Candidate Profile: Tom Stroup

“Those who can, must.” 

As creeds go, that’s a pretty good one for public service. Particularly as you make the case that you’re the one who must serve the public. 

In an interview with VoxPopuli, at Windermere’s chic coffee cafe Paloma’s on Main Street, Council Member Tom Stroup, 67, is talking about the sense of civic responsibility that first pushed him in 2023 to run for town council.

At the time, Bill Martini, a realtor, was stepping down, having served four years on the council; a seat was open. After attending council meetings for years as a resident, Stroup, who’s lived in Windermere with his family since 1999, said it was time for him to do his part. 

“ I just figured it was my civic duty, you know. Instead of just sitting in the audience and raising my hand with an opinion, get involved in the decision-making process,” said Stroup, who is now running for his second term. 

“I was not unhappy with the decisions made [by the council] in the past,” he said. “I just feel like it’s my duty to be involved. It should be a duty for anybody who can. If not me, who?”

That is not really a rhetorical question. Windermere has not exactly seen a parade of candidates beating a path to the town clerk’s door to serve on the council. Five of Windermere’s last 10 elections ended up canceled when candidates faced no opposition. The last time the town held a contested election was in 2021. Stroup himself was automatically seated when he ran in 2023.

This year, however, Windermere’s March 11 election is a horse race as five candidates jockey for three seats on the council. Stroup faces fellow incumbent Council Members Anthony Davit and Mandy David, both elected in 2021 and running for their third terms, and first-time candidates Frank Krens and Jessica Lee. Council positions are unpaid and members serve two-year terms. 

The last day to register to vote in the municipal elections is Feb. 10. Early voting takes place March 3 to 7, daily, from 8 a.m. to 5 p.m. at the Supervisor of Elections Office (SOE) at 119 Kaley Street in Orlando. Mail-in ballot requests expire at the end of 2024, so if you vote by mail, you’ll need to put in your request again. Feb. 27 is the last day to request a mail-in ballot for the municipal election, and it should be returned to the SOE by 5 p.m. on March 11 to be counted. (Ballot requests made for this election will remain active through the next general election.) ‍

A life-changing encounter

Stroup mused that “almost all of my life was a little bit of a surprise to me.”

Raised by a single mom, Stroup had dropped out of high school in the 11th grade and was married with a child in Kentucky by age 18, working in a rock quarry and picking tobacco, when a chance encounter with a farmer changed his life. He told him the police department was hiring.

“ I cut my hair, got my GED [General Education Development degree], got hired,” he said. Stroup eventually found his way to the Orange County Sheriff’s Office. He spent 32 years there, 29 as a SWAT commander, retiring in 2013. 

Along the way, he earned his bachelor’s degree from Columbia College, a small Christian school in Missouri, then a master’s degree in criminal justice from the University of Central Florida. He picked up some championships at international SWAT competitions and a gold medal in the “Toughest Cop Alive” competition. He also worked on two NBC reality TV shows, each of which ran for one season: School Pride (2010), in which struggling community schools were renovated; and Stars Earn Stripes (2012), created by Dick Wolf and Mark Burnett and hosted by Gen. Wesley Clark, which paired celebrities with military and law enforcement for training exercises to earn charity bucks. Stroup was teamed with Nick Lachey.  

In 2018, Stroup briefly entertained a run for sheriff but halted his campaign after 10 days, deciding it wasn’t the right time. He’s noncommittal about whether he’ll still seek higher office. The Orange County Commission is adding two commissioners in 2026, but it’s not yet known where the new districts will be.  

“ I'm a Christian man, and I do seek God's purpose in life, and I found that sometimes my plans are not God's plans. And I try to be available to whatever God's plans are,” Stroup said. “ I can't sit here and say that I have no interest in future political positions, but at this point in my life I have no plans for future political positions.”

A delicate balance

Stroup later parlayed his ease in front of the camera together with his building renovation skills and love of power fitness into the YouTube series Toms Tools Tips, sharing fitness ideas and videos of the many of the projects — for example, bunk beds for the annual Windermere Police department charity drive — that his construction company took on around town before he retired. He even expanded Paloma’s from a tiny shop barely big enough to order coffee at the counter to the spacious cafe it is now. 

And this raises the perennial discussion in Windermere: the push-pull between preserving Windermere and growing Windermere. 

Stroup said he understands the delicate balance Windermere needs to strike to preserve the town character — the dirt roads, the old-growth tree canopy, the Old Florida-style homes — while encouraging growth. 

“Growth is inevitable,” he said. He’s “excited” about the new construction on Sixth Ave. and Main Street. 

“We have a very limited footprint for our business community so we can’t grow a lot,” he said. “The growth I’ve seen, I’m happy with.” He mentioned that he has plans to hit the boutique Ace Hardware when it opens and visit the bakery. “I attend all the events downtown. I go to the food trucks. I go to the farmers markets … I think we’re going in the right direction.”

Annexation is another way to grow. In the Feb. 4 mail ballot referendum, 75 percent of voting homeowners in the bordering neighborhood, Chaine du Lac, which has 51 custom homes, many of which front Lake Butler, and average $3.7 million in property value, chose to join Windermere.

Some residents grumbled about annexed residents “diluting the vote” if they joined the town, according to town records. Stroup said he supported the annexation, characterizing it as a “good fit.” But he added that he would have liked the referendum opened to Windermere’s residents too.

“I wanted the town to vote on it, and I made that very clear, very clear,” he said. “I feel like all annexations should go to referendum, and that's just a general philosophy of mine when it comes to the people having an opinion about certain issues.”

An advocate for residents

In the last few years, the council has navigated several contentious issues: a legal battle with seven residents over ownership of five historic boathouses; how to design and whether to even build a $1 million events pavilion; Town Hall renovations; and a request for a variance to allow alcohol to be sold at an upscale wine market-tasting room going into the new 500 Block development. 

When it came to the variance, Stroup heard residents’ protests about too many downtown businesses selling alcohol. Although state law will still allow the new wine market to provide wine samples to patrons when it opens, even if it can’t sell wine by the glass, Stroup, who voted with the majority, denied the variance. 

Likewise, he heard the protests about the Healthy West Orange/Rotary Pavilion, which residents feared would bring visitors to Windermere for events, creating noise and trash and exacerbating the town’s traffic and parking problems. He said he couldn't support the pavilion given those concerns. 

“If you choose to be involved in Windermere, your voice will be heard,” said Stroup, who served on the Historic Preservation Board, before stepping down to run for the council. He now serves as liaison to the Windermere Police Department and to the Long Range Planning Committee and the Elders Committee. 

“Most of the time, if you’re willing to have a discussion about it, the situation gets resolved. I think the town is very receptive to the community’s needs,” he said.

“Every time I've seen an issue in Windermere that has created any sort of difference of opinions, the process has worked. Not everybody gets exactly what they want every time, but everybody's heard. And I've seen it over and over and over again.”

One issue yet to be resolved is the ongoing legal wrangling over the historic boathouses in the lagoon at Palmer Park. Although the tug-of-war dates to the mid-1980s, the current legal battle centers on the town council’s March 2022 decision to terminate the boathouse owner’s right-of-access leases.

The town council has steadily increased its legal budget to litigate the matter. In fiscal year 2022-2023, the town council budgeted $85,000 for legal services but spent $138,227. For fiscal year 2023-2024, however, the town budgeted $100,000 and spent $314,830. For the current fiscal year, which began Oct. 1, the budget is $225,000. Since the matter couldn’t be resolved through mediation, a non-jury trial is scheduled for August. 

Stroup wouldn’t answer any questions about the boathouses because of pending litigation. He also didn’t answer an emailed, follow-up question about whether this was good stewardship of taxpayer money when the council had just raised the millage rate by 7.20 percent. 

When asked about his proudest achievement in his first term, he became a bit philosophical, saying that something that he didn’t think was that important could have been very important to someone else. So he said simply, “ I hope my legacy is that the decisions that I've helped make  benefited the people that were affected the most.”