Pittsfield Police Capt. Wynn Goes From Bars to Stars

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Acting Chief Michael Wynn waves at last year's Pittsfield Fourth of July Parade.
PITTSFIELD, Mass. — The city's ranking police officer was named acting police chief today but the announcement merely reaffirms what he's been doing right along.

Michael Wynn, 38, has been leading the force for a year with the title "captain in charge."

"For the past 13 months, Chief Wynn has been a great asset and face to the Pittsfield Police Department," said Mayor James M. Ruberto, who made the appointment. "And I will continue to show my support of Chief Wynn every day."

The Pittsfield native stepped in to replace Police Chief Anthony Riello, who took a position with the Falmouth Police Department. Ruberto has named him acting chief to sidestep Civil Service requirements. The city placed the positions of police chief and fire chief back on the Civil Service rolls in 1991, which would require Ruberto to chose from the top three candidates applying for the job.

The mayor has said he's happy with both Wynn and acting Fire Chief James C. Sullivan, a deputy chief who replaced another acting chief, Stephen Duffy, who retired in 2006.


Wynn has been with the force for 13 years in various positions, rising from patrol officer to supervisor, and has trained with the U.S. Drug Enforcement Agency and the Marin Corps.

Last month, he was signing copies of his book "Rising Through the Ranks: Leadership Tools and Techniques for Law Enforcement" at Chapters Bookstore on North Street.

"I totally support the mayor's decision to appoint Captain Wynn to acting chief," said City Council President Gerald Lee. "Captain Wynn has done an outstanding job and is well deserving of the appointment."

Wynn graduated from Taconic High School in 1988 and earned his bachelor's degree from Williams College and his master's degree in criminal justice from Anna Maria College in Paxton. He has been married seven years and has two stepchildren and two stepgrandchildren.
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Pittsfield Remembers Lives Lost to Overdose, Underscores Harm Reduction

By Brittany PolitoiBerkshires Staff

Mayor Peter Marchetti reads a proclamation at City Hall encouraging residents to raise awareness and lift each other up. 

PITTSFIELD, Mass. — Dozens of people gathered downtown on Monday to remember those lost to overdose and work toward a future of zero deaths from substance use disorder. 

The Berkshire Overdose and Addiction Prevention Collaborative and its partners held a proclamation reading and flag-raising at City Hall, followed by a standout in Park Square with signs promoting the use of naloxone, harm reduction, and reducing associated stigma. 

There were 23 fatal overdoses in Berkshire County in 2025, 11 in Pittsfield. This is down 44 percent from the 41 countywide fatalities in 2024. 

While it is a significant decrease, advocates want to see that number at zero. 

"On the one hand, we're very pleased to see this significant of a decrease. This is actually the lowest number that we've had since [Department of Public Health] started collecting these numbers in 2013, but the goal is still zero," said Andy Ottoson, public health planner with the Berkshire Regional Planning Commission. 

August is International Overdose Awareness Month, the world's largest annual campaign to end overdose, remember those lost without stigma, and acknowledge the grief of families and friends left behind. September is National Recovery Month, a national observance to educate the public on the importance of substance use treatment and mental health services.

Samantha Kendall of Berkshire Harm Reduction explained that it is truly meeting people where they are, as they are, and when they are, "and I think we all do a really great job at that."

"We also want to remember that we're building a community for everybody, and systems and policies for everybody. That's really important in harm reduction work, so that's also the reason we're here today," she said. 

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