- March 27, 2026
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Chip Wilson, Orange County District 1 Commissioner Nicole Wilson and State Rep. Leonard Spencer attended the farewell party to honor a fellow political figure former Mayor Jim O'Brien.
Anne and Derek DeBoer were thrilled to celebrate their friend and neighbor of nine years, Jim O'Brien. "He is the biggest part of why we have felt so welcome in this town," Derek DeBoer said. "He is an incredible person."
Lavina Williams, Pam Martini, Colleen Williams and Nicole Carsten were all smiles at the party. They were excited to honor former Mayor Jim O'Brien while celebrating the new mayor, Andy Williams.
The farewell party brought together three mayors: former Mayor Gary Bruhn, former Mayor Jim O'Brien and current Mayor Andy Williams.
Jacob, Emily, Jim and Kristin O'Brien have been along for the ride of Jim O'Brien serving the town of Windermere for 15 years. Jim O'Brien said he wouldn't have been able to serve without the love and support of his family.
Bill Martini, a resident and former Windermere Town Council member, was ready to roast former Mayor Jim O'Brien.
Bill Martini, a resident and former Windermere Town Council member, put a crown and cape on former Mayor Jim O'Brien before he roasted O'Brien.
Bill Martini, a resident and former Windermere Town Council member, filled town hall will laughter during his roast of Jim O'Brien.
Jim O'Brien was laughing to the point of tears during the roast.
Attendees applauded Deputy Chief of Police Jayson Bonk and the entire Windermere Police Department for the department receiving re-accreditation.
Emily O'Brien said her father, Jim O'Brien, being on council is all she's ever known. She said a younger version of herself would have said her favorite aspect of her dad being on council was being a "little Windermere celebrity," but now, her favorite aspect is knowing how she was able to be involved with the town in a unique way, volunteering alongside him at various events.
Emily O'Brien gave her father, Jim O'Brien, a big hug after her speech in which she beamed with pride over his accomplishments and the lessons she's learned from him during his 15 years of service to the town.
Jacob O'Brien held back tears while speaking of the impact his father, Jim O'Brien, has made not only on their family but the town of Windermere.
Residents raised a glass to former Mayor Jim O'Brien.
Former Mayor Gary Bruhn said Jim O'Brien did a "pretty good job" serving as mayor.
Current Mayor Andy Williams said Jim O'Brien helped shape what the town of Windermere is today through his leadership, integrity and genuine care for the people in town.
Former Mayor Jim O'Brien was filled with mixed emotions during his farewell party. He thanked everyone for their support during his 15 years serving the town of Windermere.
Former Windermere Mayor Jim O'Brien donned a crown, red faux fur cape and a key to the town while sitting on his throne and holding onto a golden striped plunger.
After resident and former Windermere Town Council member Bill Martini made town hall fill with laughter during the roast of O'Brien, the dozens of residents in attendance of the farewell party for O'Brien Friday, March 27, listened to heartfelt speeches from former Mayor Gary Bruhn, current Mayor Andy Williams and O'Brien's family members.
O'Brien was elected to Windermere Town Council in 2011 and later won his bid for mayor in 2019. For 15 years, he has sat in Windermere Town Hall one Tuesday night per month leading the town into the future.
In January, he decided not to seek re-election for mayor as he felt he accomplished everything he wanted in his time on council and believed Windermere was in good hands with its current leadership.
"When I first stepped into the role of council person 15 years ago, I had a simple vision to keep our town a place where families can thrive, residents are safe, transparency and integrity are core values, and everyone feels they belong," O'Brien said. "Small but smart ... but that's not just my vision, that's the vision of every individual who I've had the pleasure of serving with. ... the last 15 years have never really been about politics at all. They're about service and have been some of the most rewarding of my life."
Williams said O'Brien stepped in on Town Council when the town was in need of stability, direction and focus, and he approached it with thoughtfulness, humility and a steady hand.
"Jim has always worked to strengthen the foundation of our community by working in and alongside council, with staff and residents, to truly rebuild the trust, to improve the communications and to ensure that Windermere continues moving forward in the right direction," he said. "What stands out about Jim's leadership, to me, isn't the decisions that were made over time. It was how he made them. He showed up, he listened and he treated people with respect, even when there were passionate differences of opinion."
Emily and Jacob O'Brien thanked their father for setting an example of leadership and service. They beamed with pride as they talked of their father's accomplishments and dedication to their family and the town.
