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After 15 years as Pittsfield police chief, Wynn reflects on tenure before summer 2023 retirement

Pittsfield, Massachusetts Police Chief Michael Wynn and Mayor Linda Tyer.
Josh Landes
Pittsfield, Massachusetts Police Chief Michael Wynn and Mayor Linda Tyer.

The police chief of Berkshire County’s largest community is looking back on nearly three decades of service as he prepares to step down in July.

Michael Wynn told reporters at city hall Tuesday that he will relinquish the reins of the Pittsfield, Massachusetts police department on July 8th after one last day of service working the 4th of July parade next summer.

“I'd been thinking about it for a couple of years now, but obviously I've had recent changes in my family circumstances and family life," said Wynn. "And I had some minor health concerns this summer that caused me to reflect and reprioritize and it’s just, it's time.”

The 52-year-old chief did not elaborate on the specifics of his health concerns.

“I had an annual physical this summer, some of the metrics were moving in the wrong direction. And after a detailed conversation with my physician, there wasn't anything physiological," he said. "He basically said, your job is contributing to this.”

Wynn and his wife Christina revealed that they had adopted a child two months ago.

“So, I've been with the city since the fall of 1993," said the chief. "My first- Well, my second job, but my first professional job out of college was as the first director of the West Side Neighborhood Resource Center. That was half time for the first year and then full time for a year and a half after that. I was sent or selected to go to the academy in 1995, I graduated in ‘97. Or ’96, I'm sorry. I’ve been with the department since ‘95. Sergeant in 2001, lieutenant, approximately 2003 or 2004, captain in the summer of 2007. Before Chief [Anthony] Riello announced his departure, I took command in December of 2007, and permanent civil service chief on December 1st, 2017.”

The chief said flexibility is a crucial aspect of managing his department, which he described as unique to Massachusetts.

“I am the chief of the smallest agency in the Commonwealth that is considered a major city, but we police a city that is considered a large town," said Wynn. "And so, you need to be able to run investigations and supervise commanders who are running investigations of city type crime, and still make appearances at special events and be approachable and be accessible and be out and about.”

After an election cycle in Berkshire County that saw lawyer Timothy Shugrue elected District Attorney behind anecdotal claims that crime is out of control in the region, WAMC asked Wynn how he felt he was leaving Pittsfield – the county’s largest community – given that his department’s data shows a reduction in crime by almost 40% over the past five years.

“I think that we have to recognize that the last several years are an anomaly, right? The pandemic impacted a lot of things in ways we wouldn't expect," said Wynn. "And so, I don't know that the crime data that we're looking at accurately reflects, necessarily, the crime trends that we're dealing with. Certainly, what's been widely discussed publicly, and you've heard me talk about it, we have great concern about the amount of gun violence in the city and beyond. And, unfortunately, that gun violence is directly linked to the availability of illegal guns in and around the city.”

Before he leaves, Wynn says finishing the implementation of the city’s body camera programis one of his top priorities, and that installing his department’s fulltime training unit will likely be his signature contribution to Pittsfield. He also pointed to his efforts to encourage officers to seek mental health support and go to therapy on a regular basis.

“There's still a lot of stigma associated with dealing with mental illness and the effects of stress and post-traumatic stress," said Wynn. "And so, one of the things I'm most proud of is opening up that conversation, giving our people permission to say, look, boss, I need some help, and not worry that we're going to put them on restricted duty or, you know, take action against them.”

After a year where his department faced outcry over the killing of a city resident in the midst of a mental health crisis in March – 22-year-old Miguel Estrella – Wynn gave an update on the city’s efforts to expand its co-responder program.

“I met yesterday with the department's licensed social worker," said the chief. "We've onboarded him, so, I guess we can talk about it. So, we were fortunate that our first co-responder, Mr. Richard Collins, came out of retirement to take the position as the department social worker. And so, he's working with my command to do the screening process, the evaluation process. They've already interviewed candidates for the co-responders positions. And so, we're going through that now. We will come out of the out of this process with access to more social workers or clinicians and the ability to cover more shifts.”

WAMC asked Wynn to reflect on his regrets.

“I regret that it took us so long to get to full fleetwide implementation of the TASER program," he responded. "That was something we should have invested in right up front instead of piecemealing it. I regret that we haven't made more progress on pursuing a new station. I really hoped to have at least seen some shovels in the dirt on that when I took command.”

The outgoing chief says his command staff is working with the city on a transition plan. When it comes to finding Wynn’s successor, Pittsfield is still in the Massachusetts civil service system for its police department and is subject to its demands.

Josh Landes has been WAMC's Berkshire Bureau Chief since February 2018, following stints at WBGO Newark and WFMU East Orange. A passionate advocate for Western Massachusetts, Landes was raised in Pittsfield and attended Hampshire College in Amherst, receiving his bachelor's in Ethnomusicology and Radio Production. His free time is spent with his cat Harry, experimental electronic music, and exploring the woods.
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