And it still is. The latest voter registration numbers for Sumter County, where The Villages is primarily located, show Democrats outnumbered three to one. In the 2020 election, Trump took 68 percent of the county’s votes.
But on Saturday, the Trump-loving town saw a turnout for a Harris rally that shocked organizers and paradegoers alike. It probably marked the largest golf cart caravan for a Democratic candidate in nearly a decade, said Dennis Foley, vice president of the Villages Democratic Club, which helped throw the event. The club expected to see around 250 people, but the attendance was at least double that. The unexpected show of support drew millions of views online.
President Biden’s exit from the race and swift endorsement of Harris stoked a fire in the community, where Democrats are often tight-lipped about their affiliation.
“There’s enthusiasm for Kamala and also a sense of significance to this election and that there’s a lot at stake,” Foley said. “So the combination, I think, has boosted everyone that was a little bit depressed.”
The rally was followed by a quick counter from Trump supporters in The Villages.
On Sunday, the Villages MAGA Club — which markets itself as a group for residents who “support the America first agenda to protect and preserve our great nation” — announced it would host a golf cart caravan to support the Trump-Vance ticket.
The club said in a Facebook post on Monday that the local sheriff’s office would attend the rally, writing: “We will kick out anyone who causes trouble. It’s what we expect from the democrats.”
H. Gary Morse, a Republican Party megadonor, developed The Villages into a routine stop for GOP political figures, including Trump and Gov. Ron DeSantis. After Florida flipped from a battleground to a Republican bastion, The Villages made national headlines for contentious rallies in support of the then-president.
Going into the 2024 presidential race, the Republican side of the aisle remains “very firm” in The Villages, Foley said.
“There’s nothing we can say or do that will convince them,” he said.
The shift has been within the community’s Democrats, who are starting to make an appearance larger and louder than those of the past two election cycles, when the energy of the GOP faithful dominated the town.
“I think it’s just such a stronghold here that people don’t come out to speak up and say, ‘Hey, you know, I’m voting for someone other than Trump.’ And so this was an opportunity,” said resident Diane Ruggiero.
Ruggiero, a registered Republican, said she has never voted for Trump, but she sees reminders of her neighbors’ support for him every day in The Villages. Trump 2024 flags hang in front yards, and bumper stickers are slapped on golf carts, the main mode of transportation in the community.
When she saw information about the rally for Harris on a local news site Saturday morning, she wanted to attend to support Harris’s candidacy.
Hours later, Ruggiero; her husband, Jim Guy; and their dog, Skipper were driving in the parade, their golf cart adorned with a white “Harris for President” poster. Ruggiero wore a “Dog Mama for Kamala” pin that she’d been given at the rally. Others held handmade signs that read “I’m a cat lady,” a reference to comments made by Sen. JD Vance (R-Ohio), Trump’s running mate when he derided Harris and other prominent Democrats as “childless cat ladies” in 2021. A few wore orange jumpsuits, alluding to Trump being found guilty in May on 34 counts of falsifying business records to conceal a hush money payment in 2016.
As the golf carts made their way around the town square in The Villages, they were met with about a dozen Trump supporters who stood in a counterprotest, holding signs supporting Trump.
Among them were Tommy and Valerie Jamieson, who started The Villages MAGA Club together in 2022.
The couple said they’d read about the rally online and had already been in the area of the parade route for one of their own events. During the Harris rally, Tommy Jamieson said they stood peacefully with their signs.
“This was kind of like, ‘Okay, what in the world is going on?’” he said. “Democrats having a golf cart rally, it’s just come out of nowhere.”
After the rally, Jamieson said the club was “swamped” with calls to hold a rally supporting Trump, which they’ve scheduled for Saturday, adding that he expected it to be “one of the biggest rallies ever held here in The Villages.”
The back-and-forth rallies reflect a political divide that seems poised to become more pronounced in The Villages as its Democrats come out of the woodwork, re-energized by Harris’s entry to the race.
“We are fired up to fight off the Trump-Vance ticket,” Foley said.
The way Ruggiero sees it, Harris’s candidacy has given once-quiet left-leaners in The Villages new momentum.
“I could see that energy that now people are like ‘Oh, I’m not one out of 100. I might be one out of 10, maybe two out of 10,” she said.
