Tammany Hall: DeSapio, Giuliani & The Donald

From the time I first laid eyes on the great Tammany Hall Leader as a little boy, Carmine DeSapio wore rose-colored glasses and seemed as old as Father Time. (He was forced to wear dark glasses because of a chronic eye disease.) We’d meet at a club in Greenwich Village for Easter or Thanksgiving dinner with DeSapio, Meade Esposito, the Democratic Leader, and all our families.

I last saw DeSapio in the late 1980s. He looked exactly the same — right down to the rose-colored glasses — as he flirted mercilessly with my new fiancé. I had just returned from living in Rome and smoked English Ovals. DeSapio begged a few off me and smoked them with true joy. When I heard he was sick some years later, I had given up smoking for good. New York had become an unfriendly place for smokers in those days.

Those two things would always be linked in my mind: The great old man’s passing from New York City politics and the City’s “new” intolerance. It signaled the end of an era that began with DeSapio, was carried on in spirit by Meade Esposito and my father, and was dead as a doornail by the time another Italo-American, Rudolph Giuliani, emerged on the scene.

Dad was a Marine Corp. officer in Korea when Rudy Giuliani was a kid, but despite their age differences, they had more in common than not. Like my father, Giuliani was a smart kid educated by the Jesuits. They both possessed natural legal and leadership skills.

Jimmy and Rudy faced off more than a few times in Federal Court in some of New York’s most highly publicized trials. As politically motivated indictments became the cause célèbre of the day, though, there was no love lost between the two men. As a former prosecutor, the new “atmosphere” that Giuliani brought to the office — as effective as it may have been — was offensive to Jimmy, who was old school through and through: The resources of the United States government were not intended to squash defendants at will.

We all gave Rudy a pass after 9/11. His spirited defense of our beloved City was embraced by all of us. By that time, the pendulum had swung for good. The mob was decimated, Tammany Hall was a quaint reminder of smoke filled back rooms, and Rudy Giuliani — along with a man known throughout the City as “The Donald” — who we severely underestimated as a buffoon — were taking us to a place we could not have remotely predicted when I gave Mr. DeSapio my last English Oval.

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