There are many former New Yorkers in Westport today who remember New York City Mayor John V. Lindsay's dream of transforming that once-failing metropolis in the 1960s into an example of first-class urban living. Following, Westport News columnist Woody Klein, Lindsay's first press secretary in 1966, tells a first-hand account of the outset at the mayor's inauguration 50 years ago.

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I had an epiphany exactly 50 years ago on Jan. 1, 1966, in New York City that turned into a nightmare before my eyes.

My highest hopes for the city I had covered as an investigative reporter in the 1950s and 1960s were raised to a dizzying height when the debonair, 43-year-old, 6-foot, 4-inch, 185-pound Republican-Liberal candidate, John V. Lindsay was elected in 1965 as the 103rd mayor of New York City. He ran to sweep aside the tired old smoke-filled, back-room clubhouse hacks.

On Dec. 31, 1965, New Year's Eve, the new mayor, brimming with certitude, was caught in an epic struggle to avoid a citywide transit strike. He bargained non-stop all night in a deadlocked session — perhaps naively in hindsight — to shape a by-the-book collective bargaining agreement with the fiery, 60-year-old Irish union chief Michael J. Quill of the Transport Workers Union. I was there, watching every motion and listening to every sharp word as the two men exchanged verbal punches in a large, secluded room in the basement of the Americana Hotel in New York.

Quill's voice bellowed during his vitriolic attack. Lindsay's face turned grim. Watching the mayor intently and sitting directly opposite him were the three-member arbitration panel, which was attempting to find a solution to the deadlock between the City of New York and the 33,000-member Transport Workers Union. On the mayor's right sat his shrewd, 33-year-old, deputy mayor, Robert Price. I sat on Lindsay's left taking notes, once whispering to him a few words of advice: "Keep your cool." He nodded, but he could hardly contain himself.

As the midnight deadline to make a deal passed, Lindsay appealed to the public interest and charged that Quill had "waited until the eleventh hour." Quill, furious, responded by storming out of the meeting, taking members of the Transport Union Workers and the Amalgamated Transit Union with him, purposely mispronouncing the mayor's name: "Mayor Lindsley. You are nothing but a juvenile, a lightweight and a pipsqueak. You have to grow up. You don't know anything about the working class. You don't know anything about labor unions," he shouted. Lindsay rose and replied deliberately: "I don't mind your words about me personally. You are entitled to your own opinion. But I will not have you addressing the office of the mayor that way. It is an affront to the people of the City of New York."

The headline on The New York Times front page on Tuesday, Jan. 2, 1966, said it all: “Subways and Buses Halted by Strike; Lindsey Appeals for a Curb on Travel; Inaugural Asks Fight for a Better City.”

I'll never forget the sinking feeling I had in the pit of my stomach when the transit workers walked out first thing in the morning on New Year’s Day, the first city-wide transit strike since 1916. It did not end until 12 days later, when Lindsay offered workers a generous wage and pension package. The settlement cost the city at least $43 million over two years, foreshadowing a host of expensive future contracts with other municipal workers.

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Lindsay had given up his safe seat as the upscale, Yale Law School congressman-politician who had represented the fashionable 17th "Silk Stocking" Congressional District on Manhattan's Upper East Side for eight years. Just a week before his election in November 1965, Lindsay stated: “New York City needs, and must have, a change. It must change completely in all of its institutions from top to bottom,” he said. People liked that attitude. Whenever he walked the streets, he was mobbed, people hounded him for his autograph, or to have a picture taken with him. He was, in effect, the "new John F. Kennedy" only two years after the martyred young president had been slain.

It was during those early days that I accompanied Lindsay on an overnight trip to Washington, D.C., to meet with some of his former congressional friends. We stayed overnight at the Hay-Adams Hotel in a room overlooking the White House. I recall saying, briefly, as I pointed to the White House lit up at night: "What do you think, John? Could we ever make to the White House?" Pure naiveté on my part. .

In this first inaugural address on Jan. 1, 1966, Lindsay threw down the gauntlet by introducing the phrase, "The Powerbrokers," his description of those forces whom he challenged in an effort to reform the generations-old way of New York politics. Within minutes of uttering the phrase, reporters rushed into my office and demanded to know exactly who Lindsay was talking about. "Hey, Klein, you better name names!" one old-timer reporter shouted. Previously, Lindsay had instructed me: "Tell them, 'They know who they are!' " That's as much as he or I ever said in answer to that question.

When I first entered the press secretary's office on the main floor of City Hall, I found a small blue-and-white-covered paperback on a handsome, red mahogany desk — a replica of the writing table George Washington used in the nation's first capital. The book was a copy of Niccolò di Bernardo dei Machiavelli's "The Prince." A piece of paper had been inserted in it which caught my eye. Underlined appropriately was the following passage: "There is nothing more difficult to take in hand, more precarious to conduct, or more uncertain in its success, than to take the lead in the introduction of a new order of things." Well stated, I thought.

I never did figure out how to win over the press during the municipal strikes, racial unrest, antiwar protests and other upheavals of the 1960s and early ’70s. The mayor, nevertheless, running as a Democrat in the 1969 mayoral primary on the Liberal-Fusion lines, emerged victorious in his re-election bid for a second term. But his try for the Democratic nomination for the U.S. presidency in 1972 far fell far short of the mark.

He is remembered today as a bright political spark that lit up the nation's hopes for a moment in time. But from his turbulent years as Republican-Liberal and Liberal-Fusion mayor from 1966 to 1973, and from his fading years as a Democrat who fell far short of a presidential nomination in 1972 and a Senate nomination in 1980, he never did reach the pinnacle of national politics.

Woody Klein, a Westport writer, has spent much of his 60-year career as a journalist either covering politics or serving in various government posts. He can be reached at His "Out of the Woods" column appears every other Friday in the Westport News. This article is based, in part, on Klein's 1970 book, "Lindsay's Promise."