Pittsfield Man Pleads Guilty to Cocaine Trafficking Conspiracy

BOSTON - A Pittsfield man pleaded guilty yesterday in federal court in Springfield to conspiring to traffic large quantities of cocaine in Western Massachusetts.

Theodore Warren, a/k/a "Monty," 42, pleaded guilty to one count of conspiracy to distribute and possession with intent to distribute cocaine and four counts of distribution of and possession with intent to distribute cocaine. U.S. District Court Judge Mark G. Mastroianni scheduled sentencing for Oct. 20, 2026. In December 2024, Warren was charged with his co-conspirator Lavante Wiggins, the former Dean of Pittsfield High School.

According to the charging documents, Wiggins, the former Dean of Students at Pittsfield High School, allegedly operated a drug trafficking organization (DTO) that distributed large amounts of cocaine in and around the Pittsfield area. Warren was a trusted member of the DTO who served as a runner for Wiggins. According to the charging documents, in August 2024, Wiggins expressed concern that he was under investigation and that he would send Warren to complete drug sales and deliver cocaine on his behalf. It is alleged that one of Wiggins' customers amassed a debt of more than $34,000 for cocaine that Wiggins provided on credit. Warren and, allegedly, Wiggins went about collecting on that debt while continuing to supply large amounts of cocaine to the customer. Specifically, Wiggins allegedly directed Warren to distribute cocaine to the customer on four separate occasions between September and December 2024: approximately 91 grams of cocaine on Sept. 10, 2024; approximately 100 grams of cocaine on Oct. 14, 2024; 125 grams of cocaine on Oct. 31, 2024; and 150 grams of cocaine on Dec. 10, 2024.

The charges of conspiracy to distribute and possession with intent to distribute cocaine and distribution of cocaine provide for a sentence of up to 20 years in prison, up to a lifetime of supervised release and a fine of up to $2 million. Sentences are imposed by a federal district court judge based upon the U.S. Sentencing Guidelines and statutes which govern the determination of a sentence in a criminal case.

United States Attorney Leah B. Foley and Ted E. Docks, Special Agent in Charge of the Federal Bureau of Investigation, Boston Division made the announcement today. Valuable assistance was provided by the Holyoke, Springfield, Chicopee, West Springfield, Easthampton and Pittsfield Police Departments; Berkshire, Hampden and Franklin County Sherriff's Offices; Massachusetts State Police; and the Berkshire County District Attorney's Office. Assistant U.S. Attorney Neil L. Desroches, Chief of the Springfield Branch Unit, is prosecuting the case.

The details contained in the charging documents are allegations. The remaining defendant is presumed innocent unless and until proven guilty beyond a reasonable doubt in a court of law.