Hundreds pay respects to Pittsfield Police Lt. Michael Winston

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PITTSFIELD — Red and blue lights blazed, mirrored in a million raindrops as the funeral procession wound its way down Pontoosuc Street toward St. Charles Church. 

Over 800 people attended a funeral Friday for Lt. Michael Winston, a longtime Pittsfield police officer who died last week of a heart attack while vacationing in Fort Myers, Fla. Described by Chief Michael Wynn as "highly decorated," Winston, 55, was the midnight shift commander, as well as commander of the Berkshire Special Response Team for 14 years.

A horse carrying a member of the Berkshire County Sheriff's Department whinnied as officers carried Winston's casket toward the door of St. Charles. Scores of officers stood at attention as rain dripped from their caps.

Once inside, three members of the Pittsfield Police Department Honor Guard saluted Winston, laid "ready for his final inspection." 

Dignitaries among the crowd included Mayor Linda Tyer, State Sen. Adam Hinds, State Rep. Tricia Farley-Bouvier and hundreds of first responders.

"And so we share this wonderful man, Lt. Michael Winston," said the Rev. Peter Gregory, noting the proximity of Winston's passing to the Christmas season. "On that morning, a week ago today, the gift of Lt. Michael Winston was given over to the Lord." 

During the sermon, a flash flood warning reached every cell phone in the room, but this time people's attention was elsewhere. 

While Winston cannot be replaced, Gregory urged his longtime life partner, Kate Gleason, to think of him when she sees an eagle perched near the home the couple just erected.

"I want you to enjoy the beach home that was just built on Pontoosuc Lake," he said. "He will raise you up on eagles' wings." 

Pittsfield Police Sgt. Jim Roccabruna said he worked alongside Winston since they met at the police academy in 1994. He said it was apparent early on that Winston was a tough one to crack. He said Winston's height won him additional attention from the drill instructors, one of whom he recalls stepping on his lunch box to scream at him at eye level.

Winston's only reaction came later, Roccabruna recalled, with deadpan delivery: "that trooper broke my juice box." 

Roccabruna said Winston was "calm in the face of everything." He remembered one Fourth of July shift in particular, when Winston's stoicism saved the day. He said a crowd had formed around a woman yelling at her son's father, a very large man, and they were having a tug of war over the crying baby, whom the father was holding "upside down by one leg." 

The woman said he'd just smoked crack cocaine, and the situation was tense.

"Mike just kept talking to him in a calm voice," Roccabruna said, assuring him "that we would work it out."

"Finally, the man relented," he said. "He was placed under arrest without further incident."

In the department, Roccabruna said, Winston has won the Terry Donnelly Award, and in 2013 was selected to help guard Michelle Obama during her visit to the city. 

Winston "loved walking the North Street beat," Roccabruna said, and as commander of the Berkshire Special Response team he turned a "black pajama gang" into a well-respected team with appropriate equipment.

While Winston was dedicated to his work, Roccabruna said it was always clear his family came first. After the youngest of his four children grew old enough to leave home, Roccabruna recalled how he got to work outfitting the new lake house with jet skis and "the whole nine yards."

"He said he wanted to make sure they'd always come home," Roccabruna said.

Gleason, speaking with emotion and through tears, remembered her partner as "our hero." The sound of crying echoed from pews to the church's high ceiling.

 "He supported our kids in everything they did," Gleason said during the ceremony. "As heartbroken as I am today, I am equally grateful ... how lucky I've been to have him by my side."

Gleason said Winston delighted in his role as grandfather and always supported his daughter's violin talents. To his son, Andrew, he gave his "devastating good looks."

"Those were Dad's words, not mine," she said, eliciting tearful laughter from the crowd.

"His spirit lives on," Gleason said. "This world is a better place because Mike Winston lived in it." 

Reach Amanda Drane at, @amandadrane on Twitter or at 413-496-6296. 


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