David Jolly is running for governor of the reddest areas of an increasingly red Florida

NAPLES, Florida – David Jolly’s long-term plan to win the keys to the governor’s mansion is based on a basic premise: that after seven years of Governor Ron DeSantis and the return of President Donald Trump, Floridians have had it.

“I wouldn’t be in this race, I promise you, if we didn’t believe that right now we have the best opportunity we’ve had in 30 years to change the direction of the state,” he told more than 200 attendees who packed a meeting room at the Collier County Southern Regional Library on Monday.

“This is a moment when Florida voters say, ‘We’ve had enough,’” he had told 400 Lee County Democrats in Fort Myers a day earlier.

Whether the recent Democratic convert and former Republican lawmaker’s analysis is correct won’t be known for a year, when voters choose a successor to the term-limited DeSantis. Until then, Jolly, who currently has no known Democratic opponent for the nomination, said he plans to campaign for votes in all 67 Florida counties, a strategy that has largely fallen out of favor among Democrats since the 1980s, when they had almost complete control of state government.

“We’ve done 94 events across the state since I started running for governor. Ninety-four,” he said at a welcome session on Marco Island Monday night that drew another 50 or so people. “I leave everything on the field.”

Naples and Marco Island were the last two of a half-dozen events he held over Columbus Day weekend in one of the most Republican corners of an increasingly Republican state: Southwest Florida, counties that haven’t voted Democratic in decades. Naples, the site of his visit Monday afternoon, is the home of Republican lawmaker Byron Donalds, who with Trump’s backing is likely to win the Republican nomination next August.

“We’re in Naples, in deep red Collier County, and look at this turnout,” Jolly, 52, exulted as he took the stage, later acknowledging the area’s reputation as a haven for retirees. “It’s great to be the youngest person in the room!”

Perhaps to set expectations low, Jolly explained early on that he is not a “viral” candidate and promised not to delve too deeply into political discussions, then delivered a 45-minute speech that seemed to keep his audience interested throughout.

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While Jolly followed the conventional wisdom that voters are more interested in pocketbook issues (“This is a state hit by an affordability crisis”), he also spoke with ease about issues that many consultants advise Democrats to avoid.

“We are home to culture wars that are giving people reason to stop and ask themselves if Florida is a place where they feel welcome, if their grandchildren or children feel welcome, if their Canadian friends want to visit them,” he said Monday. “And what my Republican friends have never realized is that culture wars have victims.”

Jolly, who is white, straight, married and has young children, also defended DEI goals that have been vilified by both Trump and, at the state level, DeSantis.

“It’s not an attack on meritocracy to lift everyone up. It’s an enhancement of meritocracy to do that. We should welcome everyone, and it’s okay to embrace diversity in this state,” he said.

Only at the end of his remarks, which he delivered without notes, did Jolly even mention Trump, who last November won Collier County by a 66-33 margin over Democrat Kamala Harris. “Many of you in this room (you can look left and right) have Googled Portugal,” he said, referring to the tendency of Americans to seek refuge from Trump’s increasingly autocratic dictates.

He noted that he was the only Republican member of Congress to call on Trump to drop out of the presidential race after he promised to ban Muslims when he ran in 2016. “I risked my job as a Republican to take on Donald Trump. I did it,” he said.

However, he urged those inclined to support him to avoid even mentioning Trump to their Republican and independent friends and instead focus on the race for governor.

“This is a race that allows Andy Beshear to be elected in Kentucky, a race that allows Steve Bullock to be elected in Montana and a race that allows David Jolly to be elected in the state of Florida,” he said.

“It’s not an attack on meritocracy to encourage everyone. It’s an enhancement of meritocracy to do that. We should welcome everyone, and it’s okay to embrace diversity in this state.”

– David Jolly

Jolly, although clearly speaking mainly to people who were already willing to support him, seemed to make a favorable impression.

“He communicates well. He doesn’t exaggerate. He admits what he doesn’t know. He talks about trying to figure out where we are together and what we agree on, rather than why we are different,” Michael Finkel, a 78-year-old retired doctor, said after the visit to Naples. “Quite refreshing.”

Retired sailboat Carol Beers was in the audience the previous afternoon, when Jolly was the keynote speaker at a fundraising luncheon for the Lee County Democratic Party in Fort Myers. She said it was the first time she had heard it in person and she was impressed. “People loved him,” he said.

Can that love from longtime party activists translate into winning a state where the other party now has a 1.4 million registration lead? On that point, Beers, 73, admits she’s not sure. “If he can’t do it, no one can.”

Democrats have not won a gubernatorial race in Florida since 1994, when Lawton Chiles narrowly defeated Jeb Bush. When President George HW Bush’s second son ran again four years later and won, it was the start of a streak that now spans seven elections.

What’s more, Democrats have only come close twice in those 24 years. If there’s a glimmer of hope for Democrats in that record, it might be Republican-turned-Democrat Charlie Crist’s near-victory in 2014 against incumbent Republican Rick Scott.

Crist, like Jolly, is also from Pinellas County in the Tampa Bay region and, like Jolly now, ran as a centrist Democrat. Crist, however, had the advantage of five previous statewide runs, including a term in the governor’s mansion from 2007 to 2011 as a moderate Republican.

Jolly had never run a statewide race before, which in Florida is a daunting task due to its large size and 10 different media markets. Candidates must raise and spend tens of millions of dollars to reach the roughly 10 million likely voters.

To date, Jolly has raised around $2 million. Republican Donalds has raised more than 15 times that amount so far, although Jolly’s staff said Democratic money will likely flow if the race looks winnable by next summer.