Wynn has been a part of the Pittsfield PD for around 30 years, and at its head since 2007.
Despite criticism of his department’s financial accounting, the chief saw his budget grow year over year over his tenure. In fiscal year 2016, it was set at $9.2 million. For fiscal year 2024, it sits at around $14.3 million.
In December, Wynn held a press conference in Mayor Linda Tyer’s office to announce he would be stepping down on July 8th after a ceremonial transfer of authority to his successor during the city’s annual 4th of July parade. He cited family and health as the chief motivators behind the move.
“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.”
Tyer, who is stepping down at the end of the year after eight years in office, says the winner of the upcoming mayoral election will help determine Wynn’s replacement.
“I'm hoping that as soon as the next mayor is elected, that very shortly thereafter the election, that person and I can work together to establish the protocols and the criteria for the assessment center that would be held to select the next chief of police so that as soon as possible in January, that assessment center can be held and the next mayor will have a list of candidates to choose from,” she told WAMC.
In the interim, Tyer elevated Captain Thomas Dawley to take over leadership of the department. Dawley spoke with WAMC in April about his goals.
“The men and women of the Pittsfield police department are the most important to me right now," he said. "I want to make sure that every need and every want that they request is met in terms of training, what they want to see in the rank and file with our department. I just want them to know that I'm here for them if they need anything, and building that relationship with my officers will certainly spill over to the public, and that transparency, that empathy, that understanding, to deal with day in and day out situations, I think it's going to be definitely coming from the top down. So, we're going to look at, you know, we really want to focus on getting our policies and procedures in order. The body worn camera program, we want to get that up and running.”
Wynn led the department during two high-profile police killings of residents experiencing a mental health crisis: Daniel Gillis in 2017 and Miguel Estrella in 2022. Despite reports from friends, family, and law enforcement all confirming that Estrella was self-harming prior to his death, was in a manic state, and had a history of mental health struggles, Wynn’s department retroactively determined in an internal investigation that he did not quality as a “person in crisis” when police shot him. Wynn defined the term in an interview with WAMC about the report that exonerated the officers.
WYNN: We're looking at a person in crisis, who could be anybody who is experiencing a mental health episode, substance abuse episode, or some other type of episode that the particular policy that was impacted – in this case was our policy on civil commitments, or Section 12s – and that policy specifically references substantial risk of physical harm to the person as shown by his or her threats or attempts to commit suicide or cause other serious bodily harm to him or herself, a substantial risk of physical harm to other persons as shown by homicidal or other violent behavior, or evidence that others are in reasonable fear of violent behavior and serious physical harm, and when the person's judgment is so effected that there is substantial risk that the person cannot protect him or herself from physical impairment or injury, and there was no reasonable provision for protection available in the community.”
WAMC: And what is that definition from?
WYNN: That's from our civil commitments policy.
I think that part of the report was the part that most stuck out to me, this idea that- The different descriptions of Mr. Estrella versus the declaration that he did not qualify for that definition. That's where I find myself confused as someone who has been following the official narratives since the beginning.
WYNN: I can understand that, but again, I can't comment on an ongoing investigation.
In June 2020, Wynn – like many law enforcement leaders across the United States – helped propagate a hoax about leftist demonstrators co-opting local Black Lives Matter rallies for violent purposes promoted by then-President Trump. WAMC broke the news that Pittsfield had even requested an increased state police presence over the fictional threat despite evidence that it was suspect. Wynn – who referred to city councilors skeptical of the threats posed by BLM rallies as “insane” in emails obtained by WAMC – subsequently admitted that he had been wrong.
“In hindsight, we probably just should have stuck to the categorization of ‘agitators,’" he told WAMC. "But in the conference call, Zoom call that we were in, Antifa was the descriptor that was used, and it was the descriptor that I repeated and passed on. You know, that may have been an error.”
WAMC asked Wynn if he had any regrets as he prepared to step down at his December press conference.
“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.”
In June, Tyer recommended the city council subcommittee on ordinance and rules raise the chief position’s pay and end a residency requirement for the job. Council members did not support bringing the changes before the full body at that time, citing a need for more discussion.
