How Ron DeSantis became a presidential candidate and what could happen next

DeSantis has shown he can raise lots of campaign cash. But Trump has more experience under the national microscope.
The question now becomes whether Gov. Ron DeSantis can keep rising all the way to the top, even when the path cuts past the man who made his political career.
The question now becomes whether Gov. Ron DeSantis can keep rising all the way to the top, even when the path cuts past the man who made his political career. [ IVY CEBALLO | Times ]
Published May 24, 2023|Updated May 25, 2023

Just a little over four years ago, Ron DeSantis took the reins of the nation’s third-largest state as a fresh-faced, young governor with no executive experience who benefited heavily from Florida’s embrace of Donald Trump. His razor-thin win came after a campaign that, in its early stages, drew only a few dozen people for in-person rallies.

On Wednesday, DeSantis filed paperwork to officially become a candidate for president, a sign of just how far he has ascended onto the national stage in a short period of time. He announced his run later in the evening on Twitter with Elon Musk.

The question now becomes whether he can keep rising all the way to the top, even when the path cuts past the man who made his political career. It’s a storyline that could have been concocted by Hollywood, yet has very real implications for the people of Florida and beyond.

The contest will be a test of whether Republicans are ready to look to the man who has branded himself as Trump’s successor — measuring how much control the former president still has over the populist MAGA movement he created.

“Are Republicans finally going to decide, ‘We need to move on and try something new?’ That means more than any issue anybody can raise right now,” said Brad Coker, a longtime Jacksonville political pollster. “Are they going to hunker in with Trump and go one more time up the hill? Or say … ‘Maybe we need a new general.’”

How DeSantis got here

So far, polling suggests the 2024 Republican primary is Trump’s to lose. The RealClear Politics average of multiple polls in the past month shows Trump more than 30 percentage points ahead of DeSantis. But this won’t be DeSantis’ first time with an underdog campaign.

His presidential announcement marks an inflection point in a complex political journey for DeSantis, during which he’s been a bomb-thrower in Congress involved in government shutdowns and a pragmatic governor, who early in his term championed bipartisan issues like smokable medical marijuana and cleaning up Florida’s waterways.

Then came the COVID-19 pandemic, a high-pressure, high-stakes environment that hardened his convictions that the news media was against him and prompted DeSantis to seize on many conservatives’ increasingly bitter distrust of experts in health care, the federal government and academia — institutions that DeSantis has said need anti-“woke” reforms, along with private corporations.

“He’s been very good at reading the political tea leaves,” Coker said.

Critics see it a little differently.

“Wayne Gretzky used to say, ‘I’m not skating to the puck, I’m skating to where the puck is going.’ That’s exactly what DeSantis is doing,” said David Jolly, a former Republican member of Congress who served with DeSantis and is now a political commentator. “Ideology doesn’t matter as long as (he’s) enacting policies the culturally conservative movement wants.”

DeSantis, the former co-founder of the House Freedom Caucus — which made the ballooning size of the federal deficit one of its central rallying cries — now says that small-government conservatism alone isn’t enough. Out of the pandemic, DeSantis has spearheaded a new Republican model where government must aggressively counter leftward cultural shifts, with particular emphasis on those aimed at recognizing transgender people or reckoning with racist aspects of the country’s history.

“We are going on offense,” DeSantis told a crowd in Iowa in March, when talking about his governing style. “I am sick of people getting elected to office and they kind of sit back like potted plants. They let the media determine the debate, or the left determine the debate.”

It’s this brand of conservatism that DeSantis is betting will take him to the White House, though culture-war issues aren’t his only selling points. He is also expected to continue emphasizing Florida’s approach to the pandemic compared to other states, as well as his landslide victory for his 2022 reelection.

That final point, in addition to the many Republican victories up and down the ballot in Florida in November, poses a direct contrast to Trump, who has been widely blamed for Republicans’ lackluster results nationally during the midterms.

“In 2022, (DeSantis) had serious coattails across Florida. … President Trump, he’s had three election cycles where he has hurt Republicans running for office instead of helped them,” said Ken Cuccinelli, founder of the pro-DeSantis super PAC Never Back Down, which has been running TV ads across the country. “Whether it’s the House, the Senate, governors, state legislative races, Ron DeSantis (as the nominee) will result in more members … being Republican.”

Cuccinelli was formerly a high-ranking official in the Department of Homeland Security in the Trump administration. He is among several top people at the pro-DeSantis super PAC who formerly worked for the president but now say the nation needs a change.

Strengths and weaknesses

Arguably DeSantis’ greatest weapon in the fight ahead is money.

The governor has proven to be a prolific fundraiser who’s attracted support from grassroots Republicans and billionaires alike. He’s sitting on more than $80 million in his former Florida political committee, much of that leftover from his reelection. He’s expected to use those funds in his presidential race even though that may involve exploiting a gray area in campaign finance regulations.

Never Back Down has reportedly raised tens of millions more, though it won’t be required to file paperwork showing the details of those donations until July.

On Wednesday, DeSantis fundraisers began convening at the ritzy Four Seasons Hotel Miami for an event that will include political briefings before attendees make calls to raise money for his campaign. Details were initially hard to come by, even for invitees, as information trickled out, creating a lure of exclusivity. DeSantis’ team is not allowing reporters into the event.

Many expect DeSantis’ greatest liability will be that he is still relatively untested in the national spotlight.

Despite governing the nation’s third-largest state with a robust Tallahassee press corps, DeSantis has rarely granted interviews to mainstream news outlets, preferring instead the friendly questions of Fox News or even somewhat obscure conservative websites.

And as Trump’s growing list of endorsements from Florida’s members of Congress shows, DeSantis has not invested in building deep relationships with other politicians.

In intimate settings with donors or supporters, he is known for sometimes coming across as awkward or aloof and often lacks the warm touch that his wife, Casey, can bring. When one U.S. representative, Greg Steube, a Republican from Sarasota, was asked why he endorsed Trump, he told Politico that DeSantis had never once reached out during Steube’s five years in Congress.

The endorsements were part of a series of pre-announcement setbacks for DeSantis, who also received bipartisan criticism for initially calling the Russian invasion of Ukraine a “territorial dispute.” Disney, which has been in a drawn-out feud with the governor that is tiring some DeSantis supporters, also announced earlier this month that it was scrapping plans to build a roughly $1 billion new office complex in central Florida due to “new leadership and changing business conditions.” Trump has also been attacking DeSantis unrelentingly.

Cuccinelli said it’s not guaranteed that, even as an announced candidate, DeSantis will choose to directly engage with Trump’s attacks.

“I think (DeSantis’) rather indirect approach has been driving the Trump campaign crazy,” he said. “They’d like to see a full-blown hockey fight, and he has shown no inclination to give them what they want.”

Other observers have noted that DeSantis can’t afford to hit back too hard, for risk of alienating the base that he and Trump share.

The attacks and wobbles have amounted to chatter — which his backers have fiercely disputed — that DeSantis’ momentum may be fizzling before he even begins. A recent headline splashed across a recent Sunday front page of The New York Times told the nation that he was “limping to the starting line.”

The critiques mean that DeSantis’ early moves as an official candidate will be closely watched as he seeks to prove he still has momentum.

“He needs to come out of the gate as a serious contender in the early primary states,” said Lauren Zelt, a Republican strategist who splits her time between Key Largo and Washington and formerly worked on Mitt Romney’s 2012 presidential bid.

“There is still time, and especially given the current and looming legal woes of former President Trump, I still believe anything is possible,” she added.

Jim Merrill, a longtime New Hampshire Republican strategist, said the early naysaying will be irrelevant in the long term. Rather, he said people’s early expectations from DeSantis were “completely out of proportion” and now have recalibrated to become more realistic. (New Hampshire’s February primary for Republicans is second in the nation, after Iowa.)

“Donald Trump comes into this primary as the front-runner; he is as close to an incumbent as you can get,” Merrill said. “Gov. DeSantis gets into the race with a lot of positive attributes that suggest he can run an effective and potentially winning campaign, but like in any case, you have to earn it.”

“He starts in an enviable position,” he added. “But now the hard work begins.”