TALLAHASSEE — Fresh off a commanding reelection and a sweeping party victory, Gov. Ron DeSantis now moves full throttle into the next stage of his ambitious political career and faces a question everyone in his orbit is asking: When does he announce his run for president?
How that plays out has repercussions for both DeSantis’ future in politics and for Florida, which has never had a sitting governor seek the nation’s top job.
According to six political strategists interviewed by the Times/Herald, DeSantis is uniquely poised to seek the Republican nomination for president in 2024, even if former President Donald Trump announces he is running and puts an uncomfortable target on the governor.
Some say DeSantis is also in a good place to wait out the drama, until 2028 if needed, as Trump tries to freeze the field. Others say he has been building to this moment since he was elected to office, and must seize the momentum now.
“The bad news for Ron DeSantis is that his struggle with Donald Trump — whether they run against each other or not — is going to begin in earnest on Wednesday, because that’s what everyone is going to be talking about,” said Carlos Curbelo, a former Republican congressman from Miami who runs a public affairs consulting firm.
The governor’s decisive victory, and Trump’s eagerness to announce a campaign to complicate any federal legal investigations against him, have put an end to “this yearlong cold war” between the two men, he said.
Fueling the speculation that DeSantis is ready to run is the massive support among the Republican Party’s donor class that he has assembled. Deftly using his campaign for governor and popularity among conservatives for his COVID policies and culture war messaging, DeSantis positioned himself as the chief challenger to Trump.
“There is a reason for this,” said David Jolly, a former Republican congressman from Tampa who served with DeSantis. “There are people who have all the money in the world, and they’re going to spend it because they want to stop Donald Trump. But they need a vessel.”
DeSantis has been selling himself to the wealthy donor class as that vessel — a more policy-minded alternative to Trump who also speaks the language of the MAGA base.
With massive checks, like $10 million from hedge fund CEO and philanthropist Ken Griffin, and endorsements from people like Elon Musk, he amassed a head-spinning $200 million war chest against Democrat Charlie Crist. After the governor’s race, he is expected to have an estimated $100 million remaining that could be steered into a federal presidential campaign account.
Riding a hot streak?
For John Morgan, an Orlando attorney and a Democrat who has both commended and criticized the governor, life is a gamble and DeSantis had good luck with his decision to “roll the dice on COVID.”
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“A more prudent person would say we should be more careful, but he wasn’t, and that was a gamble,’’ Morgan said. “Luck smiled on Ron DeSantis, and he now looks like a million dollars.”
For that reason, Morgan said, DeSantis now must take on Trump.
“DeSantis is smart. He knows timing is everything because life is luck,” he said. “You’re at that craps table and you’re on a hot streak. You keep rolling. Because if your hand gets cold, it’s over.”
But if Trump announces his campaign before DeSantis is in the field, Florida’s governor will face what could be the greatest challenge of his political career. He must not only defy the person who catapulted him into office four years ago — when Trump endorsed him in the primary for governor over the front-runner then, Republican Agriculture Commissioner Adam Putnam — DeSantis must also blaze his own trail against Trump, whose playbook he has followed for four years.
“One thing Ron DeSantis has never done is directly challenge Donald Trump,” Jolly said. “He has used Donald Trump to get to Tallahassee. He perfected Trumpism in some ways, flattering Donald Trump, but he’s never challenged the former president or confronted him.”
But time is on his side, too
Al Cardenas, a former chairperson of the Republican Party of Florida who has spoken out against Trump, said the risk of DeSantis being pummeled by Trump in a primary is so high the Florida governor should be in no rush to run in 2024 — unless Trump does not stay in the race.
“Ron DeSantis is 44 years old. He’s been traveling the country, campaigning for candidates for governor and Senate and, for the first time, building up a pretty good Rolodex of IOUs — which is good for him,” Cardenas said. “Donald Trump can’t run for reelection if he wins, so if you’re 44 years old, and you’ve got a pretty good runway, why not be governor for two years and then start running for president two years from now? You’re still going to be only 47 years old.”
Running a campaign for president, unlike a state operation, “is a different ball game” and will require a different calculus, said Brett Doster, an adviser to former Govs. Jeb Bush and Mitt Romney and former President George W. Bush.
“Anyone who hits the first four states’ cocktail, picnic or barbecue circuit, they’re going to be exposed like no other state campaign will ever expose you,” Doster said.
“You live in a fish bowl and it’s not a controllable fish bowl,” he said. DeSantis has demonstrated in his campaigns that he is more comfortable giving speeches and hosting rallies than the retail politics required by intimate gatherings in coffee shops and farm fields.
“So, for anybody, that takes a lot of getting used to, and that’s why it takes people running a couple of times before they become president,” Doster said.
Rick Wilson, a former GOP political consultant and one of the founders of The Lincoln Project, which has opposed DeSantis, predicts both Trump and DeSantis will run in 2024.
“Donald Trump is going to get back in the Republican primary, probably sometime immediately after the election, and at that point, Ron DeSantis becomes the leading anti-Trump candidate in the country,” Wilson said. “And as we’ve seen over time, that is an uncomfortable place for any Republican candidate to be.”
Even before DeSantis could make it official, the former president started his pokes. At a rally in western Pennsylvania on Nov. 5, Trump affixed one of his famous derogatory nicknames to DeSantis, calling him “Ron DeSanctimonious.”
The governor had just launched a new ad in the Trump mold, using the booming voice of a narrator to send a messianic message that “God made a fighter” in DeSantis.
Leaving the polling place in Palm Beach on Tuesday, Trump threw shade on a DeSantis run. “I really believe he could hurt himself badly,” he told reporters, according to The Wall Street Journal. “I think he would be making a mistake, I think the base would not like it — I don’t think it would be good for the party.”
Trump added that if DeSantis does run, “I would tell you things about him that won’t be very flattering — I know more about him than anybody — other than, perhaps, his wife.”
Trump consistently polls ahead of DeSantis and has a loyal following among conservatives, but DeSantis is often praised by the GOP as a more disciplined politician and with a more deliberate leadership style. DeSantis also has steadfastly avoided suggesting that the 2020 election was stolen, unlike other prospective 2024 GOP candidates.
How a 2024 DeSantis navigates the tricky task of telling Trump’s base that he is just as reliable as Trump while trying to describe Trump as “damaged goods who may end up helping Democrats the way he’s done in the past” will be his ultimate test, Curbelo explained.
To distinguish himself from Trump, DeSantis will continue a strategy of relying on a compliant Republican-controlled Legislature to expand his culture war agenda, the strategists said.
“The best election strategy is a good governing strategy,” said Doster, who also represents GOP legislative and congressional candidates.
Because Florida is considered “the minor leagues for national politics,” things won’t look any different for Florida if DeSantis is under the microscope of a national campaign, Doster said.
“He just needs to keep governing well for the next six months, and if people say, ‘OK, but aren’t you running for president?’ He’s going to just maintain the same posture and say, ‘Look, we’re dealing with some big issues facing Florida right now.’”
Doster expects the governing agenda to include more school policy aimed at conservative and evangelical voters.
“I think you’re going to see aggressive action on trying to secure what I would call parental controls over curriculum and classroom instruction,” he said. Other legislative initiatives will include expansion of school tax credits for families to send children to private schools.
DeSantis also will continue to appeal to the evangelical wing of the party with policies that tighten abortion laws and gender-based policies, as well as strengthen school choice, the consultants said.
For example, incoming Senate President Kathleen Passidomo, R-Naples, said recently that if Republicans get supermajorities in the House and Senate, the governor and legislators will seek to expand into higher grades the Parental Rights in Education Act. The law, known by opponents as the “don’t say gay” act, prohibits classroom discussion of sexual orientation and gender identity issues in K-3 classrooms and in older grades if the lessons are not “age appropriate.”
And, if he’s running, the governor may also ask the Legislature to revise the state’s “resign to run” law to allow him to remain in office as governor while also attempting to qualify as the nation’s Republican nominee for president.
But the political operatives also say that DeSantis’ greatest vulnerability at home lies with Florida’s post-hurricane economy.
The governor has announced he will call a special session in December to address Florida’s property insurance market, but neither he nor the incoming leaders of the House or Senate would say before Tuesday what they have in mind. Policy options are limited, and changes adopted in a May special session have yet to have much impact on a tightening property insurance market.
If homeowners can’t obtain property insurance, they can’t get home mortgages, and a mortgage crisis could crater Florida’s budget surplus just as DeSantis is trying to sell himself to the nation, Curbelo said.
“It could become an Achilles heel, and certainly it’s something that either Donald Trump and others would try to exploit,” he said.
Looming insurance crisis
At a DeSantis campaign rally in a Sarasota airport hangar on Nov. 6, Alisha Della Volpe said that if the governor was reelected, she would like him to put his attention into fixing the property insurance market.
“Insurance is outrageous and it’s only going to get worse after the storm,” said Della Volpe, a 43-year-old Sarasota resident. “I’d love to see him fight that along with the gas prices and inflation.”
Gina Barnaba, 51, of Sarasota said top on her list of issues for the governor to tackle was both inflation and homeowners insurance. “We just want things back the way they were in 2019,” she said. “It’s getting harder every day to be an everyday American.”
But, while DeSantis used the speech to blast the Biden administration for pandemic spending policies that he said led to the nation’s inflation woes, he made no mention of the unique-to-Florida insurance crisis.
Cardenas, the Miami political consultant, said that while issues like property insurance may hurt the governor’s numbers among independents, Democrats and moderate Republicans in Florida, “for his populist and MAGA base, policy positions don’t seem that significant to them.”
“We’re probably in the worst position we’re going to be in regarding the insurance crisis, and that doesn’t seem to affect the governor’s numbers,” Cardenas said.
Now or 2023?
So if DeSantis runs in 2024, when does he announce?
Jolly argues that DeSantis can’t wait and must declare before the end of the calendar year.
“If Trump’s not in the field, you can’t fault DeSantis for getting in,” he said. “He’s got the hottest hand in politics. He has all the money in the world. He’s the clear front-runner in a Republican primary. And there’s going to be a lot of people that flirt with getting in, in the absence of Trump.”
But if he waits, and lets Trump in first, “then the story is ‘DeSantis is challenging Trump,’ and that’s a dynamic he’s never had to absorb within his political brand.”
Morgan, however, says DeSantis also has to worry about peaking too soon.
“When you get overexposed, you become overconfident and when you became overconfident, you can step on yourself,” he said, noting “that’s what happened to Howard Dean.”
The former Democratic governor from Vermont whose mercurial rise in the polls ahead of the 2004 Iowa primary led to a level of media saturation that amplified a brief gaffe and ultimately preceded his steady decline.
Curbelo said he thinks DeSantis will wait until late spring or summer.
“DeSantis is extremely disciplined, and talented, and in his mind, I’m sure that it’s probably better to have Trump go out there and maybe implode or maybe just hurt himself — the way he has done in the past — while DeSantis sits back and lines things up,” he said.
So what does DeSantis say to his onetime mentor whose supporters he wants on his team?
“Just be the nice guy,” Jolly advises. “Ron DeSantis has an opportunity to be gracious and to say, ‘I have enormous respect for the former president, and if he’s the nominee, I’m excited to support him. I also know that there are millions of Americans who have encouraged me to run, and so I’m also going to put my hat in the ring.’”
Bradenton Herald reporter Ryan Callihan contributed to this report.