Mission Improbable: A onetime Republican is trying to prove Democrats can win in Florida

LEESBURG, Fla. (AP) — Cyn Doyle is a self-described political cynic. So when David Jolly, the Republican-turned-independent who is now running for Florida governor as a Democrat, swung through this town dotted by lakes and Spanish moss, she had doubts.

“How can you assure us,” the 71-year-old pressed, “that you won’t become another John Fetterman?”

As the crowd in the clubhouse of a manufactured home community for seniors jeered the mention of the contrarian Pennsylvania Democratic senator, Jolly, who once critiqued politicians as an MSNBC pundit, made the case for himself.

“Change is part of my journey,” he responded. “What I can tell you is that the values I speak of — that the economy should work, that government can do a little bit to improve our lives and that everyone should have the right to be protected — those are the guideposts for how I’ll serve as governor.”

Doyle, an independent who said she’s a registered Democrat mostly to participate in primaries, left impressed.

“I believe him,” she said. “I don’t believe many.”

Florida spent a generation as America’s prized political battleground, where the interests of big cities, agricultural towns, freshly arrived retirees and diverse Latino communities collided in elections often decided by fractions of a percentage point.

Jolly is bent on proving those days aren’t over.

In the course of a single day last weekend, he rallied a chandeliered ballroom in The Villages, a wealthy Republican-leaning retirement community. Then it was off to the fluorescent lights of the Leesburg clubhouse before ending with a rousing speech to Democrats in Hillsborough County, home to Tampa, which backed a Republican presidential candidate for the first time in 20 years in 2024.

Democrats have collapsed in Florida

President Donald Trump’s rise has coincided with a Democratic collapse in Florida. He won here three times, with ever-expanding margins. The 19-percentage-point win by Republican Gov. Ron DeSantis in 2022 cemented a GOP supermajority in the legislature.

Jolly’s path to victory could be blocked by both math and money in his likely race against Rep. Byron Donalds, the Trump-backed candidate in Tuesday’s Republican primary. Donalds, who would be Florida’s first Black governor, has raised more than $100 million compared to Jolly’s $10 million.

Donalds has cast Jolly as an out-of-touch liberal, blanketing the state this week with an ad featuring Jolly referring to “gender-affirming care” and backing communities painting rainbow crosswalks to show support for LGBTQ people. Jolly countered that Donalds is ignoring pressing economic issues.

In an interview over an Outback Steakhouse lunch while his wife and two young children busied themselves with coloring, Jolly acknowledged “there’s not going to be the political will” to reverse the state’s ban on transgender girls and women participating on female teams at public schools and universities.

He said he didn’t think governors should decide who plays in what sports even as he described himself as a “girl dad” and noted “I don’t think we should have biologically born men playing in competitive sports.”

“But look,” he added, “if a 10- or 12-year-old soccer league in the community has a coed team, I don’t think the governor should be throwing a flag on the field.”

Republicans face tests of their own

For all the headwinds confronting Jolly, Republicans may encounter their own turbulence.

The culture wars that have raged under DeSantis, including a feud with Disney and fights over gender and sexual orientation, have left some exhausted. Karen Kuhn, a 72-year-old resident at The Villages, described herself as in “despair.”

Democrats have won a string of special elections from Miami to Palm Beach and Tampa, adding to their optimism. Former GOP Rep. Carlos Curbelo said Latinos who voted for Trump in 2024 might not support Republicans again, in part because of the administration’s immigration enforcement tactics.

“I definitely can see a scenario where it’s a closer race, where it’s a competitive race,” said Curbelo, who narrowly lost his reelection bid in 2018, the last wave election year for Democrats.

A race with implications for 2028

Jolly is telling that to any Democrat who will listen, including those with potential presidential ambitions such as Govs. JB Pritzker of Illinois, Gavin Newsom of California, Andy Beshear of Kentucky and former Transportation Secretary Pete Buttigieg. If Florida can change, he argues, the national political landscape would change with it.

“All of a sudden the road to the White House looks dramatically different,” Jolly said. “It reshapes the House of Representatives. The structural change from winning Florida is a generational opportunity for Democrats.”

It’s a point echoed by other Democrats, including state Rep. Emily Gregory, who flipped the Palm Beach district home to Trump’s Mar-a-Lago.

“To abandon Florida was deeply, deeply unwise,” she said. “I hope that investment is coming back because it is a purple state and I feel very confident going into November.”

Nikki Fried, the Florida Democratic Party chair, acknowledged “the bottom fell out” for Democrats. She has spent the past several years rebuilding the operation. Democrats charged with winning back state legislative and congressional seats are prioritizing some Florida races this year.

But Beshear, who chairs the Democratic Governors Association, isn’t making a financial commitment yet.

“David’s working really hard,” he said in an interview. “He’s a good candidate, and we’re watching it closely.”

Donalds’ campaign remains confident. His communications director, Gates McGavick, said: “Florida voters will reject radical liberal David Jolly because he will make life more expensive.”

A ‘Bush 41’ Republican’s path to becoming a Democrat

Jolly is an unlikely figure cajoling Democrats to think about their future.

He first gained national attention in 2014 as the GOP winner of a Tampa Bay congressional seat that was seen as a bellwether. In a Democratic Party that emphasizes diversity, Jolly regularly refers to himself as a “53-year-old white former Republican with salt-and-pepper hair.” His time in Congress runs counter to voters elevating fresher voices this year.

During stump speeches, he says he was a “Bush 41” Republican. He left the GOP in 2018, spending several years as an independent before registering as a Democrat in 2025.

Orange County Mayor Jerry Demings, who challenged Jolly until suspending his campaign in June and announcing he had prostate cancer, acknowledged Florida Democrats have to appeal to independents. But he also said “people don’t want a chameleon.”

“That’s the big challenge that he’s had, is convincing people that he has stepped away from the Republican policies,” Demings said.

Others were more forgiving.

Sylvia Rieger, a 70-year-old resident at The Villages, said Jolly’s evolution showed “moxie.”

Steven Slyter, an 81-year-old retired handwriting expert, said it was “courageous” for Jolly to leave his party. “He made a decision about what he stands for,” Slyter said. “I like that.”

Florida’s last Democratic candidate for governor, Charlie Crist, was also a former Republican. After his drubbing by DeSantis, several Democrats said Jolly was campaigning more effectively.

Facing minimal primary competition, Jolly has largely avoided debates over the party’s ideological future. He’s won support from progressives including Rep. Maxwell Frost while shoring up his centrist credentials by picking former Rep. Gwen Graham, the daughter of longtime Sen. Bob Graham, as his running mate.

Some Jolly supporters are hoping that his poly-party background will be an asset.

Jeff Adelman is running for a nonpartisan seat on the Coral Springs City Commission in Broward County. As he left a recent meeting of the Coral Springs Parkland Democratic Club, he described Jolly as a potentially unique fit for the state.

“We live in Florida,” he said. “I don’t think you’re going to get somebody like Bernie Sanders to run for governor in the state of Florida.”