[1] Tammany Hall had dominated New York City politics from the mayoral victory of Fernando Wood in 1854 until the election of Fiorello H. La Guardia in 1933.

DeSapio's Italian heritage signaled the end of Tammany's longtime dominance by Irish-American politicians, and he became the first nationally prominent Italian-American political leader.

[3] DeSapio reformed Tammany Hall's traditional sale of judgeships early in his role as Boss, reducing the cost of a position of a judge from $75,000 to $25,000.

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.

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] 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 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.

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] In 1963 and 1965, after Lanigan stepped down, DeSapio tried to retake his position as Greenwich Village district leader, but was twice defeated by another reform candidate, Edward I. Koch, who became mayor in 1977.

[3] DeSapio reached a low point in 1969 when he was convicted in a federal court of conspiracy and bribery after it was acknowledged that he conspired to bribe the New York City water commissioner, James L. Marcus, and extort contracts from Consolidated Edison that would result in kickbacks.