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With no challengers for town council, Windermere may not hold election for second consecutive year

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Norine Dworkin

Editor in Chief

Thursday, January 12, 2023


Columbia College; Town of Windermere

Local builder and reality TV show veteran Tom Stroup will likely take over the town council seat from Bill Martini who is not running for a third term. If no other candidates, besides incumbents Mandy David and Anthony Davit, file to run before noon on Friday, the town will not hold the election.

Orange County’s municipal elections are scheduled for March 14, but the town of Windermere may not hold its election for town council  — for the second consecutive year — if no challengers emerge to run against incumbents Mandy David and Anthony Davit by noon Friday when the qualifying period closes.  

Both Davit and David were elected in 2021, and both told VoxPopuli in separate emails that they are standing for re-election. Davit filed his paperwork with the town clerk Dec. 19; David filed Dec. 29.

[Candidate Mandy David Seeks 'connection' in running for Town Council]

No additional candidates have filed paperwork to run, Town Clerk Dorothy Burkhalter said in a Thursday afternoon email. Candidates are required to live in Windermere for at least 12 months before running for office. They must also collect 25 signatures certified by the Orange County Supervisor of Elections and pay a $25 filing fee.

Elected officials serve two years, and the job is unpaid.

[Retired Air Force Col. Anthony Davit turns his civil engineer's eye to solving Windermere's traffic, flooding problems]

Longtime Council Member Bill Martini — a local realtor known for his popular Otter Cam that captures the antics of a pair of Lake Down otters that routinely visit his deck — is not seeking re-election. He emailed VoxPopuli that he “will continue to stay involved with various Town committees and may consider another term some time in the future.”

Tom Stroup, who spent 31 years in the Orange County Sheriff’s Department — including 29 years as a SWAT commander — filed paperwork Jan. 3 to run for Martini’s seat. He stepped down from the Historic Preservation Board to run.

This is Stroup’s second bid for office. In 2018, he announced a run Feb. 21 for Orange County Sheriff, only to withdraw from the race 10 days later, writing on Facebook that he didn’t have the “required time to dedicate to an effective election campaign.”

Stroup told VoxPopuli Tuesday that he wished to wait until after the qualifying period to make a statement about his campaign because he had heard others may be interested in the race, and he wanted to talk with them first. Stroup, an active member in the men’s Christian fellowship group Ironmen of God and known for leading “gratitude walks” through the town, emphasized his strong commitment to the community.

Stroup owns the Windermere construction company Tom Stroup LLC, which does building renovations. He posts videos of many of his projects, like replacing support posts on Windermere’s Family Church, home how-to-fix-its and furniture crafting, on his Bob Vila-meets-Harley Pasternak YouTube series Toms Tools Tips. He has 728 subscribers.

If Stroup ends up serving on the town council, he will be the only member with his own IMDb page. The former SWAT captain appeared in the NBC reality TV show Stars Earn Stripes, hosted by Gen. Wesley Clark, in which celebrities teamed up with military and law enforcement experts to engage in military training challenges for charity. Stroup paired with actor and singer Nick Lachey. He also appeared in School Pride, another NBC reality TV show about helping communities to transform underperforming schools. Both shows ran for one season each. 

When Stroup received the 2015 Distinguished Alumni Award from Columbia College, his alma mater in Columbia, Missouri, Mark Burnett, the executive producer of Stars Earn Stripes, described Stroup as a hero and told the school he was "proud to know him." Orange County Mayor Jerry Demings, who was Orange County Sheriff at the time, said Stroup was "responsible for saving numerous lives during his career. The entire agency is extremely proud of the honor he brings to us."

If none of the candidates has an opponent, the election will be deemed "uncontested," and the qualified candidates will take seats on the council. That's what happened in 2022 when there were no challengers to Mayor Jim O’Brien or Loren “Andy” Williams. Both automatically received third two-year terms. The seat vacated by former Council Member Chris Sapp, who chose not to run for re-election in 2022, was empty until Town Manager Robert Smith asked Molly Rose — who previously served on the town council from 2010 to 2017 and then filled out another member’s term from 2017 to 2018 — to come out of retirement. Five of Windermere’s 10 elections in the past decade have been uncontested.

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