Sycamore Police Chief Winters retires

SYCAMORE – Sycamore Police Chief Jim Winters officially retired Monday but the impact he made as the city’s top cop is poised to be his legacy.

The chief attended his final Sycamore City Council meeting Monday. The city appointed Erik Mahan, former deputy chief for the St. Charles Police Department, as successor.

After eight years at the helm of Sycamore’s predominant law enforcement agency, Winters said he felt now was the right time to step away from the role.

“I think the Sycamore Police Department is in great shape right now, but I also think that Chief Mahan will bring in more ideas and he’ll build on what I’ve tried to build on,” Winters said. “I’ve tried to build on what previous chiefs have built on.”

[ Sycamore police chief to retire ]

Winters credited Donald Thomas, who was Sycamore chief from 2001 to 2014, for bringing the department into the modern era through new policy and accreditation efforts.

ExpandAutoplay

Image 1 of 8

Sycamore Police Chief Jim Winters talks about some of his favorite moments throughout his career Friday, March 14, 2025, in his office at the Sycamore Police Department. Winters will be retiring later this month. (Mark Busch)

Winters, a Chicago Police Academy and Illinois State Police Academy graduate, started his career as a lawman in 1989 with the Bloomingdale Police Department before becoming an Illinois State Police Trooper. After working in suburban Cook County for a few years, Winters joined a tactical response, or SWAT team.

Seven years later, he went into narcotic investigations.

“I was very fortunate, I got to see a lot of different things between being on SWAT, between working undercover narcotics, between commanding a patrol district,” Winters said. “The state police really gave me a different variety, working with local police agencies, county police departments, special details, like the NATO Summit.”

Winters spent most of his career with the state police, where he rose to the rank of Lieutenant Colonel, in charge of field operations. But in 2016, he was appointed deputy chief in Sycamore, where he’d lived with his family since 1993.

By April of the following year, Winters was appointed interim police chief – a job he would take on permanently until he retired on Monday.

“You want to step away while you’re still contributing, and not go past a certain time where you should retire,” Winters said. “That was important to me, but more importantly for me it’s about the department.”

Winters said of all the counties in Illinois he’s worked in, DeKalb County is the best when it comes to law enforcement cooperation. He said working relationships between the DeKalb County Sheriff’s Office and other police agencies are strong in the county.

The relationship between Winters, DeKalb County Sheriff Andy Sullivan and DeKalb Police Chief David Byrd could be part of the reason that cooperation has been smooth in recent years.

Sullivan met Winters more than 30 years ago, before the sheriff began his law enforcement career.

“Even before my internship, I did a couple of ride-a-longs and one of the nights I was riding along with the Illinois State Police. It was Trooper Jim Winters,” Sullivan said. “That’s one of my early acquaintances that I had with Jim, even prior to him being one of my instructors at Kishwaukee College.”

Sullivan, who would go on to work with Winters at multiple stages in each other’s career, heralded the retiring chief’s professionalism, an particularly useful skill in police work.

“He always has a calming effect on things, especially when you’re in tense situations,” Sullivan said. “He’s always been someone that gives good guidance, and is I would say a very competent leader.”

Byrd also interacted with Winters early in his career with the ISP. While not in the same class, they occasionally crossed paths in the state police academy.

Byrd reckons they’ve worked closer than ever before.

“His ideas are extremely well thought out, you always know you’re going to get that with Jim,” Byrd said. “He really thinks out ideas, and he just doesn’t make rash decisions. He puts a lot of thoughts into his decision making, which is fantastic.”

Winters isn’t the only familiar face bidding farewell to the department to put on his retirement hat.

Jeff Wig, Sycamore’s deputy chief of police, said Winters remained “calm and level headed” over the nine years he worked with him. Wig also is set to retire this month.

“You don’t always know the decision he’s going to exactly make but what you can count on is consistency,” Wig said. “Things are, people and things are treated pretty much the same over the course of time. He’s very flexible, he’s open to new ideas.”

Winters will be retired for the next new idea, but said he has full trust in Chief Mahan, and the legacy he built at the Sycamore Police Department.

“To me,” Winters said, “it’s important that the department succeeds beyond me.”