Carmine DeSapio

DeSapio always seemed a personally modest man. Even though he operated out of four lavish offices, he lived for fifty years in a middle-class apartment on Washington Square with his wife Theresa Natale ("Natalie") and daughter Geraldine. As leader of Tammany Hall, DeSapio reveled in the limelight, attending charitable fund-raising events, making himself available to the press, and delivering speeches in highbrow venues that were thought off-limits to political bosses. In wielding his enormous political clout, he usually preferred extensive consultations and consensus-building to unilateral decision-making. His 16- to-18-hour workday began with pre-breakfast phone calls at home where, still dressed in pajamas and bathrobe, he received a stream of political associates. DeSapio would then visit his various offices for further meetings, and cram in a half-dozen public functions, including radio and television appearances and a late-night political dinner.[3]

DeSapio succeeded in shucking Tammany's notoriety and fashioning himself as a sophisticated, enlightened and modern political boss. He favored well-tailored dark suits and striped ties and always looked as if he had just stepped out of a barber's chair. The only incongruity was the dark glasses he was forced to always wear because of chronic iritis.[3]

Throughout his political life, DeSapio was noted for alleged involvement with organized crime, even though he fought to distance the organization from the unsavory days of Boss Tweed,[3] and allegations of corruption. In 1951, Senator Estes Kefauver of Tennessee concluded that DeSapio was assisting the activities of New York's most powerful mobster Frank Costello, and that Costello had become influential in decisions made by the Tammany Hall council. DeSapio admitted to having met Costello several times, but insisted that "politics was never discussed".[3] These connections were examined by the Kefauver Commission.

However, it later became apparent that he was also selling out to benefit local mobsters such as Costello. DeSapio was accused of staffing New York City's government with clubhouse hacks. He followed the Tammany custom of selling judicial nominations, although he did cut the fee that would-be judges were required to pay.[3] He steered valuable city contracts for streetlights and parking meters to the Broadway Maintenance Corporation, a company that, according to the State Investigation Commission, cheated taxpayers out of millions of dollars.[3]

In 1953, he earned new respect and public admiration when he turned against the other Democratic leaders in New York City and used the power of Tammany Hall to help ensure that the highly-unpopular incumbent mayor, Vincent R. Impellitteri,[3] was defeated in the Democratic Party primary by Robert F. Wagner, Jr., an outspoken pro-reform Democrat,[5] and then helped assure Wagner's victory in the general election. Following Wagner's success, DeSapio became a powerful and well-respected kingmaker in the New York political scene.[3]

In 1958, DeSapio's image was severely damaged after he successfully manoeuvred to have his own candidate for Senate, Manhattan District Attorney Frank Hogan, placed on the Democratic and Liberal ticket.[3] New Yorkers now saw DeSapio as an old-time Tammany Hall boss and Hogan lost the Senate election to Republican Kenneth Keating. Republican Nelson Rockefeller was elected Governor the same year as well. Democrats who had once praised DeSapio now found it expedient to excoriate him. In 1961, Wagner won re-election by running a reformist campaign that denounced his former patron, DeSapio, as an undemocratic practitioner of Tammany machine politics.[3] The same year, DeSapio lost the district leadership of his native Greenwich Village, a post he had held for two decades, to an upstart reform Democrat, James Lanigan, who was backed by nationally known liberal Democrats such as Wagner, Eleanor Roosevelt and former Senator Herbert H. Lehman.[3]

His leadership ended in 1961, and with it the dynasty that was Tammany Hall. It took several years of work by Eleanor Roosevelt to bring this about. She told local journalist Murray Kempton, who published her remarks many years later in 1991 when he was a columnist for Newsday, "I told Carmine I would get him for what he did to Franklin, and get him I did."[3] She had vowed revenge because she felt DeSapio had derailed her son's (Franklin D. Roosevelt, Jr.) political ambitions by persuading him to abandon his run for Governor of New York in 1954 and instead run for New York Attorney General. After Roosevelt dropped out, DeSapio then got the local Democratic Party officials to accept former banker and diplomat W. Averell Harriman as the Democratic Party's nominee for governor in the New York state election. Harriman barely managed to secure victory as Governor of New York and Roosevelt would lose his bid to become the New York Attorney General. Following Harriman's victory, DeSapio served in Harriman's cabinet as Secretary of State of New York.[3]