“In Florida we are in the midst of a generational affordability crisis,” he added. “Everybody feels it. I mean this has been affirmed everywhere I’ve gone, every group I’ve sat with. The affordability crisis is number one on the minds of every Floridian. Wherever you live, whatever your socioeconomic status – whatever your party registration – the affordability crisis is number one. I would make the case that Republicans in Tallahassee have contributed to it, and will continue it. They won’t do anything about it, and we will. I will.”
The 52-year-old Pinellas County resident is the first major Democratic candidate to enter the race for governor in a seat that will be vacated next year by a term-limited Ron DeSantis. It’s been quite the evolution for man who previously described himself as a “George H.W. Bush Republican” for much of his adult life before leaving the GOP in 2018 to become a political independent, and then only officially joining the Democratic Party six weeks ago.
Florida hasn’t had a Democrat occupying the governor’s mansion in Tallahassee since Buddy MacKay finished out Lawton Chiles’ second term in office in January of 1999. Since then there has been eight years of Jeb Bush, four years with (then Republican) Charlie Crist, eight years with Rick Scott, and so far nearly six-and-a-half years of the DeSantis revolution.
Jolly’s previous elected experience in office is limited – he defeated Democrat Alex Sink in a special congressional election in early 2014 following the death of venerable Republican lawmaker C.W. Bill Young. After coasting to re-election that fall, Florida’s 13th Congressional District was redrawn and became friendlier for a Democratic pick-up, which is what happened when Crist defeated him in the fall of 2016.
Jolly was an early member of the GOP “Never Trumper” caucus, and his critiques of Donald Trump in his first term in the White House catapulted him into a political analysis spot for MSNBC (his contact has been paused since he began exploring a gubernatorial run, an MSNBC source told the Phoenix in April).
The independent spirit
Jolly officially left the GOP in 2018 and became a political independent, where he actively worked on efforts to provide an alternative to the two-party political system. First with the Serve America Movement (SAM) in 2021 where he served as the executive chairman, and then later with Andrew Yang and Christine Todd Whitman with the Forward Party in 2022.
It was during his period with SAM that he actively discussed the possibility four years ago as running as a political independent candidate for governor in Florida for 2022, but ultimately decided not to.
Currently the Republican front-runner for the GOP nomination for governor next year is U.S. Rep. Byron Donalds. But there’s also likely to be at least one independent candidate in the race with state Sen. Jason Pizzo saying he’s likely to join the campaign for governor this fall.
“We won’t know who qualifies for the governor’s race until next June, and that’s very important,” Jolly says. “Because our job between now and next June is to build a campaign that appeals to independents. As you know I helped mobilize the independent space for six years, and I would beg the parties that we are available to you. Speak to us, reach us, don’t ignore us. Don’t slap us down. And so Jason Pizzo’s right that the independent voter has been ignored by the major parties for too long. The answer to that is not to argue with Jason, it’s to build the Democratic Party that reaches out to independents. And if I do that, then we’ll build a coalition that Jason Pizzo or John Morgan can look at and say,’Wow. I like what I see over there.’”
The Trump Factor
Jolly’s opposition to Trump has been a central part of his brand over the years, but he tells the Phoenix that the 2026 election is about the people of Florida, not the current president of the United States.
“I believe the president has taken us in the wrong direction, just as I believe Gov. DeSantis has, but this race is not about Donald Trump,” he says. “Not for one moment is this race about Donald Trump. This race is about the affordability crisis in the state of Florida. Republicans will try to make this race about Donald Trump. They will try to make it about division, not unity. My job every day on behalf of this coalition, is to keep us focused on the affordability crisis. Investing in public schools. Providing for safe communities. Restoring dignity to people across the state of Florida. This is an open seat governorship race. I stand by my view of the president, but this race is not about the president.”
While the Florida Legislature is currently working overtime to get a budget passed, GOP lawmakers and Gov. DeSantis have talked about delivering property tax relief to Florida homeowners, most likely via a constitutional amendment that the voters would have to approve in the fall of next year. Jolly says his biggest concern about the discussion in Tallahassee on the issue so far is that the GOP has “no plan for where the revenue comes from to provide for safe communities and good schools, and they just want to chase the property tax cuts.”
He says the state needs to look at a “broad based property tax reform package” that maintains the Save Our Homes amendment that limits annual property tax increases to 3% while also providing “dramatic relief” for first-time home buyers.
University of North Florida political science professor Michael Binder says that the obvious parallel in assessing Jolly’s candidacy is with Crist, who left the Republican Party to become an independent during his last year as governor in 2010, ultimately losing a Senate bid to Marco Rubio. He officially became a Democrat in 2012 and lost two bids for governor: In 2014 by one point to Rick Scott, and in 2022 to DeSantis by 19 points (in between he served in what had been Jolly’s congressional seat for six years).
“Charlie Crist was unable to connect with base Democrats and get them to the polls,” Binder says of the 2022 contest. “If Jolly can do that, and that’s going to be a challenge being a former Republican, then maybe you might have a race that was closer. You might get a race that’s in the single digits. But if this is a similar circumstance where Democrats are not motivated, if Jolly cannot connect with the base of the Democratic Party, then there’s absolutely no chance.”
Binder adds that Pizzo’s likely entry as an independent means that both he and Jolly would be taking up what he calls a “moderate, non-MAGA type with maybe some Republican leanings” that are occupying the same ideological lane.
So far, the Florida GOP doesn’t seem too concerned.
“David Jolly has lost before, and he will lose again,” said Republican Party of Florida Chairman Evan Power in a statement issued earlier this week. “Floridians won’t trust a slick opportunist who simply can’t be trusted. Jolly has no platform, no base, and no chance in Florida.”
Jolly says while Trump’s actions in the White House will dominate the news headlines over the next year and-a-half, his campaign will be about making Florida better for everyone.
“It’s about responsibly delivering government and providing for safe communities and good schools and a property insurance and property tax construct that actually works … If that’s what we’re talking about for the next 16 months? Then we become a coalition for change and Republicans are offering more of the same, and we win the race.”
