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Pay up or get pistol-whipped: Peabody Gangster Disciple gets 51 months for shaking down ex-recruit and his girlfriend from prison cell

Sunday, May 3, 2026
3 min read
MDN Staff
Pay up or get pistol-whipped: Peabody Gangster Disciple gets 51 months for shaking down ex-recruit and his girlfriend from prison cell

Damien Willette, 31, ran a Gangster Disciples extortion racket from his Massachusetts state prison cell, threatening pistol-whippings against a former recruit's girlfriend when the money stopped

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PEABODY — A Gangster Disciple from Peabody who tried to shake down a former recruit and his girlfriend from inside a state prison cell will spend the next 51 months in a federal one.
Damien Willette, 31, was sentenced this week by U.S. District Court Judge Richard G. Stearns in federal court in Boston to four years and three months in prison, followed by three years of supervised release, for conspiring to extort two victims with threats of pistol-whippings and worse.
The arrangement, according to federal prosecutors, was simple — and dressed up in Gangster Disciples lingo. Willette had recruited Victim 2 into the gang. Victim 2 quickly thought better of it and tried to walk away. Willette wasn't having it.

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He told the recruit he could be "blessed out" — gang-speak for an honorable exit — but only if he kept providing "aid and assistance," another Gangster Disciples euphemism that translated roughly to: send money while I'm locked up, and pay my friends too.
When Victim 2 stopped paying, his romantic partner — Victim 1 in the case — picked up the tab to keep him safe. That worked for a while. Then, around March 2023, Willette and his alleged co-conspirators decided to escalate.
The threats spelled out in the indictment were not subtle. Willette warned that if the payments stopped, gang members on the outside would pistol-whip the victims. "It's going to be bad for you and everyone you know," he told them.
Willette was serving a Massachusetts state sentence from November 2020 to May 2024 when most of this was happening. He was indicted in March 2025 alongside William Walley and Michael O'Shea — both alleged co-conspirators incarcerated with him at the time. He pleaded guilty in September 2025 to conspiracy to make interstate communications with intent to extort and to making interstate communications with intent to extort.
O'Shea was sentenced in January to 51 months — the exact sentence Willette just received. The case against Walley is still pending.

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