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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Berkshire Law Enforcement Officials Endorse Fenton for Governor's Council

By Brittany PolitoiBerkshires Staff

Michael Fenton, a Springfield attorney, ran unsuccessfully for the 8th District seat on the council in 2022. He is challenging incumbent Tara Jacobs of North Adams. 
PITTSFIELD, Mass. — Ranking Berkshire law enforcement officials are putting their weight behind a Springfield lawyer for Governor's Council in the September Democratic primary over North Adams incumbent Tara Jacobs.
 
The Berkshires' District Attorney Timothy Shugrue, Sheriff Thomas Bowler, and Clerk of Courts Lisa Denault-Viale touted Michael Fenton's experience and approach over Jacobs, who bested him and two other attorneys in 2022.  
 
The Governor's Council advises the governor on matters relating to judicial appointments, treasury warrants, pardons and commutations, and a number of other important executive functions. The winner of the primary will represent the 8th District, which covers more than 100 cities and towns including North Adams, Adams, Pittsfield, Greenfield, Northampton and Springfield, as there is no other candidate on the November ballot.
 
Gathering at Park Square on Wednesday morning, Shugrue said Jacobs does not provide the representation Berkshire County requires and deserves. 
 
"This individual [Fenton] would conduct himself with a great deal of common sense and confidence," Bowler said. 
 
Fenton said there are only 11 Superior Court judges assigned to Western Mass, and that too few of them are from Berkshire County. 
 
"At one time there were four vacancies. That left only seven judges serving the entire 102 cities and towns of the western region. Seven judges serving 102 cities and towns at a time when you add Hampden County, Springfield, Holyoke, and Chicopee in, at a time when there were over 100 pending murder cases. Seven judges for 100 pending murder cases," he said. 
 
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