Pittsfield Police Capt. Wynn Goes From Bars to Stars

03:06PM / Thursday, January 22, 2009Print Story | Email Story

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.

iBerkshires.com Text Ads

rk MILES Blding Materials

Are You Ready to Update Your Home? Start With rk MILES. 4 Locations (800)670-7433

www.rkmiles.com

RIBCO Supply

Check out our great lineup of Boss Plows, and spreaders. 2 Locations Clarksburg & Pittsfield!

ribcosupply.com

If you would like to contribute information on this article, contact us at info@iberkshires.com.

Pittsfield ARPA Funds Have Year-End Expiration Date

By Brittany PolitoiBerkshires Staff
05:20AM / Thursday, January 15, 2026

PITTSFIELD, Mass. — American Rescue Fund Act monies must be spent by the end of the year, and Pittsfield is already close.

In 2021, the city was awarded a historic amount of money — $40,602,779 — in federal remediation funds for the COVID-19 pandemic. Through the end of September 2025, more than $37 million had been expended, and 90 percent of the 84 awarded projects were complete.

Special Project Manager Gina Armstrong updated the City Council on the ARPA funds during its first meeting of the new term on Tuesday.

As of September 2025, the $4.7 million allocated for public health and COVID-19 response has been fully expended. Additionally, $22.7 million of the $24.9 million allocated for negative economic impacts has been expended, and nearly all of the infrastructure funds, more than $5.8 million, have been expended.

Less than $3 million of the $3.7 million allocated for revenue replacement has been spent, along with about $873,00 of the $1.1 million allocated for administration.

Armstrong noted that in the last quarter, "Quite a bit more has been done in the areas of the housing projects." In 2022, then-Mayor Linda Tyer allocated $8.6 million in ARPA funds for affordable housing initiatives, and the community is eager for those additional units to come online.

Nine supportive units at the Zion Lutheran Church on First Street received more than $1.5 million in ARPA funds, the 7,700-square-foot housing resource center in the basement received more than $4.6 million, and the Westside Legends' home construction project saw more than $361,000 for two single-family homes on South Church Street and Daniels Avenue.

"This is just about complete, and I believe that people who are currently homeless or at risk of homelessness will be able to take these apartments in the very near future," Armstrong said, noting the supportive units and resource center that had a ribbon-cutting in late 2025.