When his two sons, Rory and Ryan, joined the Southold Police Department, newly retired police chief Martin Flatley gave each young man a list.

“I gave them a list of different things to keep in mind throughout their career,” he said in an interview last week following his retirement ceremony. “Things like taking an arrest very seriously — because you’re taking away someone’s freedom, taking away someone’s liberty. Don’t get into writing tickets just because you feel like you have to write tickets. You make sure you can get behind it. Just because someone looks different or has a different point of view, treat them all the same until you have some reason to believe otherwise. Things like that.”

As he heads into retirement after 47 years with the Southold PD — the first three as a seasonal officer — the former chief said he’s proud of his sons and their fellow officers as he hands the department over to a new generation.

“It’s kind of funny to watch them,” Mr. Flatley said. ” You see them as high school kids, and then get to the point where they’re young police officers, and to see how they do on the road.”

The Southold Town Board announced last month that Captain Steven Grattan would succeed Mr. Flatley as the town’s new police chief.

“We are losing the institutional knowledge of 47 years of working for this agency,” Mr. Grattan said last week. “He has a wealth of knowledge and knows the inner workings of this agency better than anybody else.”

Mr. Grattan described his predecessor as a “great, great person — always has a kind demeanor, always treated everybody fairly, respectfully. He’s very patient and just an approachable guy.”

Other local officials also hailed Mr. Flatley’s long service to the community.

“He’s dedicated his life to this town, through his job, and it’s just been an amazing career for him,” said veteran Town Board member Jill Doherty, who was first elected in 2011, the year Mr. Flatley became police chief. “He’s done a lot of good things, and he didn’t just police. He took the role of chief very seriously [and] did every aspect of it. He joined committees in the county to get funds and grants out here on the East End. He really worked hard at it. And he was there for you 24/7, basically.”

When Mr. Flatley — then a college sophomore — joined the Southold Police Department as a summer officer in 1977, Southold cops carried revolvers and filed reports in carbon copy at the end of shifts, dealing largely with property crimes and local nuisances.

Nearly half a century later, the chief retired last month after leading the department through a revolution in policing technology that reshaped law enforcement nationwide, with electronic reports and license plate scanners, among other technological innovations.

Southold was one of the first area police departments to start using dashboard cameras, and earlier this year received nearly $1 million in state grant money for body cameras and the equipment needed to store and manage the data. Town officers also use license plate readers mounted on patrol cars, as well as stationary LPRs posted throughout the region as part of an initiative of Suffolk County District Attorney Ray Tierney’s office.

Mr. Flatley’s affection for the police department he has called home for decades — and for policing itself — is clear.

“I consider myself very lucky,” he said. “I held each one of the titles in our department, so I always felt like I had a good understanding of each one of the offices, because I was there at one point in time.”

Still, he said, his time as a police detective, during which he worked with regional task forces, was the most compelling and rewarding.

“It’s just nice to be able to sink your teeth into a case and follow it from beginning to end and really put the efforts into to one case like that, rather than bouncing around from call to call to call when you’re in patrol.

“The detectives’ office was definitely the best, and working with the [East End] Drug Task Force was a really good experience, because I’d get to go up on bigger cases and do wiretaps and that type of thing. It’s a good experience I would have never gotten just being in Southold.”

Mr. Flatley said the concept of law enforcement task forces on the East End “makes sense.

“A department our size couldn’t have a narcotics division, do undercover buys and that type of thing. So if you put one officer from each of these [East End] departments into a task force, it’s a good fit.”

He said North Fork detectives would work undercover on the South Fork where they were less likely to be recognized as cops, and vice versa.

“The concept is a good one for the East End.”

Mr. Flatley said the most vital component of any successful police department is the quality of the officers.

“I really dwelled on trying to hire young officers that were good personalities and very community-oriented and could carry that community-oriented policing model with them, and I think we’ve done a pretty good job doing that.

“Our officers live in the community. They work in the community. They respect the people in the community that they live in. So I think it’s the quality of the officers that are coming through now, and what you try to instill in them that’s helped our department.”

He said today’s police officers have a level of training and education that wasn’t present in local police departments when he started out, which were far more reactive to crime than more proactive modern day policing strategies.

“Then, it was a lot of older guys, and a kind of ‘us vs. them’ mentality,” he said.

“Today, it’s a totally different job — from de-escalation skills and being able to talk somebody down, or dealing with people with different disabilities that may present differently on the street. There’s definitely more of a social awareness and how to deal with people with behavioral disorders.”

He said the job is “a lot more complex than it was in the ’70s and early ’80s, in a good way.”

Crime became more complex, too — especially cybercrime.

“When I first came on, if somebody wanted to make money illegally, he would stick up a liquor store or rob somebody on the street. Now, for people making serious money committing crimes, they steal an identity … and they’re able to steal thousands or hundreds of thousands of dollars — even a million in some cases — without ever having to show their face or be personally involved in the crime,” he said, referring specifically to elder fraud.

“One of the most frustrating [crimes] to me is the fraud cases that are going on now,” referring to phone and internet scams targeting the elderly, which are often hatched overseas. “We have somewhat of an older population that are [being victimized]. It’s crazy and it happens all the time.

“It’s frustrating because when you try to investigate them, no matter how much effort you put in, you almost always come into a dead end because they’re operating under a stolen identity and it’s very difficult to actually arrest someone.”

Mr. Flatley said that what he’d miss most about the position is “all the people that you meet, all the meetings you speak at.

“I’ll definitely miss the officers at work. I’ve always enjoyed the work. Some of the side stuff and the politics and that type of thing can be cumbersome and kind of wear you out after a while. But I’ve always enjoyed interacting with people, especially going to the Strawberry Festivals, the Maritime Festivals and fairs like that, where we actually get to go out and spend time in the public and talk to everyone, and get feedback from everyone. I’ll definitely miss that.”

Mr. Flatley’s retirement is part of a disciplinary agreement that included a 70-day suspension in 2022 over the department’s handling of complaints about a sergeant’s retirement party during the pandemic lockdowns of 2020, an incident for which Mr. Flatley issued an apology.

Longtime Greenport trustee Mary Bess Phillips said she would miss the chief.

“I hope he enjoys retirement, but I think he still has a lot to give to our community, both the Village of Greenport and the Town of Southold,” she said. “And I hope that he sees his way to help guide us through a lot of new situations that are happening in our township, that our growing pains are causing.”

Mr. Flatley’s retirement may not be the end of his policing career.

“I haven’t decided on anything right yet. It’s just been a week now, but I’m not the type that’s going to sit home and do nothing either, so I’m probably going to look around,” he said. “I’ve had some discussions with people about other employment. So I’m going to keep my ears open and kind of hopefully pick something else that would keep me interested for several more years.”

In the immediate future, though, golf and grandkids are in the cards.

“I have to pick up golf,” he said. “I’ve always liked playing golf and I’m going to have the time to do it now. So I’ll pick up things like that. And spending time with my grandchildren always makes me happy.”