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 ConCom OKs Wahconah Park Demo, Ice Rink

By Brittany PolitoiBerkshires Staff

PITTSFIELD, Mass. — The Conservation Commission has OKed the demolition of Wahconah Park and and the installation of a temporary ice rink on the property. 

The property at 105 Wahconah St. has drawn attention for several years after the grandstand was deemed unsafe in 2022. Planners have determined that starting from square one is the best option, and the park's front lawn is seen as a great place to site the new pop-up ice skating rink while baseball is paused. 

"From a higher level, the project's really two phases, and our goal is that phase one is this demolition phase, and we have a few goals that we want to meet as part of this step, and then the second step is to rehabilitate the park and to build new a new grandstand," James Scalise of SK Design explained on behalf of the city. 

"But we'd like these two phases to happen in series one immediately after the other." 

On Thursday, the ConCom issued orders of conditions for both city projects. 

Mayor Peter Marchetti received a final report from the Wahconah Park Restoration Committee last year recommending a $28.4 million rebuild of the grandstand and parking lot. In July, the Parks Commission voted to demolish the historic, crumbling grandstand and have the project team consider how to retain the electrical elements so that baseball can continue to be played. 

Last year, there was $18 million committed between grant funding and capital borrowing. 

This application approved only the demolition of the more than 100-year-old structure. Scalise explained that it establishes the reuse of the approved flood storage and storage created by the demolition, corrects the elevation benchmark, and corrects the wetland boundary. 

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