Interestingly, the candidates who did not win spent the least and the most. Retired aerospace engineer Frank Krens, who netted about 13 percent of the vote, spent a grand total of $20 on yard signs, according to his campaign finance reports. 

Jessica Lee, who works for her family’s phone-mounting accessories company, spent the most of any candidate for town council, according to the two campaign finance reports that VoxPopuli was able to examine. She spent $941.22, received in in-kind donations, for yard signs, while drawing just 9 percent of the vote. 

Windermere Mayor Jim O’Brien told VoxPopuli that town council candidates traditionally don’t spend big bucks on campaigns, choosing instead to run on their names, reputation and their love of the town. 

“Historically we try hard to not mix outside interests or funds with our campaigns and remain more focused on events and town leadership,” O’Brien said by text. “It changes politics for the better when you walk out of Town Hall with your neighbors who may not agree with you on an issue.” 

Stephen Withers, a former mayor of Berkeley Lake, Georgia, who worked as Krens’ treasurer for this election, told VoxPopuli the election was congenial. “I did not receive any negative emails, texts or calls,” he said by text. “I talked to each candidate and they were very glad we were actually having enough people wanting to serve and therefore an election. They were all concerned about getting people to vote.” 

The 2025 town council race was Windermere’s first contested election since 2021. 

Some research suggests that the more of their own money a candidate puts into their campaign, the less likely they are to win. 

It played out that way in last year’s mayoral race in Oakland, which has roughly the same population as Windermere. Like Windermere, Oakland also has a track record of infrequent elections. In 2022, the town held its first commissioners election in 16 years; last year’s mayoral race was the first in 20 years. 

During the mayoral election, Commissioner Sal Ramos, who sat on the Oakland Town Commission for nine years, sank $10,000 of his own money into his mayoral campaign. He also contributed $1,000 apiece, the maximum allowable, from his three development and construction businesses, according to campaign finance reports that VoxPopuli obtained through a public records request. 

Then Ramos raised $6,797.92 in contributions — $6,000 of which came from the family members behind the Orlando commercial construction firm Jack Jennings & Sons, The rest came from small-dollar donations. 

Overall, Ramos spent $15,596.13 on professional political consultants, campaign videos, T-shirts, large road signs and yard signs. He still won just 35 percent of the vote. 

Meanwhile, Shane Taylor, a real estate developer who chaired the town’s planning and zoning board for 13 years, seeded his campaign with $200, which covered his $105.99 qualifying fee. Then he raised $4,338, mainly in small-dollar donations from local donors, according to his campaign finance reports. He spent $1,836 on signage and flags. He won the mayor’s gavel with 65 percent of the vote.

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Norine Dworkin contributed reporting to this story.