According to the United States Attorney’s Office for the District of Massachusetts, a Newtonville man was sentenced to five years in prison for cocaine distribution on Tuesday, June 23, 2026, in federal court in Boston.
U.S. District Court Judge Allison Burroughs sentenced Trevor Headley, 32, to five years in prison followed by four years on supervised release.
Headley pleaded guilty in April 2026 to one count of possession with intent to distribute 500 grams or more of cocaine, as well as two charges of distribution and possession with intent to distribute cocaine. Headley was arrested and charged in October 2025.
According to US prosecutors, Headley sold cocaine to an undercover law enforcement officer many times in August 2025. Prosecutors claim Headley orchestrated the first transaction through a series of contacts before meeting the undercover officer at a prearranged location on August 12, 2025, and selling roughly 112 grams of cocaine. On August 27, 2025, Headley carried out a second controlled transaction, selling roughly 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 an interest in obtaining firearms and machine gun conversion devices, stating that the firearms would be included in the negotiation in exchange for cocaine, according to the U.S. Attorney’s Office for the District of Massachusetts.
During a search of Headley’s home after his arrest in October 2025, authorities discovered nearly three kilograms of cocaine prepared for distribution, moreover, $32,000 in cash, and other drug-related things.
According to federal prosecutors, Headley is a known member of the Charlestown Bloods street gang.
The sentence was announced by 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.
The case was prosecuted by Assistant US Attorney John T. Dawley of the Organised Crime and Gang Unit.
The case is part of Operation Take Back America, a national Department of Justice initiative that includes resources from the Organised Crime Drug Enforcement Task Forces and Project Safe Neighbourhoods.
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