His business was centered in Little Italy, Manhattan, where he ran large extortion operations and committed other crimes including robberies, loan-sharking, and murder.

[2] Suspected of at least 60 murders, he was not caught by authorities until 1910, when the Secret Service arrested him for running a large scale counterfeiting ring in the Catskills.

[7] Upon settling in New York City, Lupo opened a store at East 72nd Street in Manhattan with his cousin Saitta, but moved his business to Brooklyn after a disagreement.

[6] Lupo's father, Rocco, joined him in New York City in 1902 and together they opened a retail grocery store on 39th Street between 9th and 10th avenues.

The Annual Report of the Attorney General for 1922 mentioned Lupo's desire to return to Italy but also noted that his codefendant, Giuseppe Morello, had received a commutation after just eight years of imprisonment.

[14][15] Harding did, however, attach a condition to the commutation, requiring Lupo to remain "law-abiding" and "not connected with any unlawful undertaking during the period of the sentence".

[16] Sometime in the early 1930s, the leaders of the emerging National Crime Syndicate called Lupo in for a meeting and forced him to give up nearly all of his rackets, except for a small Italian lottery in Brooklyn.

In 1936, New York Governor Herbert Lehman petitioned President Franklin D. Roosevelt to have Lupo returned to prison for massive racketeering.

[3] Lupo and the four Morello-Terranova brothers are interred in Calvary Cemetery in Queens, New York, not far from Joe Petrosino, who investigated them, and other Morello crime family members.