Though his family settled in Italian Harlem (108th Street), within the territory of Ciro Terranova and the Morellos, Costello involved himself in the Five Points Gang on the Lower East Side. He was eventually initiated into the Mafia but often worked independent criminal enterprises with non-Italian partners. He was jailed for a year after a concealed weapon conviction in 1915. Costello moved with gusto into bootlegging during Prohibition Days and coordinated bootlegging activities across the country. He cultivated contacts among elected government officials and bureacrats and could provide insurance that law enforcement would leave alone the enterprises he sponsored.

During an Atlantic City convention in spring 1929, he helped guide the post-Prohibition activities of the Mafia and the multi-ethnic Syndicate which would be founded in 1931. During the Castellamarese War, Costello was nominally serving Joe Masseria's New York organization. But he and the other more Americanized Mafiosi - Charlie Luciano, Vito Genovese, Joe Adonis and others - were setting their sights on the future.

He busied himself with gambling ventures in the 1930s, obtaining official government OKs to place slot machines everywhere in New York. That brought him into direct conflict with reform Mayor Fiorello LaGuardia, who, despite court protection of the slots, collected all the machines in 1934 and personally destroyed them with a sledge hammer.

When Charlie Luciano was jailed in 1936, Costello was named to head the main Manhattan crime Family and to guide the Mafia Commission that oversaw the work of the nationwide Syndicate. Friction began between Costello and Vito Genovese, who had also been a key figure in Luciano's organization. Conflict was avoided when Genovese fled to Italy to avoid prosecution in the U.S. In 1945, Genovese, who had returned to New York, was acquitted of murder charges. Luciano had been deported to Italy, and there was little, aside from the reputation of Costello's ruthless and rabidly loyal ally Albert Anastasia, to prevent a confrontation between Costello and Genovese.

It took another decade for matters to come to a head. During those years, Costello was targeted both by Genovese's forces and by government agencies. He was called to testify before the Kefauver Committee and generated some of the more interesting moments in the televised proceedings when he insisted that cameras focus on his hands rather than his face.

In 1957, Costello was shot in the head by a would-be assassin's bullet. The bullet, however, only grazed the mob boss. He bled a bit but survived. Anastasia was not so fortunate. He was murdered later in the year. Costello announced his retirement from active Mafia life and turned the Luciano Family over to his rival Genovese. In later years, when Costello was jailed for tax evasion and Genovese for narcotics, the two former friends met in Atlanta's penitentiary and reconciled. Costello returned to a private life in New York after his prison sentence and died in 1973.

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