- December 19, 2025
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The stage has been set for the Winter Park General Election in March, with one candidate stepping out of the race and another announcing his campaign prior to the Jan. 6 qualifying deadline.
Winter Park could be in for new faces on the City Commission, as Mayor Ken Bradley will not be running for a third term and City Commissioner Steven Leary threw in his bid for the title mayor, leaving his Commission seat empty.
Announcing his candidacy for the soon-to-be open City Commission Seat 1 last week was former city utility advisory board chairman Greg Seidel. The Winter Park resident currently works as the vice president of The Balmoral Group, an engineering design firm with an expertise in economics, environmental analysis and GIS capabilities.
“I feel I’ve been called to public service,” Seidel said. “A lot of the issues that the city is facing are issues I’m familiar with because of my background as an engineer and being on the utility advisory board.”
“I’d like to see the undergrounding [of power lines] accelerated, figure out the traffic issues in town and I’m for smart economic development … Instead of just complaining about things, I want to get involved and make them better.”
Seidel will run against former Winter Park mayor and City Commissioner Gary Brewer, the longest serving public official in the city’s history.
Brewer said he offers a balanced point of view in regards to development controversy in the city, seeing things from both the developers’ and residents’ perspectives.
“I recognize the balance – you can’t overdevelop due to issues of traffic, and environment issues have to be considered,” he said. “It’s a delicate balance. I think I appeal to both sides of that issue.”
Candidate Willow Shambeck meanwhile announced she would be stepping down this week and would not be running for the open City Commission seat.
She cited financial concerns with supporting her campaign as her reason for stepping aside.
“Due to recent events in the Winter Park City Commission election and recent developments in my business, I have decided it is better to withdraw my candidacy for Winter Park City Commissioner,” Shambeck said in a released statement. “With the addition of a third candidate, the race will require nearly 100 percent of my time and resources to run a February Primary Election and a March General Election. The two short but equally intense election cycles would require nearly 24/7 attention and double the fundraising, which I unfortunately cannot afford to dedicate at this stage in my business.”
Shambeck has also endorsed Leary for mayor and Brewer the open Commission seat.
City Commissioner Steven Leary said he hopes to continue what he’s started if he takes up the mantle as mayor of Winter Park, supporting the replanting of trees, looking to improve Winter Park’s business corridors and holding the line on the city’s reserve fund.
It’s his four years on the City Commission and wealth of experience in business that, he said, make him the right man for the job.
“I think it’s important for a mayor to have business experience,” Leary said. “You need to understand how to work with others to get results. It’s about giving everybody a seat at the table.”
“You need to be involved with the city to understand how it works. Mayor is not on-the-job training, I believe it’s citizen leadership.”
Running against Leary for Winter Park mayor is Cindy Mackinnon, a retired Florida Circuit Court Judge.
Mackinnon, a Winter Park resident for 46 years, said she hopes to bring stability and security to a city she believes is being eaten away at by encroaching development.
“I don’t want to let developers exploit the paradise that we have here,” Mackinnon told the Observer in November. “I want development that’s in keeping with the character of our town.”
“I’m running because I feel like we’ve reached a tipping point in our city. We’re in danger of becoming just like any other city in any state in America. We have something unique here, which we have to preserve.”
The general election will take place on March 10.