'Highly Decorated' Pittsfield Police Lt. Michael Winston dies

Pittsfield Lt. Michael Winston talks with third-graders at Crosby Elementary School in Pittsfield in 2014 as part of Read Across America Day. Winston died Friday while on vacation in Florida.

PITTSFIELD — City Police Lt. Michael Winston, who has served on the department for nearly 24 years, died Friday morning while on vacation in Fort Myers, Fla. He was 55.

Winston, a resident of Lanesborough, died of an unspecified medical issue, according to Chief Michael Wynn. An official cause of death has not yet been determined.

A "highly decorated" lieutenant, Winston most recently was working as the commander for the department's midnight shift and a member of the internal affairs team, Wynn said.

He has also served as commander of the Berkshire Special Response Team for more than 10 years, said Wynn, who's worked with Winston since the early 1990s.

"In that capacity, he did a lot to improve and enhance the capabilities of the team," Wynn said.

The special response team is a highly trained, specially equipped unit that responds to incidents that exceed the capabilities of standard police resources.

"The team's really improved (under Winston); now it's a countywide team," said Pittsfield Police Sgt. James Roccabruna, who graduated the police academy with Winston in 1994. "The equipment he helped the team get is just unbelievable compared to what we used to have."

As a group, the six Pittsfield officers who graduated the 1994 academy have spent a lot together over the years, including getting their master's degrees, working night shifts, and serving on the special response team, according to Roccabruna.

While "jovial and friendly" in his downtime, Winston was the "manifestation of professionalism" on the job, Wynn said.

Over the years, the lieutenant, who worked as a truck driver before going to the police academy, brought on new equipment and command protocols to the department, Wynn said.

He started at the Pittsfield Police Department in June 1994.

In his tenure, also served on teams that protected first ladies Hillary Clinton, Laura Bush and Michelle Obama during their visits to the Berkshires and regularly planned and oversaw details for the annual Fourth of July Parade, Wynn said.

Wynn, who worked alongside Winston when they were patrol officers, said on New Year's Eve they reminisced about being partnered together during a First Night celebration in the 1990s.

"Because he's 6 feet 5 inches and I'm like 5 feet 6 inches, somebody thought it would be hysterical," Wynn said, adding that a "Mutt and Jeff" reference stuck around despite rarely being partnered together after that.

Winston leaves behind his longtime partner, Kate Gleason, as well as his three daughters and a son. His youngest child is a senior in college, Roccabruna said.

Outside of work, Winston, a Red Sox and Pittsburgh Steelers fan, was dedicated to his family.

"He coached his kids' Little League teams all the way through," Roccabruna said. "He was always talking about his family."

Winston would pick up extra hours at work to make sure that his children had what they needed when they were growing up, whether it be a baseball bat for his son or violin lessons for his daughter, Roccabruna said.

"Hes really going to be missed," Roccabruna said. "He was a big part of the department."

Haven Orecchio-Egresitz can be reached at horecchio@berkshireeagle, @HavenEagle on Twitter and 413-770-6977.