Pittsfield Man Pleads Guilty to Cocaine Trafficking

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SPRINGFIELD, Mass. —  A Pittsfield man pleaded guilty on Monday in federal court for conspiring to traffic large quantities of cocaine in Western Massachusetts. 

Theodore Warren, also known as "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. 

This carries a sentence of up to 20 years in prison, up to a lifetime of supervised release, and a fine of up to $2 million. U.S. District Court Judge Mark G. Mastroianni scheduled sentencing for Oct. 20. 

In December 2024, Warren was charged with alleged co-conspirator Lavante Wiggins, a former dean at Pittsfield High School. Three administrators and two teachers, past and present, were investigated by Bulkley Richardson and Gelinas LLP for a range of allegations that surfaced or resurfaced at the end of 2024 after the arrest. 

This drew national media attention. 

According to the charging documents, Wiggins allegedly operated a drug-trafficking organization that distributed large amounts of cocaine in and around the Pittsfield area. Warren is said to have been a "runner."


"Warren was a trusted member of the DTO [drug-trafficking operation] 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," the U.S. Attorney's Office wrote in a press release on Tuesday. 

"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." 

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

U.S. Attorney Leah B. Foley and FBI Special Agent Ted E. Docks of the Boston Division made the announcement on Tuesday. 

Assistance was provided by the Holyoke, Springfield, Chicopee, West Springfield, Easthampton and Pittsfield Police Departments; Berkshire, Hampden and Franklin County Sheriff's Offices; 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 Berkshire Eagle reported in June that Wiggins appeared to be negotiating a plea in his federal cocaine distribution case. That same month, a Berkshire Superior Court judge approved a bank's request to seize Wiggins' 2023 Maserati after he allegedly missed 17 months of payments, leaving a balance of more than $86,000. The final payment that went through came days before his December arrest.


Tags: drug trafficking,   US Court,   

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Pittsfield Schools Finalizing Bus Routes for Fall

By Brittany PolitoiBerkshires Staff

PITTSFIELD, Mass. — The district currently has enough bus drivers for the upcoming school year, and families will know their child's transportation schedule in mid-August. 

With about five weeks left of summer vacation, Superintendent Latifah Phillips updated the School Committee on transportation for the 2026-2027 year with middle school restructuring and the closure of Morningside Community School. 

Busing is a question that has continuously been raised as the Pittsfield Public Schools approach an academic year with a couple of big changes. 

"The reason that the bus stops and times aren't shared until very close to the school year is that routes change based on every student that moves into the district and requires a bus, and so it's important for us to wait as late as possible to ensure that families are getting the most accurate timetable," Phillips explained during a meeting held at Reid Middle School on Thursday. 

"We are also continuing to explore after-school transportation for the four schools receiving Morningside, and a survey was given to students who attend the Summer Morningside 21st Century Program to assess transportation needs."

That survey found that transportation does not appear to be a big impediment to students participating in the after-school program, but funding is set aside to ensure students are able to access the same services as they were the previous year. 

The district is still planning to offer after-school programming for Morningside transfer students, and is working with the four receiving elementary schools (Allendale, Egremont, Williams, Capeless) to plan a practice bus ride. 

Phillips explained that, for someone who has never ridden a bus before, and especially a school bus, they want to ensure that students are poised for success and understand the rules and expectations before the first ride. Students will be able to get on the bus, ride the route, arrive at school, have a quick break, maybe play on the playground and have a popsicle, then return home on the bus. 

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