Democratic gubernatorial candidate David Jolly addresses a town hall meeting in Naples’ South Regional Library on Oct. 13. (Photo: Author)
Oct. 19, 2025 by David Silverberg
Even in retirement-heavy Naples, Fla., it takes some kind of special magic to fill a large auditorium for a political speech on a Monday afternoon.
But David Jolly managed to do exactly that when he addressed a town hall meeting at the Collier County South Regional Library on Monday, Oct. 13.
Jolly is the Democratic candidate for governor—and if the turnout, interest and enthusiasm of the crowd was any indication, this campaign and election will certainly be intense. People are fired up—and worried.
But if Jolly is worried, he gives no indication of it.
“Believe. Believe,” he told the crowd. “My wife and I would not be in this race, I pledge to you, if we did not believe that in this moment we’ve got the best shot we’ve had in 30 years to change the direction of this state. When we change the direction of Florida, we impact national politics, we give people across the country the opportunity to look to something that’s different and better. Believe. We here believe.”
It seemed like he had the audience believing him.
It’s one thing to believe—it’s another thing to back up that belief with data, money and, ultimately, votes.
But Jolly thinks he’s got the goods.
Pure Florida
Jolly is probably as Florida as it’s possible to be for someone other than an indigenous native. He was born in on Halloween, 1972, in Dunedin and grew up in Dade City.
His father was a Baptist preacher and he was raised on Baptism’s precepts, which he has made clear still affect him as “a person of deep faith.”
It was his higher education that took him out of state, to Emory University in Georgia and George Mason University in Virginia, where he graduated with a juris doctor degree cum laude.
A Republican, Jolly joined the staff of Republican Rep. Bill Young in 1994, who at the time was representing central Florida’s 10th congressional district. Jolly rose through the various staff ranks but left the office in 2007 to work as a consultant and lobbyist. When Young died in office in 2013 at the age of 82, Jolly ran in a special election in March 2014 to succeed him, and won a narrow, 2 percent victory. He then won the general election in his own right in November without either a Republican primary challenger or a Democratic opponent.
As a representative, Jolly trended what might be called center-right, favoring what was the standard Republican litany of positions. He had campaigned to repeal the Affordable Care Act and supported overturning Roe versus Wade. In office he was in favor of tighter border controls, more restrictive vetting of immigrants and worked to maintain the prison in Guantanamo Bay.
But he also veered more centrist on other issues, arguing that regulations were appropriate to keep guns away from criminals, despite his support for the Second Amendment. He also supported the legality of same-sex marriage as part of his belief in personal liberty and opposition to government interference. At the same time, he said his Christian faith made him a believer in traditional marriage.
More particularly for Florida, he supported a ban on oil drilling in the eastern Gulf of Mexico and sought to extend the National Flood Insurance Program to cover businesses and second homes.
By the end of his term, Jolly’s approach got him ratings from The Lugar Center and the McCourt School of Public Policy at Georgetown University as Florida’s fourth most bipartisan member of Congress and the 48th most bipartisan member overall.
As the 2016 election approached, he considered a run for the US Senate seat held by Marco Rubio when Rubio was considering running for another office—but Rubio changed his mind, decided to stay in the Senate and Jolly ran again for the 13th.
This time he was opposed by former governor Charlie Crist, who had transitioned from Republican to independent to Democrat. Still a canny politician, Crist narrowly won the election by 51.9 percent to Jolly’s 48.1 percent.
Changing parties
David Jolly in repose. (Photo: Author)
There was never a single, revelatory moment when Jolly suddenly decided to switch from the Republican Party to the Democratic, he told The Paradise Progressive.
“It was more a journey. It really was,” he said. “I mean, I was a Bush 41 Republican who fought the Tea Party, right? I was an appropriator who voted to keep the government open when they wanted to shut it down. On constitutional issues like marriage equality and eventually on reproductive freedom, I was moving away. On guns, I was moving away.”
He smiles wryly: “I say Republicans didn’t want me and Democrats didn’t need me.”
And then there was the presence and over time Donald J. Trump’s domination of the Republican Party. Jolly was no Trumper. “I fought back and lost that,” he reflects.
“I knew the fight had been lost in my mind, that the party I once belonged to was never coming back and that certainly I was not a sufficient leader to try to bring it back. And I spent six years as an independent, which was the most informative part of my political life, to be untethered from a major party, major party dogma.”
It was at the time he and his second wife were expecting their first daughter that he considered leaving the Republican Party. When he did it, he did so in a very public way.
“I basically announced on Bill Maher that I was leaving,” he said of his Oct. 5, 2018 appearance on Maher’s program. “I said I wanted our kids to know, I wanted my daughter to know, that it’s important to fight for what you believe in. But there came a moment where I was accepting that I wanted her to also see sometimes there are fights you walk away from.”
Or as he put it then, “Somebody else can fight for the dignity of the Republican Party now—it’s not my fight anymore.”
Jolly went on to become a political independent and a commentator for MSNBC, where he was consistently critical of Trump.
Then, this year, after making campaign-like appearances around Florida, including an appearance and speech in Naples on May 17, Jolly announced on June 5 that he was running for governor as a Democrat.
Jolly is well aware that there are critics who question his commitment to the Democratic Party and its principles.
He himself said, “I’m in a very post-ideological space. I really am. I think the left-right spectrum confines us and restricts us.”
However, his time as an independent gave him perspective, “I just got to look at what are the big answers to our big problems?” he said.
What is more, as he said to the crowd at his town hall in Naples: “Is it okay to change your mind?” While the crowd applauded and cheered he concluded: “I actually think it is.”
David Jolly speaks outside the Collier County Courthouse on May 17 of this year. (Photo: Author)
A stark contrast
It’s hardly surprising that as a Democrat, Jolly’s positions are starkly opposite those of Donald Trump or Gov. Ron DeSantis (R) or his leading likely opponent, Rep. Byron Donalds (R-19-Fla.).
But more than partisan, his positions are aimed squarely at the concerns of everyday Floridians and away from broad, national ideological questions.
Overall affordability and the high cost of insurance are key problems to be tackled, in his view.
“The property insurance crisis is the primary reason so many people in Florida are struggling to afford a home,” notes his platform. “From renters to retirees to homeowners, the burden of property insurance continues to make housing costs in Florida unaffordable for many.” He is pledging to make alleviating that problem a key focus of his governorship.
Notably, he is pro-choice. “Reproductive healthcare decisions should be made between women and their doctors, not politicians,” states his platform. He wants Florida to codify the same rules that held during the Roe v. Wade era.
He also recognizes the reality of climate change. “Florida should accept the science of climate change, protect our beaches and state parks, and invest in resiliency throughout the state,” according to his platform.
While supporting the Second Amendment, he thinks that Floridians have suffered enough from gun violence and lax gun laws. As his platform states: “Florida should ban the sale of assault weapons, require universal and comprehensive background checks, explore licensing, and preserve and expand the red flag laws enacted following the tragedy at Parkland.”
The litany goes down the line. But most of all, he emphasizes, he’s running on a platform that transcends party dogma.
And perhaps one of his most compelling positions is his call to treat everyone with “kindness, dignity and respect.”
“Culture wars divide and demonize,” states his campaign platform. “Florida should reject the politics of division and hate, and instead create a home where everyone is valued, respected, and welcomed. We should become a place where everyone is given dignity and equity, regardless of race, creed, or color, and regardless of who you love or the God you worship. Florida should embrace our immigrant community and celebrate their contributions to our state’s culture and economy. It’s time to create a Florida for all people.”
And there’s another promise he makes when it comes to culture, as he confided to his Naples audience.
“I’ll also tell you, one of the things I want to do when we get elected governor is bring back art to the state of Florida,” he said to enthusiastic cheers. “I want to open the governor’s mansion through loan agreements with major art installations. Bring back the art that lets us see who we are, who we could be, who we’ve been. Test the boundaries, bring back culture and theater, and open it up to the people of Florida. Open it up to school kids and everyone else. Otherwise, who else wants to go to Tallahassee?”
But can he win?
Jolly is running in a state where registered Republicans outnumber Democrats by 1.4 million, where the Republican governor won by 22 points in 2022, where his likely opponent is endorsed by Trump and has $31.5 million in campaign funds.
And yet Jolly is not only confident he can win, he radiates that confidence and can convey it to a crowd.
“We’re seeing it on the ground,” he said in response to a question about his path to victory. What’s more, “we’re also seeing it in the data.” Polling backs this up, he insisted. “I feel very comfortable saying we’re in the margin of error. We have a poll that has us leading by one [percentage point]. Donalds’ [poll] has him leading by four.”
But it’s the overall political environment that fuels his certainty. “So very critically, the environment and the cycle is one of dramatic change,” he said.
Why? “It’s because people are angry, they’re worried about their economy, and they don’t trust incumbent politicians right now. And so, yes, for us, that made the decision to get in this race. I really mean this, having been involved in probably 30 races—as a candidate in only three or four—I have zero interest in chasing a generic ballot, as I say. I know there’s an opportunity for change in Florida.
“And layer into that, we have a generational affordability crisis that truly is hitting Republicans as much as it’s hitting Democrats. And so that contributes to this environment.”
He pointed out that recent special elections in Florida have swung Democratic by 15 and 16 points. It has led DeSantis to avoid special elections, for example for his appointed lieutenant governor, Jay Collins, or in counties like Palm Beach. It’s also a trend throughout the country.
“This is a race that allows an Andy Beshear to get elected in Kentucky, a race that allows Steve Bullock to get elected in Montana, and a race that allows David Jolly to get elected in the state of Florida,” he told the crowd in Naples.
But he also acknowledged that the odds present a direct challenge to him: “I have to build a campaign that can win in this moment and win in this cycle.”
That also means closing the money gap. Donalds is reporting $31.5 million in the bank. Jolly has raised $2 million.
But Jolly sees an upward trend and points out that it’s still early in the race.
“We have small dollar donors from all 50 states,” he said in our interview. “Some of the largest investors in American politics have agreed to support us. But others are just ‘wait and see,’ right? There’s no reason for them to spend money in October of ‘25.”
What’s more, the Republican fundraising advantage may not endure.
“I would also say Republicans are very likely about to have a bloodbath of a primary and spend all their money against each other. And what I’m begging Democrats is—and that’s why I said it over and over today—if I’m insufficient, make me stronger.” In other words, he wants to have the dialogue that will enable him to learn and become more effective.
He also dismisses the impact of a Trump’s endorsement of Donalds in the general election.
“With a state exhausted by MAGA, it hurts more than it helps,” he observed.
He continued: “The way I look at this race is that 33 percent of the state is probably unavailable to us. I’ll make my case as hard as I can. But if 39 percent of voters are registered as Republicans, I believe we will get 15 percent [of that].” If he can win over that percentage of Republican voters he can negate six points of likely Donalds supporters.
“So I do believe 33 percent of the state is loyally behind Donalds and Donald Trump. But in the midst of a dramatic change environment, to be able to have 67 percent of the state available to us, I feel very, very good about that.”
The possibility still exists that Jolly could face another Democratic challenger for governor. Right now he’s the only Democratic candidate and both in his speech and interview he called on his fellow Democrats not to be part of what has traditionally been called “the circular firing squad”
“Be a part of how we win,” he urged. “Don’t be a part of how you tear us down. Whether that means we have a primary or not, we’ll see. Family conversations aren’t all bad. They can be good. But we just have to remember that this is about Democrats leading a new coalition in American politics. And the only way we do that is if people look at the Democratic Party and see something they want to be a part of. If we fight each other for the next year, nobody’s going to be interested in that.”
Meanwhile, Jolly is taking a leaf from another former Democratic Florida candidate. He said his strategy is to go into communities across the state no matter their apparent ideological tendencies.
“I’m going to do what Lawton Chiles did in 1970. We’re going to go everywhere, absolutely everywhere. Deep red communities, frankly like Naples.” In 1970 Lawton Chiles, campaigning for the US Senate, did a 1,000 mile trek across Florida, visiting every community en route and talking to people along the way. He won the Senate seat and then went on to be elected governor in 1991, passing away in 1998.
Similarly, Jolly intends to visit as many communities as possible and once in those communities he intends to challenge Republicans to reveal their proposed solutions.
“Republican, what are you willing to do?’ he said. “I think we need a safe cap for insurance [i.e., ensuring that insurance can cover all contingencies]. Republicans will call it socialism. So what’s your plan? Can you convince enough people in Naples that you’re going to reduce their homeowner’s insurance, Byron? I don’t think you can. Can you convince enough people that they’re safe from school shootings? I don’t think you can, Byron. So we have to be willing to go into conservative media environments, into conservative communities and have conversations that not only express our values but ask the other side to be held accountable for their view and for their vision.”
A movement within a movement?
A demonstrator at the “No Kings” protest in Naples, Fla., on Saturday, Oct. 18, shows her support for David Jolly amidst the signs opposing Donald Trump. (Photo: Author)
There’s no doubt that Jolly projects a confidence that has been sorely lacking among Florida Democrats ever since Trump won the state in 2016 and DeSantis took the governorship in 2018. It’s a tonic for the crowds that come to hear him and it has electrified audiences, particularly in Naples.
Jolly has the experience, the objectivity and the analytical capabilities to be fully aware of the obstacles he faces, particularly in a state and a country being battered by rising authoritarianism, repression and anti-democratic tricks.
Asked if he worries about threats to the upcoming elections he acknowledges the dangers but is determined to press on.
“I still have faith, but I worry about it,” he admits. “And I worry about other areas of interference shy of Election Day.
“I worry, for instance, as a candidate, that the Trump administration is going to investigate major Democratic candidates across the country. And I worry about that on a personal level. I know there’s nothing [I’ve done] that merits an investigation. But it’s easy for what I believe is the current posture of the president to launch an investigation.”
He also worries that Trump could declare a national emergency on some pretext shortly before the election and somehow try to stop it. But he continues to campaign on the presumption that the election will be free, fair and honest.
He is also fully aware of the physical danger to candidates and public figures in the current atmosphere. After the assassination of Charlie Kirk, Jolly said that he sat down with his wife and his team and had a conversation about whether to stay in the race. But he—and they—decided the stakes were too big and the outcome too important not to keep campaigning.
He also wanted to send a message to his children. “I guess with our kids, I wanted them to know that the story I’m telling is true. I want them to know we’re trying to change the world. And that, win or lose, it’s a gift.”
Jolly has set an arduous task for himself. His is a campaign that is truly grassroots, he will be campaigning everywhere in a big state; his Naples town hall was already his 81st campaign event and the campaign is still in its early stages. He knows how intense it’s going to get as time goes on and especially in a year’s time when the race has tightened and is nearing the finish line.
But if Jolly is fazed by the prospect, he doesn’t show it. If anything it fuels his resolve.
“I know what is within our power, which is to build a coalition strong enough to win overwhelmingly,” he said emphatically. “And I know that sounds like a wild aspiration in Florida, but it’s why we’re in it. It’s why we’re in this, because if we can build a big enough coalition in Florida to overcome that, then I think that people have spoken.”
He also knows the part he must play to win and that it’s long, exhausting and potentially dangerous. “But,” he continues, “if we win, it’s because Florida’s voters have decided enough is enough—and we’re going to overwhelmingly take back the state.”
Liberty lives in light
© 2025 by David Silverberg