Joseph Cutaia, a 47-year-old associate of the Lucchese crime family and grandson of the late capo Domenico Cutaia, has pleaded guilty to federal extortion charges stemming from a series of threats and demands for money against two businessmen. The incidents occurred before and after his release from prison in late 2023, court documents reveal.

Cutaia, who was incarcerated on a home invasion robbery conviction and had served approximately 15 years, resumed criminal activity shortly before his release. According to prosecutors, he began extorting one of the victims, identified in filings as “John Doe #1,” while still in federal custody. He contacted the businessman and directed payments to his wife, eventually extracting about $50,000 over several months. To reinforce his reputation, Cutaia sent the victim a screenshot of his profile from an online “Mob Facts” website, which detailed his ties to the Lucchese family and described him as a “future force to be reckoned with.”

During exchanges, Cutaia issued threats, warning the victim he would not tolerate disrespect and demanding $10,000 to end the harassment. At one point, after Cutaia was arrested for reckless driving in Indiana, he had his wife contact the victim to request additional funds on his behalf.

The second victim, “John Doe #2,” co-owned a merchant cash advance business. In April 2024, Cutaia reportedly appeared at the victim’s place of business armed, threatening violence and claiming he was owed $100,000. He demanded that both the victim and a companion surrender their luxury watches, specifically a Rolex Daytona and a Patek Philippe Nautilus. Following his arrest in June 2024, prosecutors said Cutaia asked his wife to dispose of the Rolex and to disable his cellphone.

In recorded jailhouse conversations, Cutaia compared himself to notorious Depression-era gangster John Dillinger, boasting about future returns from prison and expressing defiance. “I do eight years and then I’m home. Then I come out like John Dillinger. Ain’t nothing stopping me,” he stated.

Prosecutors are seeking a prison sentence of approximately five to six and a half years, to be followed by an additional two years linked to the violation of his supervised release related to the earlier robbery case. Cutaia’s sentencing is scheduled for Tuesday in Brooklyn Federal Court, with a separate hearing on June 26 addressing the supervised release violation.

Defense attorney Gary Cutler noted in court documents that despite Cutaia’s guilty plea, he considered the first victim a friend and the second victim a close friend’s brother. Cutler also highlighted that Cutaia was recognized by the Brooklyn Metropolitan Detention Center warden for preventing a fellow inmate’s suicide attempt.