New Winslow Police Chief Len Macdaid in his office at the Police Department at the Winslow Town Office in Winslow. Abrahamson/Morning Sentinel Buy this Photo

WINSLOW — In his 20-plus years in law enforcement, Leonard Macdaid found a passion for community policing. With his experiences in Newport, Clinton, Lewiston and with the Somerset County Sheriff’s Department, Winslow’s newest police chief looks to entrench himself in the community to meet its needs.

Macdaid’s contract was approved at the Oct. 13 Winslow Town Council meeting. The 59-year-old Portland native assumed his post the next day. Macdaid replaces Shawn O’Leary, who retired earlier this year. Cpt. Haley Fleming served as interim chief.

“I’ve always tried to become a part of the community,” Macdaid said in an interview in his new office. “What people don’t understand about community policing is (that) … what I feel is an important need as a police officer might not be what the community needs.”

Macdaid gave a simple example. An elderly person having a plant stolen off the porch isn’t a major crime. The plant may be worth only a few dollars, but it may be the only interaction the person who had the plant stolen has ever had with police. That interaction is important.

“We have to take that very seriously and basically make sure that we take it as seriously as any other complaint and go back,” Macdaid said. “Even though the chance of us solving that might be little to none, going back and spending time with the person, it at least can let them know we’re trying.

“Every community has different needs,” Macdaid said. “I’m not really sure what the needs are in Winslow, and that’s why I have to get down here and after a while assess what’s going on, and then try to adapt for what needs to be done here.”


Macdaid commended the officers at the Winslow Police Department for helping ease the transition. Over his first three weeks and in the future, Macdaid looks to build a working relationship with his staff, town office staff, town councilors, the school system, business owners and Winslow residents.

Macdaid described his leadership style as one that encourages teamwork.

“I believe that we’re all equal, and no one is more important than anybody else,” Macdaid said. “If I can’t build a strong relationship with the town officials and council people, then I am wasting my time. The town leaders know the town a lot better than I do.”


Macdaid graduated from Cheverus High School in Portland in 1980. From there, he spent four years in the U.S. Navy submarine service and went to night school to earn a degree from Husson University. Macdaid then worked as a police officer in Lewiston before taking a position as a detective at the Somerset County Sheriff’s Department. From there, he worked as an officer in Pittsfield.

Macdaid’s assumed his first police chief position in Clinton in 2000. He recently finished his 15th year as the police chief in Newport.


Newport Town Manager Jim Ricker hired Macdaid to replace himself after 25 years as police chief.

“I had conducted quite a background on his ability to lead and his relationships with the Maine Chiefs of Police, and I was quite impressed with him and his desire,” Ricker said. “He did an excellent job with the police department as far as personnel, keeping up with all the training that is crucial today. He was very fair, I think, in dealing with his officers and … what I consider to be an asset in the community.”

When Macdaid talks about community policing, his message is simple. He strives to meet the needs of the community. While he is still learning what Winslow’s specific needs are, Macdaid has a track record of changing the communities he works in.

“I’ve known Lenny for many, many years, and he’s always been a guy that has done his job well and done it professionally,” said Ed Tolan, executive director of the Maine Chiefs of Police Association and former police chief in Falmouth. “I think it is great that he is the chief up there. We recognize his leadership capabilities.”

As a young officer in Lewiston, Macdaid taught law classes with colleagues at Lewiston High School. He also helped found the state’s first bicycle patrol unit and traveled across Maine to teach other departments about implementing bicycle patrols.

With the Somerset County Sheriff’s Department, Macdaid served as a juvenile officer. He helped start the Drug Abuse Resistance Education (DARE) programs in Bingham, Jackman and Pittsfield.


In Pittsfield, Macdaid started a branch of the Hooked on Fishing — Not on Drugs program, an endeavor sponsored by the Maine Department of Inland Fisheries & Wildlife that teaches children to fish, solve problems and make decisions and helps build self-esteem. Macdaid helped found the school resource officer program in Newport and also coached youth football and baseball.


Macdaid described taking the Winslow job as “a natural transition.” When he started in Clinton, Macdaid was the department’s lone employee. The town experienced turmoil in that area before he got there. When he left in 2005, Macdaid had accomplished his task to “build a police department.”

Macdaid worked as a patrol officer in addition to performing chief duties. By 2005, he had three full-time officers and seven part-timers and an animal control officer.

Newport’s police force had six full-time officers. Winslow has 11 full-time officers.

“I thought coming here would be a great challenge and also would give me the ability to be more of an administrator,” Macdaid said. “When you’re at a smaller department, you can’t do some of the bigger projects you want to do as a police chief, because you’re so busy covering patrols.”


Macdaid anticipates zeroing in on larger projects when he has a better understanding of Winslow’s needs. He is passionate about working with children and the elderly, as well as working with residents with mental health conditions.

“If you look at what’s going on across the country, way too many times police departments are interacting with people that have an illness, and we’re a lot better now than we used to be, but it’s very important that we get better,” Macdaid said. “Across the country, too many police officers end up getting in deadly situations with someone who is mentally ill. We’re working very hard in the state to change that.”

Macdaid said he, in conjunction with the Maine State Police, hopes to find a way to clearly identify if someone has a mental health condition and what steps to properly address and work with those people.

“If everything gets here that needs to be done, then I would try to do some of that stuff,” Macdaid said.

Over the past three weeks, Macdaid has ridden with other police officers to get a better sense of the community. He is in the process of moving to Winslow.

“Winslow is a very proud community with a strong history and traditions. I’m looking forward to being a resident here and basically becoming a part of the community.”

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