BOSTON — On Tuesday, June 23, 2026, a Newtonville man was sentenced in federal court in Boston to five years in prison for cocaine distribution, according to the U.S. Attorney’s Office for the District of Massachusetts.
Trevor Headley, 32, was sentenced by U.S. District Court Judge Allison Burroughs to five years in prison, followed by four years of supervised release.
In April 2026, Headley pleaded guilty to one count of possession with intent to distribute 500 grams or more of cocaine and two counts of distribution of and possession with intent to distribute cocaine. Headley was arrested and charged in October 2025.
According to federal prosecutors, Headley sold cocaine to an undercover law enforcement officer on multiple occasions in August 2025. Prosecutors said Headley arranged the first transaction through a series of communications before meeting the undercover officer at a pre-arranged location on Aug. 12, 2025, and selling approximately 112 grams of cocaine. On Aug. 27, 2025, Headley conducted a second controlled transaction, selling approximately 451 grams of cocaine.
During recorded phone calls with the undercover officer in September 2025, Headley discussed obtaining an additional kilogram of cocaine for sale and expressed interest in obtaining firearms and machine gun conversion devices, stating that the firearms would be included as part of the negotiation in exchange for cocaine, the U.S. Attorney’s Office for the District of Massachusetts reported.
During a search of Headley’s residence after his arrest in October 2025, authorities recovered approximately three kilograms of cocaine packaged for distribution, more than $32,000 in cash, and other items consistent with drug trafficking.
Federal prosecutors described Headley as a known associate of the Charlestown Bloods street gang.
United States Attorney Leah B. Foley; Thomas Greco, Special Agent in Charge of the Bureau of Alcohol, Tobacco, Firearms and Explosives, Boston Field Division; Jarod A. Forget, Special Agent in Charge of the Drug Enforcement Administration in New England; and Boston Police Commissioner Michael Cox announced the sentence.
Assistant U.S. Attorney John T. Dawley of the Organized Crime & Gang Unit prosecuted the case.
The case is part of Operation Take Back America, a nationwide Department of Justice initiative that incorporates resources from the Organized Crime Drug Enforcement Task Forces and Project Safe Neighborhoods.
