During the course of his counterfeiting investigation, Secret Service Agent William Flynn allowed DiPrimo's underworld associates to believe that he was providing evidence against them. Flynn did this in an effort to convince the other suspects to cooperate. The ploy was unsuccessful, and DiPrimo's perceived violation of the underworld code had an undesired effect. It led to the brutal Mafia slaying of his brother-in-law Benedetto Madonia (the "Barrel Murder").
Newspapers of the time, unaware of Flynn's manipulations, attributed Madonia's killing to a squabble over counterfeiting racket proceeds. In a series of articles published years later, Flynn fessed up to the divide-and-conquer effort that cast suspicion on DiPrimo and triggered the death of Madonia.
Morello enforcer Tomasso Petto was indicted for the Madonia murder. Of the suspects arrested, he was the only one still bearing incriminating evidence - a pawn ticket for DiPrimo's watch. Petto won release on bail and fled to northeastern Pennsylvania.
DiPrimo reportedly swore revenge against the Lupo-Morello organization for Madonia's death. It was widely believed that he tracked Petto to Pennsylvania and killed him there in October 1905. However, the timing was wrong for DiPrimo to be the killer, as he was still in prison at the moment Petto was shot to death.
DiPrimo might have supplied later evidence that resulted in the 1909 counterfeiting arrests of Lupo and Morello and much of their gang. Released from prison, DiPrimo fled back across the Atlantic. He reportedly was later gunned down in Italy.
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