WINSLOW — It has been the professional goal of Shawn O’Leary to be a police chief.

On Monday, O’Leary, 47, was approved by Winslow’s Town Council to become the new police chief, effective May 12.

O’Leary’s hiring comes a little more than two months after former chief Jeffrey Fenlason resigned abruptly in February. Town Manager Michael Heavener was interim police chief during that time.

A veteran of more than two decades of law enforcement, O’Leary has risen steadily up the ranks of department positions, starting as a reserve cop in southern Maine for several years, working as a reserve officer in communities that have heavy summer activity.

“I was a summer cop, or a rent-a-cop, as they used to call them — or still do,” said O’Leary, a Lewiston native who lives in Topsham with wife Heidi, and two children, Meaghan, 18, and Matthew, 16. “Doing that reserve work, I really got that bite.”

In 1988, O’Leary was a full-time officer for the Brunswick Police Department, working as a patrol officer while also working with the Maine Drug Enforcement Agency.


“The good thing about my time there, I did 20 years on patrol, working up to patrol lieutenant,” he said. “I had a lot of collateral duties. I was on the bike team, the special response team and worked in undercover operations for MDEA.”

In 2008, O’Leary joined the Cumberland County Sheriff’s Office, working as the captain of criminal investigation.

“My first role in Cumberland was for support services, which meant I took care of all training and grant writing and hiring,” he said. “I had a broad base.”

It’s O’Leary’s experience with many different responsibilities in law enforcement that made him a suitable applicant, and he was the unanimous first choice for the search committee, which included Heavener, councilors Kenneth Fletcher and Gerald Saint Amand and resident Sally Harwood.

“He’s very well-rounded with both his knowledge and experience,” Heavener said.

Heavener said the vacancy drew 42 applicants, which were narrowed to 27, then 10, before the top five were brought in for interviews.


After working in Brunswick, which has a population of about 20,000, and at the sheriff’s office in Cumberland County, which is the state’s most populous county, O’Leary is looking forward to working with a smaller, close-knit community. Winslow has a population of about 8,000.

“Where I’m currently at in the sheriff’s office, it’s a bigger area and extremely busy,” he said. “You can’t really see the day-to-day operations.”

O’Leary said he’s excited about forming relationships with his new staff and the surrounding community, both of which he feels are vital components to a well-run police department.

“I know there’s some really good talent here. I think it needs to be harnessed and utilized and nurtured,” O’Leary said. “I associate being a supervisor with being a parent. You need to raise them, teach them, give them guidelines and give them space.”

One of O’Leary’s early goals is to establish a local program, Coffee with a Cop, in which he and sometimes another officer meet at a local coffee establishment and have conversations with the public.

“I think some members of the community may be intimidated by police or feel uneasy,” he said. “Having just a cup of coffee, you can really get to know people and solve a lot of problems.

“I want my door to be open to the community members,” O’Leary continued. “I want to meet as many business owners and community leaders as possible. That’s one of my goals this first year.”

O’Leary is scheduled to be sworn into office May 12.

Jesse Scardina — 861-9239jscardina[email protected]Twitter: @jessescardina

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