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Year In Review 2022: Police veteran LeGrady bids adieu as the town turns out to honor him

This story was published in January 2022.

“The heart of the community,” showed up at Police Department headquarters on a cold, bright Wednesday afternoon to honor Sgt. Terrence LeGrady and wish him well on his retirement, said Shelter Island Police Chief Jim Read.  

Chief Read was speaking about a long line of Island officers in front of the headquarters, joined by others from East End departments, plus representatives of the Island Fire Department, Emergency Medical Services, town government and school officials.

Sgt. LeGrady’s father, mother and brother were in attendance, as well as his wife Laura and their three sons. The widow of his fallen NYPD partner Officer Brian Simonsen, Leanne, attended, along with many other family members and friends.

Sgt. LeGrady is leaving after 17 years as a member of the department. Supervisor Gerry Siller presented a town proclamation thanking the officer for his exemplary service, noting his life-saving rescue of a boater and participating in the largest heroin bust in Island history, among many other accomplishments.

Supervisor Gerry Siller read and presented a Town Board proclamation with Police Chief Jim Read. (Credit: Ambrose Clancy)

Chief Read said, “Terrence personified the ideal police officer. His dedicated service to the department and the community were unmatched, and he held himself to the highest standards of professionalism in every action and public interaction. Sgt. LeGrady demonstrated the greatest pride for the department, and it’s been an honor to have him put on the uniform of the Shelter Island Police Department for the past 17 of his 22 years of police service. Sgt. LeGrady lived by his own words  — ‘What you do as a police officer each and every day matters!’ He’ll be missed by all who worked and served with him.”

Sgt. LeGrady’s wife spoke of the difficulties spouses and families go through with a loved one as a police officer, but also the pride those families have, and the joys she and her husband have shared throughout the years.

Laura LeGrady spoke about her husband and family. (Credit: Ambrose Clancy)

Sgt. LeGrady said he was grateful to the department, town officials and Islanders in general for the opportunity to serve them. He singled out Island EMT’s Mark Kanarvogel and Phil Power for their professionalism.

He also thanked his parents for instilling life-long values in him, and  expressed his gratitude to Laura for the love and support she continues to give him.

Sgt. LeGrady addressing the gathering. (Credit: Ambrose Clancy)

He spoke with emotion — pausing at times to gather himself — about Officer Simonsen — noting that the only negative aspect of his retirement ceremony was that he wasn’t there with him.

When he finished to spirited applause, Sgt. LeGrady came down the steps of police headquarters and embraced every officer who had stood throughout the ceremony.

A life in uniform

The years of his service to Island residents was proceeded by four years as a member of the New York City Police department, from 2000 to 2005.

“It’s time to go,” Sgt. LeGrady, told the Reporter earlier in the week, although he’ll miss his colleagues and coming in daily contact with Islanders. He lives in Calverton with Laura, and their three sons, Terrence Jr., 17, Conor, 14, and Drew, 13. The sergeant noted that he was the first police officer in the department who wasn’t an Island resident. “I hope I was a good test case,” he said.

The Island’s sense of self-sufficiency combined with a dedication to efficiency in its public services was an eyeopener when he first took the position as a police officer here. The department is organized so well, that “we seldom have to rely on other agencies or municipalities, like so many other places do,” he said.

He singled out the Island’s Emergency Medical Services. “EMS gets people to hospitals as fast or faster than most municipalities. They do a tremendous job.”

The Island as a whole has “great community collaboration in so many ways,” he added.

All in the family

Sgt. LeGrady comes from a background in law enforcement. Growing up in Centereach, his father was a NYPD officer. “I never knew anything but policing,” he said, noting that most of his friends in high school and college were all connected to law enforcement in one way or another.

At 23, he took the test to be a NYPD officer and soon was on the job. He remembered his father’s counsel when he started his career. “He told me, ‘Treat every person you meet with dignity and respect,’” Sgt. LeGrady said. “And he told me, ‘Look people directly in the eye. You can tell a lot from people’s eyes, especially if they’re friend or foe.’ I’ve found that to be true.”


There were three life-changing events during his NYPD duty. The first was meeting, working and becoming close friends with his partner, Officer Simonsen. Working out of the 102nd precinct in Queens, they became as close as brothers.

When Sgt. LeGrady left the NYPD to take the position with the Shelter Island department, he and his family moved to Calverton, and Officer Simonsen and his wife Leanne bought the house across the street.

“Our families were always together,” the sergeant said, in and out of each other’s homes, with all holidays spent together. The three LeGrady boys referred to Officer Simonsen as “Uncle Brian.”

The second life-changing event was the terror attack of Sept. 11, 2001. For the partners, it was nearly two weeks of practically non-stop duty. At times, they would go 40 hours without sleep, living on coffee and adrenaline at Ground Zero, sorting through the rubble for bodies.

And then, on the evening of Feb. 12, 2019, Officer Simonsen was shot dead investigating a robbery in Queens. Sgt. LeGrady, on duty on Shelter Island, was given permission to drive Ms. Simonsen to a Queens hospital to view his body and accompany Officer Simonsen home to be buried.

“He was the kindest, the sweetest man you’ll ever meet,” Sgt. LeGrady said.

Finding the Island

He left the NYPD because, he said this week, “I was looking for a better work environment. A place where I wouldn’t have to take my job home to my family every day. Laura and I talked about it and decided I needed to change.”

Taking the Suffolk County Police Department test, he scored 11th from the top, and received letters from several East End departments. “Laura and I had never set foot on Shelter Island,” he remembered. “We’d never even met anyone from the Island.”

He was interviewed by Chief Read and the Town Board, which acts as the Island’s police commission. “Both interviews were about half an hour,” he said. “I was very comfortable with Chief Read and the Board. They called right away and offered me the job.”

Now he’s focused on getting back into sales and event planning, which, “I’ve done on the side since 1992,” he said.

Recently, his oldest, Terrence Jr., expressed an interest in a career as a police officer. “I talked him out of that,” Sgt. LeGrady said. “It’s a noble profession, and the situation on Shelter Island is really unlike almost any other place. But unfortunately, there’s an anti-police sentiment, not here, but nationally. I hope it will get better, but as of now, it’s not improving.”

Leaving, he termed his experience working on the Island as “happy. And I hope everyone I came in contact with felt happy and safe that I was there, and that I helped them.”

A life in uniform. Sgt. Terrence LeGrady, left, soon after joining the New York City Police Department in 2001, and right, on the job with the Shelter Island Police Department. (Courtesy photo)