Meet the new mayor: Jim O'Brien ready to serve Windermere

Windermere Mayor-elect Jim O’Brien is preparing to officially step into his new role on Tuesday, March 26.

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  • | 4:36 p.m. March 20, 2019
  • Southwest Orange
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There’s a new mayor in town, and while he might not be sporting colorful pocket squares, he is ready to serve nonetheless.

Windermere Mayor-elect Jim O’Brien previously served as a town council member for eight years and will officially be sworn in as mayor on March 26. He takes the place of retiring Mayor Gary Bruhn, who has led the town for 15 years.

O’Brien is a native of West Palm Beach and received both a bachelor’s degree in social work and a master’s degree in education from Florida Atlantic University. He worked in nonprofit in south Florida for a few years until he and his wife, Kristin — a Windermere native — married in 2005. 

When O’Brien visited Windermere and got familiar with it, he and Kristin knew it was the perfect place to raise their family.



For O’Brien, public service always had been something that interested him. His grandfather was a county commissioner in south Florida in the 1960s, and O’Brien shared that same interest in local politics.

“I liked that it was more community based,” he said. “I started going to Town Council meetings and learning a lot about the history of town and the community.”

After joining and serving on the town’s tree board for a while, he decided in 2010 to make a run for Town Council, to which he was elected in 2011.

He was elected during what was a tumultuous time for Windermere. But to O’Brien, that only made his service more important. During his first term he helped rebuild the town’s foundation. Windermere got a new police chief and a town manager, and the council members helped review and revise town policies.

“The first couple of years we really spent that time working on the foundation of what it takes to have a good town or municipality,” he said. “Those are the kinds of things we worked on. It gave me a real appreciation and understanding for the nuts and bolts — you understand budget, policies, purchasing, all the things you really need to understand in order to have that big-picture view of what it is we’re trying to accomplish. …I think that we were able to use that base to kind of make sure we made good hires, invested in our people, (to make sure) that we were careful with the budget and that we did those things that set us up to be where we are today.”

Fast forward to the end of 2018, when outgoing Mayor Gary Bruhn announced to town staff that he would be retiring and moving to a new home just outside the town limits. Originally, O’Brien said, he was so surprised that he thought it was a joke. The next question that he — and the entire town — seemed to be asking, though, was the same one: Who was going to be the next mayor?

“I didn’t set out to do (public service) to become mayor,” he said. “I feel like it more came toward me. Doing this is something I’m really passionate about, but it takes the one commodity you can’t create any more of and that’s time. I have a young family and a job that I have to work to pay the bills that I enjoy. … By the same token, a lot of people were saying, ‘Hey, you should really think about this.’ I got a lot of encouragement from people I respect and trust. 

“Mayor Bruhn was supportive,” he said. “I called him, and I asked what he was thinking, and he said: ‘I think you should do it. You’ve been prepping for it for eight years and have always shown good temperament and a steady hand.’”

With encouragement surrounding him from Bruhn, his family, friends and many in the community, O’Brien decided to take the opportunity.



One of the things Bruhn has taught him over the years, he said, is that public servants need to be thinking all the time and ensuring that they’re present in both the local and greater communities. 

“I don’t know how he does as much as he’s able to do,” O’Brien said. “He’s at every single event, and he’s here to do the work. He really goes out, and he’s the leader. He participates and listens and is very engaged, and I’m going to do that to the best of my ability. We sure appreciate him doing that, and he’s really put us in a good place to continue to move forward.”

One of the most important things O’Brien hopes to do is help keep Windermere small but smart. The goal, he said, is to continue to grow the town’s infrastructure at the right level, make the right investments, have the key personnel needed and keep the same community feel that people love.

“It’s just a little slice of peace in all of the activity that goes on around us,” he said. “We’re really fortunate to be in West Orange. …That’s the beauty that Windermere brings with it. It’s not just buildings and trees; what makes it work are the people that give back to it and are passionate about and committed to it.”

His first priorities upon officially stepping into his new role are working with staff to continue promoting transparency and efficiency in communications, as well as improving communications with residents and increasing volunteer-committee participation.

Another important issue, he said, is keeping on track with various pieces of infrastructure improvement in terms of water and sanitary sewer, as well as keeping up with roadways and town facilities.

“One of the pieces we’re working hard on is that we’re in a difficult spot with traffic here, but it doesn’t mean we don’t need to continue to address it,” he said. “I think we’ll have to do that in a multitude of ways, some smaller and some bigger. … It’s my hope that we can make some inroads there in terms of as much mitigation as possible. It’s a pretty big challenge, and I know it frustrates people, whether you live here or don’t.”

Finally, he said, he hopes to encourage input from residents — specifically in having them bring potential solutions to the table when discussing an issue. 

“I think we have a lot of talented folks in all different spectrums and we could certainly benefit from that,” he said. “The six folks who sit up on Town Council don’t have the answers for everything, but we certainly can act as the conduit to move those things forward.”

Looking ahead, O’Brien said he knows he has big shoes to fill. However, he also has a great support system behind him in the form of family, friends and neighbors.

“I’m appreciative of all the kind words and support that I’ve been given, not only now but over the past eight years, and I’m appreciative for some of those tough words, too,” he said. “I listen to them and learn a lot. I appreciate everyone’s confidence and faith. I’m going to work hard to do a really good job and continue to make us proud and make sure we’re a place where everyone wants to be.”


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