In honor of Sergeant Terrence LeGrady’s retirement, the Shelter Island Police Department will host a brief outdoor “walkout” and final salute on his last official day of work, Wednesday, January 12.
The events take place outdoors at SIPD headquarters beginning at 4 PM and include remarks by Town Supervisor Gerry Siller, SIPD Chief James J. Read Jr., and Sgt. LeGrady.
The ceremony will last no more than a half-hour, SIPD says. Due to the contagious nature of the omicron variant, attendees should wear a mask outdoors when proper social distancing cannot be maintained, Chief Read says.
Editor’s note: I got to know Terry when I first moved to Shelter Island full-time and wrote the weekly Police Blotter for The Reporter. We spoke on January 7, and this post is based mostly on that conversation but draws from past experiences.
About Sgt. LeGrady
Terrence LeGrady, 47, was born in Queens but grew up in Centereach from age 3. His father was an officer with the New York City Police Department, and LeGrady joined up after attending Suffolk County Community College (and doing a stint at UPS).
He served with the NYPD beginning in March of 2000, based largely out of the 102nd Precinct in Queens, where his father had been stationed. He served with the NYPD, but took the Suffolk County police exam and scored well. In 2005, he responded to a query from the SIPD which needed an officer but had no local candidates.
“I never stepped foot on Shelter Island until my interview,” he said. “I didn’t even know it existed.”
When Town Board members (in their capacity as police commissioners) interviewed him, they asked about possible East End connections.
No, he told them, he didn’t know the LeGradys from Orient. No, he was not related to the Sag Harbor LeGradys.
When he said his family was all from Queens, “their faces all dropped. They had a hard time understanding how it could be that I didn’t have any ties to the East End.”
Making the transition
He began his Island service in February 2005 (and was elevated to Sergeant in 2018).
Before hiring LeGrady, Shelter Island had changed its residency requirements. Officers no longer needed to live on the Island but had to live within the five East End towns.
“I was the first police officer they ever hired that did not reside on Shelter Island,” he said.
Within a year, he and his wife, Laura, moved with their then-18-month old son, Terrence, from Brookhaven to Calverton. (Terrence is 18 now, and the couple has two other boys: Connor, 15, and Drew, 13.)
Asked to describe the transition to Island life, LeGrady used two words: “Culture shock.”
“You can be the suburban boy who gets plopped into the city for the first time, which I did experience,” he said, recalling early days at the 102nd in Queens. “Then, you get the city boy who gets plopped into real suburbia. It was a little bit of culture shock at first.”
LeGrady, who was very close with his NYPD partner, didn’t know anyone. Read was Chief at the time, and other SIPD officers then included Jim and Tom Cronin, Chris Drake, Dave McGayhey, Walter Richards, and Jack H. Thilberg.
And, he had to learn a completely different way of policing, LeGrady said.
“I was used to certain types of crimes, certain types of calls. And, then coming out to Shelter Island, there were completely different types of calls and completely different people.”
It was, he said, “almost starting brand new.”
As an example, LeGrady told about an alarm call — “in the middle of the night, by myself.” It was a classic Shelter Island pitch dark, quiet night and the front door was open.
“As I was making sure the house was OK, there was some rustling in the bushes,” he said, thinking it must be the perpetrator. “It wound up being a deer.”
“Needless to say, it was as different as different could be,” he said. “But my heart was jumping out of my chest.”
‘The greatest show on Earth’
LeGrady said his instructors at the Police Academy referred to officers as witnesses to the “greatest show on Earth.”
After nearly 22 years, LeGrady said: “It was far from a circus, but it was the greatest show on Earth.”
“I have some of the funniest stories that unfortunately I cannot share with you,” he said. “Quite honestly, I also have some of the saddest, heart-wrenching stories.”
“I think I’ve experienced in my personal career everything that you can experience,” he said. “I can’t think of anything that another officer has told me that I don’t have some story or experience with.”
9/11
As many Islanders know, LeGrady was among the many responders to the September 11, 2001 attack on the World Trade Center.
He recently recalled the experience for Shelter Island students at a 20th anniversary 9/11 gathering. The outpouring of support from the public left a strong impression, he said, describing being hugged by crying strangers during a coffee break.
“We were thanked emphatically and had block after block of people chasing us and cheering us on, and these were people who didn’t have the best relationship with police,” he said. “It was amazing.”
But the sorrowful work of searching the wreckage was grueling, he said. Working double shifts in and around the pit at Ground Zero, he dug for possible survivors amid smoldering ruins and the reek of death.
And there were consequences to his own health. LeGrady was later treated for cancer he developed as a result of the response work.
At the anniversary gathering, he told students: “I hope this generation is never tested like we were on 9/11. But if it is, I hope that people put down their phones and help others. You need to act. If you think you are a good human being that cares for others, you need to stop what you’re doing and help.”
A fallen partner
The death of his former NYPD partner Brian Simonsen, killed by friendly fire while responding to a robbery in 2019, deeply affected LeGrady. He learned about it while on patrol here.
“I had the pleasure of working with him for a long time,” LeGrady told reporters at the time. “He could walk into any situation and as crazy as it could be, he had the ability to calm everything down without ever raising his voice.”
Simonsen grew up in Riverhead, and, after the LeGradys moved out East, Simonsen and his wife bought the house across the street. So close was the relationship, that LeGrady has described Simonsen as a brother.
When word of the tragedy spread, Shelter Islanders and residents across the entire East End of Long Island were incredibly supportive, LeGrady recalled.
“He was an absolutely beautiful human being,” he said. “He is greatly missed.”
A family legacy
LeGrady said the SIPD has been “extremely family-friendly; I am very thankful for that.” But recently, his eldest son told him, “I think I’m going to be a police officer.”
“Do you want to be with your kids on holidays and weekends?” LeGrady asked. “To have dinner with them and such?”
When his son said yes, LeGrady said, “Well, then don’t be a police officer.”
In response, his son said, “But, I’d like to honor you and Grandpa.”
“That’s fantastic,” LeGrady recalled saying. “But there are a million other ways you can honor me and your grandfather.”
Young Terrence, now contemplating college acceptances, instead is thinking about a career in education, following the path of his mother, who is a K-6 teacher.
Sgt. LeGrady said he has the highest regard for the SIPD and the Island community. But elsewhere, growing anti-police sentiment means a law enforcement career “is not a recommendation for my family.”
“I think policing, in general, is one of the noblest professions you can pursue,” he said.
“But it’s significantly changed within the last five years and there’s a sense of real anti-police in the country. And honestly, I don’t know that I’d want that for my children.”
A senior officer plans his future
Other than Chief Read and Detective/Sergeant Thilberg, LeGrady is retiring as the Island’s senior-most officer. (Anthony Rando is the new Sergeant.)
“When I graduated from high school, the majority of people I work with weren’t even born yet,” he said. “You start using references to certain things in life and you have these younger officers looking at you like deer in headlights. They have no idea what you’re talking about.”
In retirement, he hopes to turn side gigs as a DJ and former work as an event planner into a second career, describing it as “a lot of fun.”
“I’ve never really left it,” he said, of the business. “And I’ve been welcomed back with open arms.”
Among the gigs that he’s already lined up are perpetual appearances at the Shelter Island Lions Club annual Corn Hole Tournament, where he’s been DJ for the past three years. The event is organized by Chief Read, known to fellow Lions as the “Lion Tamer.”
“He doesn’t mind me retiring, as long as I come back for that,” LeGrady said.
Not easy to leave
As much as he looks forward to spending more time with his family and pursuing his other interests, LeGrady said it won’t be easy to leave.
“I don’t know if I can put into words how emotional it is to be walking out for the last time,” he said. “I’ve met some of the best people that I’ve ever come across in my entire life in the police department. They’re the most selfless people; they’re the most honest and caring and giving people. And those are very difficult people to walk away from.”
“They’ve truly influenced my life. Not having my old partner here is absolutely heart-wrenching,” he said. “And I can’t even begin to tell you how much it hurts in the celebration of leaving knowing that he should be with me. It’s as difficult as I can possibly describe.”
He said he wrote remarks for a retirement dinner, that had to be postponed due to COVID-19. Primary among those he recognized for support are his children and wife: “They deal with it as much as I do.” And, he’s grateful for the strong support network he’s developed here on Shelter Island.
LeGrady is a what you see is what you get kind of a guy. He wears his heart on his sleeve and prides himself on being truthful.
“I hope that I left a decent impression on people,” he said, as our interview concluded. “I hope I always did right by them. If they ever needed me for something, that I was there. And I hope they always knew that I treated them as fairly as I possibly could.”
