private business. He was sensitive to the city's minority communities and worked to increase their access to city government services.

IB TIMES: What were Lindsay's biggest failures?

LINDSAY: There were many. His biggest one was his failure to rein in spending during his second term when the city’s economy seriously deteriorated. There was little understanding of the larger economic shifts going on and how many jobs the city was losing. The city kept spending, did not try to attract new businesses or keep old ones, and had to go back to old budget gimmicks and borrowing, which led to the fiscal crisis of 1975.

He also failed to do anything about rising crime. His policies and attitudes helped polarize the city and alienate large swaths of outer-borough working-class whites who believed that he didn't care about their problems. He presided over a city that was quickly deteriorating and he had few answers to those problems.

IB TIMES: Lindsay was a Republican until 1971 -- why did he switch to the Democrats?

CANNATO: Lindsay lost the Republican primary in 1969 to [New York State Senator from Staten Island] John Marchi and had to win re-election as an Independent/Liberal. Lindsay was growing more liberal and the Republicans were becoming more conservative. The Democratic Party was a much more natural fit for Lindsay by 1971.

IB TIMES: Why did Lindsay's 1972 presidential bid fail?

CANNATO: Lindsay's presidential bid failed because he had only been a Democrat for one year and did not have a lot of support within the party. The city was also in bad shape in 1972, so he was dogged by lots of problems in the city and had a hard time pointing to any accomplishments in the city. It was also a poorly run campaign which he should have never taken on.

IB TIMES: What do you think is Lindsay's legacy in New York City?

CANNATO: Lindsay is in many ways a tragic figure, one who began his mayoralty with great energy and idealism. He promised many things, but when he left office eight years later the city was much worse off. He was a good man who tried to do well, but was unable to successfully grapple with the problems of the city during this turbulent era and in some ways made things worse with his policies.