Trump’s efforts to overshadow DeSantis in Florida take center stage

Nov 4, 2023, 7:17 PM

Former President Donald Trump and Florida Gov. Ron DeSantis are pictured in a split image.
(Getty I...

Former President Donald Trump and Florida Gov. Ron DeSantis are pictured in a split image. (Getty Images)

(Getty Images)

(CNN) — A Florida Republican lawmaker, after flipping his support to former President Donald Trump, is now publicly questioning Gov. Ron DeSantis’ support for the Jewish community. Another state lawmaker, spurned by DeSantis earlier this year, is actively recruiting more of his colleagues to jump on the Trump bandwagon. Meanwhile, a cadre of former DeSantis political operatives who stopped working for the governor on poor terms are now entrenched in Trump world and motivated to embarrass their former boss.

Welcome to the 2024 Revenge Tour.

In the tug of war for home-state supremacy, Trump has gained the upper hand in part by exploiting rifts between DeSantis and Florida Republicans. The strategy has played out easier than the former president’s team anticipated, as DeSantis has left a wake of ill will in the state on the path to political stardom.

As the 2024 campaign descends on Florida in the coming days, the ever-evolving relationship between the state’s Republicans and these two leading figures will be on full display.

Trump, DeSantis and the rest of the GOP primary field addressed Florida Republicans at a state party event Saturday just outside Orlando. DeSantis had a midday time slot, sandwiched between Florida Sen. Rick Scott, his predecessor in Tallahassee who he doesn’t get along with, and state Rep. Randy Fine, the state’s only Jewish Republican lawmaker who recently asserted DeSantis hasn’t done enough to stop Nazis and antisemitism in Florida. Scott announced Thursday he was endorsing Trump, while Fine switched his allegiance to the former president last month.

DeSantis not concerned

In his remarks Saturday, DeSantis said he was not concerned about Florida state lawmakers flipping their endorsement to Trump, telling the audience, “It’s a dynamic thing.”

“No, look — this happens in these things. I mean, we’ve had flips the other way in other states,” DeSantis said, adding that “politicians do what they’re gonna do.”

Trump closed out the gathering, touting the new endorsements from Florida lawmakers and bringing several of them onstage. The crowd laughed and cheered as Trump bashed DeSantis over his slip in national and state polls.

The Sunshine State battle will continue Wednesday, when the Republican Party will hold its third presidential debate in Miami. Trump, who is skipping the debate once again, has scheduled counterprogramming just down the road in Hialeah. The next day, Trump will host Florida Republicans at Mar-a-Lago, a continuation of his courtship of party leaders and donors, while DeSantis will attend fundraisers in the state.

At the same time, in a demonstration of DeSantis’ continued command over the GOP-controlled state Legislature, lawmakers are returning to Tallahassee next week at his urging to pass new sanctions against Iran following Hamas’ attack on Israel last month. They will also seek to address the state’s property insurance crisis, a concern that continues to generate negative headlines for DeSantis back home.

The governor’s influence in the Sunshine State, once unquestioned, has repeatedly taken hits in recent months. His struggles as a presidential candidate have emboldened some Republicans here to break from DeSantis less than a year after he orchestrated the most dominant electoral victory in a Florida gubernatorial race in modern history. With the Iowa caucuses fast approaching, Trump’s lead in early nominating states and national polls appears sturdy while DeSantis has slipped into a distant second place alongside a surging Nikki Haley, the former South Carolina governor.

His attempts to reassert himself as the state’s dominant political force have repeatedly run into enemies he has accumulated over the past decade.

While DeSantis dismissed Fine as seeking “15 minutes of fame,” the governor’s allies are bracing for more state lawmakers to change their allegiance. One DeSantis adviser said they expect as many as six Republicans in the Legislature to flip sides, mostly freshmen lawmakers elected last year.

State Sen. Joe Gruters, a former state party chair who DeSantis regularly iced out, is helping to lure more Republicans to Trump and said he expects to have a “pretty good group” to announce in the coming weeks. He conceded, though, that most lawmakers will remain behind DeSantis, which he attributed to the persuasive power of the governor’s line-item veto authority — a reality he experienced firsthand when DeSantis cut his projects out of the state budget earlier this year after Gruters endorsed Trump.

Gruters recently secured another key win for Trump in the Sunshine State: overturning an attempt by DeSantis allies to force presidential candidates to sign a loyalty pledge to make Florida’s primary ballot. The overwhelming vote to scrap the proposal demonstrated Trump’s enduring popularity among Republican Party officials and served as a crushing defeat for DeSantis loyalists.

“That was like throwing the hammer down,” Gruters said. “That reconfirmed that this is the president’s party.”

State House Speaker Paul Renner said most Republican lawmakers are behind DeSantis because he has demonstrated he’s better positioned to carry GOP successes in Florida to the national stage.

“Elections are about the future and not the past,” Renner said. “Those of us that live here and those of us that work closely with his team know this is a guy that delivers results.”

DeSantis’ campaign insists the governor remains well positioned in his home state. Spokesman Andrew Romeo noted that DeSantis maintains the support of most elected officials “despite running against a de facto incumbent president.”

“The governor will win his home state because Floridians want to see a fighter who will bring the same type of results-oriented leadership to Washington that he has provided in the Sunshine State,” Romeo said.

Former DeSantis staffers

Still, many of the Trump advisers and aides working hardest to keep DeSantis from the White House are people who used to call him their boss. Trump’s team is quick to point out that most of these individuals first worked for Trump and their return to him isn’t surprising. However, some harbor deep-seated and personal animosity toward DeSantis after acrimonious divorces — at times exceeding Trump’s own annoyance at his onetime ally for his supposedly “disloyal” decision to mount a competing presidential bid.

The volume of ex-DeSantis staffers within Trump’s political operation has led some advisers to joke that the former president’s campaign should be called “the 2024 revenge tour.”

Among them is Trump’s top campaign adviser, Susie Wiles, one of the state’s most successful political operatives in recent memory. She took over DeSantis’ campaign for governor in 2018 after early struggles and led him to a narrow victory, but she was pushed out of his inner circle the next year after a public falling out. DeSantis then successfully lobbied for her to be fired from Trump’s reelection team, CNN previously reported, though she was eventually welcomed back and now sits atop his third White House bid.

DeSantis also purged staffers seen as more loyal to Wiles. Justin Caporale, an experienced aide, and James Blair, a seasoned political consultant who became DeSantis’ deputy chief of staff, were pushed out of the governor’s office — both now work for Trump’s campaign. Jennifer Locetta, a former state party executive director who two sources say DeSantis ousted, recently joined the staff of a super PAC that supports Trump.

Meanwhile, Trump’s Florida political operation is spearheaded by Brian Hughes, a longtime GOP strategist in the state who served as one of the architects of DeSantis’ successful first congressional run in 2012. After winning DeSantis declared he didn’t need a political adviser anymore to maintain his safe Republican seat, according to a person who previously worked for DeSantis.

“He’s burned a lot of bridges,” the person said. “And then he puts fire on it so you can never rebuild it.”

Many of these advisers and aides have intimate knowledge of what makes the governor tick, giving them a leg up in a race that until recently had been dominated by Trump and DeSantis.

DeSantis’ frayed relationship with Florida’s consultant class has left him with fewer experienced campaign operatives than Trump in a state that is not only symbolically significant to both but is also a weighty mid-March delegate prize in the nominating fight. He recently split with another top adviser, campaign manager Generra Peck, who commanded his historic reelection last year. Marc Reichelderfer, a longtime Republican operative in the Sunshine State, is now overseeing preparations in Florida.

Trump, though, is also known to burn through staff and advisers, and not all have remained loyal to him. A super PAC supporting DeSantis, Never Back Down, was founded by Ken Cuccinelli, a former official in Trump’s Department of Homeland Security. The organization’s communications team is led by Matt Wolking and Erin Perrine, two veterans of Trump’s reelection campaign.

Florida Senate President Kathleen Passidomo, a close DeSantis ally, said she has found the governor to be collaborative and attentive.

“I have had nothing but good dealings with the governor,” she said. “The things that I read in the press that people are saying about him, I never saw. A lot of the things I read are coming from people who want to get somewhere else in politics and not what’s in the best interest of our state.”

In a statement to CNN, Trump campaign spokesman Stephen Cheung said “any talk about personal grievances towards any primary candidate is misguided.”

“Everybody on the campaign is focused on helping President Trump win the primary election – which he is dominating the competition by wide margins in every single poll – and defeating Crooked Joe Biden in the general,” Cheung said.

Upstaging the governor

The personal vendettas help explain the lengths that Trump and his allies have traveled to upstage the Florida governor.

Last spring, while DeSantis sought to build support on Capitol Hill, Trump planned a dinner at his Mar-a-Lago resort with members of the Florida congressional delegation in a bid to court support on their shared home turf and embarrass the governor.

In the 24 hours ahead of DeSantis’s visit to Washington, some of those representatives began announcing their support for Trump one by one, in a seemingly coordinated effort.

Still, no one in Trump’s inner circle expected Rep. Greg Steube to share such detailed disdain about the governor when he announced his support for the former president, telling Politico that DeSantis has never reached out to him, even after an accident landed him in intensive care. Nor did they initially foresee Donalds, thought to be a close ally of the governor, backing Trump before DeSantis even entered the GOP presidential primary.

Later, rubbing salt in the wound, the former president traveled to the Iowa State Fair with many of those House members – an entourage largely designed to troll DeSantis, who was making a simultaneous appearance.

When DeSantis launched a national tour to promote a new book last spring, Caporale, a longtime Trump aide, privately discouraged Republican operatives from working for the Florida governor or face excommunication from Trump world. Caporale made it clear at the time that this extended to a potential Trump White House. A source said this is no longer in effect as DeSantis has slipped in the polls.

Gruters said people will ultimately gravitate toward who they think has the best chance of winning and added that he harbored no ill will toward DeSantis.

“I think Ron DeSantis has been a good governor of Florida,” he told CNN. “And I look forward to having him come back as governor.”

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Trump’s efforts to overshadow DeSantis in Florida take center stage