- January 14, 2026
-
-
Loading
Loading
In the beginning of 2019, Windermere’s Jim O’Brien called then-mayor Gary Bruhn.
He was surprised to learn Bruhn, who had been serving as mayor for 15 years, was stepping down in the middle of his term.
“At first, I thought he was joking,” O’Brien said of Bruhn’s decision. “Gary was a quintessential small-town mayor. He had done it forever. … He was always my kids’ mayor. He and I agreed on a lot of things. We disagreed on a lot of things, but we always had a really healthy respect for each other.”
O’Brien had a question for Bruhn: Who is going to be mayor?
The response: You.
O’Brien was taken aback. He struggled with the idea of sacrificing more time than he already had as a Windermere Town Council member while juggling being a father and working full-time.
After some thought and a walk with former Mayor Gene Spears, who helped shift O’Brien’s mindset and realize the job of mayor didn’t have to be a full-time one, O’Brien felt ready.
He was elected mayor in March 2019.
Now, after serving as mayor for six years, O’Brien was the one making the phone call.
On the other end was fifth-generation Windermere resident and Windermere Town Council member Andy Williams, who will be the town’s next mayor.
O’Brien decided not to run for reelection, ending his 15-year stint of serving the town of Windermere.
O’Brien always had been interested in government. His grandfather on his mother’s side served as a town council member in Lake Park in the early 1960s, so he knew serving in local government was possible.
He already was familiar with local government institutions when he worked for Goodwill Industries and worked with the Orange County Board of County Commissioners, Orange County School Board and Windermere Town Council.
He used to watch government meetings on cable, even sometimes at nights when he couldn’t sleep.
O’Brien first dipped his toes in Windermere government by joining the Windermere Tree Board. He learned more about the town and how the Town Council worked. He also met more people in town.
In 2011, he decided to take his involvement a step further.
When O’Brien was deciding to run for Windermere Town Council, he had one goal in mind: He wanted the town to own the Ward Trail and create Windermere’s version of the West Orange Trail.
But after being elected to Windermere Town Council, the Ward Trail immediately was put on the back burner. He along with the rest of Town Council were thrown into turmoil.
The police chief at the time, Daniel Saylor, was fired after being arrested on charges of unlawful compensation for official behavior and official misconduct for shutting down a child-sex investigation of his friend, Scott Bush, who was arrested the same day.
The scandal rocked the 2-square-mile town.
And suddenly, the Town Council was responsible for rebuilding the foundation of the Windermere Police Department, reestablishing trust with the community and rewriting policies and procedures for the town.
The budget was tight. There was constant turnover on town staff and in the police department. Interviews were nonstop. Ultimately, the Town Council hired current Town Manager Robert Smith and Police Chief Dave Ogden.
They were building the foundation of the town.
“Focusing on those back-of-house items is what has allowed us to be successful,” O’Brien said.
Since then, town matters have calmed.
The biggest recent debates have been about boathouse ownership and Town Hall bathrooms.
“Part of being Windermere is we’re not looking to be in the news every day,” O’Brien said. “We want to be a place where you can raise your family, that is safe and secure, and you know your neighbors.”
O’Brien said since 2011, the town has worked to ensure transparency, accountability and professionalism, which were crucial to building faith in the community.
“It’s one of the things I’m most proud of, especially as a council person,” he said.
O’Brien first sat at the chair farthest to the left facing the stage in Town Hall. He felt it was the perfect vantage point to see his fellow council members while also being able to see everyone in the audience and their reactions to what was said.
Despite tradition being that as a council member’s seniority increases, the closer the council member sits toward the center, O’Brien refused to give up his post. The position helped him to know how to speak with his fellow council members and also gave him the first or last vote.
“I do think that is part of the success, being able to see people’s eyes and talk to them person-to-person,” O’Brien said.
He didn’t give up the seat until he became mayor in 2019.
Any time in a political office comes with the good times and the bad, and for O’Brien, it was no different.
“My whole thing is always the best and most difficult type of governing is the kind of governing where you walk out with the folks that you just walked in with,” O’Brien said. “There’s no separate exit. There’s no office to go disappear to. We live and play and work with all of the same people as our neighbors in town. That is one of the best parts and sometimes one of the worst parts of being in local government.”
He’s proud of several projects he completed while working as a council member and mayor. He attributes the dedication and determination of staff and Town Council members for the town’s progress over the past decade.
He focused on maintaining the town’s traditions while adding a twist of his own here and there, especially as the town grew over the years.
Light Up Windermere has grown in popularity and residents have been attending for years, but now, it’s more volunteer driven. A deejay and rock-climbing wall have been added over the years, but the town’s cake at the event and the town ornament always have been a tradition.
“We want that tie back to the past, we want to respect all of that as best we can but always be thinking forward, always be moving forward, never selling ourselves short,” he said. “It’s all about being small but smart. … It’s not about trying to be someone else that’s bigger or better or what have you. It’s about being what’s important for our town.”
He will treasure the memories of town staff and residents opening the time capsule from 1975 and watching the kids and adults alike go through everything in the capsule and listening to the words of Dean Kinzey, who was mayor at the time.
He will never forget being able to provide words of healing to the family of U.S. Army 1st Lt. Evan Fitzgibbon, who died during a Ranger School training incident, when a group of residents brought back Old Glory, a patriotic horse statue, to Windermere in honor of Fitzgibbon.
“Being able to speak to his memory and see everyone there so supportive of that family, that was just tremendous,” O’Brien said. “That’s an amazing opportunity to do some small amount of healing for a family that carries a burden that’s much larger than their share.”
With a town filled with engaged residents, community members with influence and a police department that makes everyone feel safe, O’Brien said it’s hard not to be successful.
“This is never about one person,” he said. “It’s never about an elected body. It’s never about one staff person. It’s always about the people. It’s always about what we all bring to the table together.”
There’s a sense of pride in being able to turn to a town committee that can provide suggestions and ideas O’Brien said he “would never have thought of in a million years,” giving good people the opportunity to shine and giving them the resources needed to be successful.
But it hasn’t always been easy.
Holding back tears, O’Brien took a moment to gather his thoughts remembering Windermere police officer Robert German, who was shot and killed in the line of duty in March 2014 while investigating two suspicious teen runaways who later were found dead from apparent self-inflicted gunshot wounds. German was the first Windermere Police Department officer to die in the line of duty.
“We’ve done our best to make sure we honor his memory and we use that terrible event as a positive piece of who we are, our DNA as a police department, our DNA as a community,” he said. “But that will always hurt.”
O’Brien said he always will lament the missed opportunity of the Healthy West Orange project in partnership with the Rotary Club of Windermere to build a pavilion in the green space behind Town Hall.
“We weren’t able to get that across the finish line,” he said. “I tried so hard to work out a compromise that would get us a project that would be worthy of those dollars and with the blessing of the town, and I wasn’t able to get it done. I think that’ll always be a disappointment.”
The ongoing challenge of serving as mayor is the role always is evolving, and there is no job description for mayor, O’Brien said.
“You never know what’s going to come around the corner, you really don’t,” he said.
O’Brien had been thinking of stepping down as mayor since the last election cycle, but he said he promised folks on the Centennial Committee he would wait until the town’s year of celebration was complete.
He said now is the right time to pass the torch. There are “strong people on council” and the town has a “very diverse council,” as well as talented leaders.
“There are folks who I can clearly see taking the gavel and running with it and doing a fantastic job of leadership and have the support of the community, as well,” he said.
O’Brien’s involvement in town matters will remain to be seen. He plans to spend more time with his wife, Kristin, as they now are empty-nesters, as well as with his father who has health issues. He also plans to get on the lakes Windermere is known for more.
And of course, he’ll be around if needed.
“This place will leave a mark on you,” he said. “It doesn’t turn off. … There’s always opportunities. My interest doesn’t go away. But I think I accomplished what I came to do. I hope I was a good steward of the town, not only of its resources but of its people and that we’re a little better off today than we were in 2019.”
Although O’Brien’s initial goal when running for Town Council was the Ward Trail, the project has yet to be finished. It has progressed, with the town owning the right of way and property from Sixth Avenue all the way to Windermere Elementary School and the town having $1 million in funding from Florida’s Safe Routes to Schools program and other funding sources. The trestle bridge has been picked out and ordered.
“It’s going to be everything that I always hoped it would be; it just took a little longer,” O’Brien said. “I kept staying (on council) to get that done. We were darn close, but I realized that if I stayed to get the whole thing done, I might be 80. … We’ll let our kids finish it up and bring it to fruition.”
