The Quiet Way Trump and DeSantis Are Preparing for a Fight

The universe of GOP staffers is a notoriously small one, where even the most diametrically opposed Republican politicians often have overlapping orbits between their staffs. But there are two GOP stars with remarkably little overlap: Donald Trump and Ron DeSantis.

According to publicly available filings, LinkedIn profiles, and sources with knowledge of hiring decisions in both camps, the vast majority of staffers now within DeSantis’ ranks have zero connection to Trumpworld. While there are a few exceptions, the overwhelming majority of DeSantis staffers are not former Trump people, and the vast majority of Trump’s inner circle was never in DeSantis’ camp. The Daily Beast cross-referenced more than 600 names between the two operations and found an unusually small amount of crossover for such sprawling GOP networks.

There are some notable, if not tenuous, exceptions. Susie Wiles—now a close adviser in Mar-a-Lago—was a “top adviser” to the Florida governor. DeSantis’ chief of staff, James Uthmeier, worked in Trump’s Commerce Department. DeSantis campaign staffers Amanda Robbins Vargo and Kelly Kundinger both served stints in the Trump White House. And a few DeSantis staffers held short-term internships with Trump-related operations.

But the two favorites for the 2024 GOP presidential nomination seem to have quietly avoided hiring staff who have worked for their would-be competitor.

In fact, the exceptions to this hiring détente seem to prove the rule.

In 2019, DeSantis fired Wiles from his operation amid “rising tensions,” according to CNN. A Politico story at the time recounts how Wiles went from Trump’s 2016 campaign to DeSantis’ 2018 governor bid. Trump, who apparently credits Wiles for winning him Florida in 2016, reportedly told DeSantis that hiring Wiles was “the smartest thing you’ve ever done.”

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But when emails were leaked showing DeSantis appearing to sell access on golf trips to lobbyists, Wiled was fired for supposedly leaking the emails. Trump then hired Wiles to his reelection campaign—only for DeSantis to reportedly push for her firing there. Trump’s campaign obliged, but the former president reinstated her shortly after.

The entire episode seems to have endeared Wiles to Trump—and Trump to Wiles. She is now one of his closest advisers and one of the few aides in Trump’s inner circle with insight into DeSantis’ thinking, positioning her as a potential campaign manager for 2024.

And as both GOP leaders eye a potential 2024 run, the two are set to hold competing rallies in Florida this coming weekend.

Trump will hold a rally with Sen. Marco Rubio (R-FL) in Miami on Sunday. On the same day, DeSantis will hold his own campaign event—without Trump—just south of Tampa.

The approximately 240 miles between the two venues could offer some much-needed breathing room for Trump and DeSantis. While each man has largely avoided criticizing the other, it’s been clear to anyone paying attention to GOP politics that something is brewing.

There are a number of ways in which a competition could turn nasty, but perhaps no faster way than Trump going after one of DeSantis’ closest advisers: his wife.

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After fighting off cancer this past March, Casey DeSantis’ role has continually grown, according to an outside adviser. She has turned into a de facto point person for the “very insular” campaign, in the words of a person familiar with the operation.

“She is a campaign manager, the political director, and the chief of staff,” this source said.

A Trump adviser noted that the former president’s camp was also aware of Casey DeSantis’ outsized role—and this adviser identified that role as a potential weakness.

“The main thing everyone makes fun of DeSantis for is that everyone knows his wife is the one calling the shots. He’s totally subservient to her ridiculous political opinions,” this adviser said.

The adviser added that Casey DeSantis was an easy target for Trump.

“Trump’s going to end up doing to DeSantis and his wife what he did to Cruz and his wife,” the Trump adviser said, referring to how Trump attacked Sen. Ted Cruz’s (R-TX) wife during the 2016 Republican presidential primaries.

Responding to these claims, Trump spokesperson Liz Harrington said theories that Trump would attack DeSantis’ wife were “total bullshit.”

While it’s clear there’s potential for an explosive battle between Trump and DeSantis, it’s also possible DeSantis chooses to pass.

Vanity Fair reported this week that DeSantis has been telling GOP donors he won’t challenge Trump in 2024 if the former president runs. Instead, a source told Vanity Fair that DeSantis would wait and then waltz to the nomination in 2028.

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Nothing is certain, however. The piece also noted that the two men “hate each other,” according to a former Trump adviser, and a Republican close to DeSantis said the Florida governor could also kick start a presidential campaign soon after the midterms.

Trump advisers seem to believe that, if DeSantis did challenge Trump, the former president would make quick work of the Florida governor.

“It doesn’t matter what might be best, Trump is going to try to destroy him,” one adviser told The Daily Beast.

Trump’s animus toward DeSantis is apparently so strong that there’s been a concerted effort to stop him seeing one particular NRCC email. The email in question, in which donors are asked to vote who’d be the best nominee in 2024, is thought to be so explosive that a well-placed source in Trumpworld said the former president almost certainly hadn’t seen it—because if Trump had, “that’s one of those things that would generally elicit a reaction.”

Another point of criticism aimed at DeSantis from Trumpworld is how the Florida governor offered up a blank stare when Democratic gubernatorial candidate Charlie Crist asked if he’d commit to serving a full four-year term. If DeSantis had agreed to such, he’d have taken his name out of the hat for 2024.

Instead, DeSantis ignored the question and still hasn't answered it more than a week later.

That DeSantis debate moment alone has left some advisers nervous.

When The Daily Beast asked a source close to Trump for a reaction to the debate moment, the source responded with a blushing emoji. Others in Trump’s universe seized on the DeSantis blank stare and saw it as an opportunity to attack, which Trump reportedly already does in private.

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Longtime Trump friend Roger Stone went after DeSantis over the debate flashpoint and said the current Republican governor had a “deer-in-the-headlights moment.”

Stone has repeatedly noted that DeSantis is weaker than people think. Stone says DeSantis lacks Trump’s charisma, a sense of humor, and stamina. But DeSantis also lacks another thing compared to Trump: ongoing legal battles.

Hanging over Trump’s head is the possibility that he may face some criminal liability for Jan. 6, as well as liability in a number of other cases.

DeSantis has no such legal baggage, and if charges were to materialize and derail Trump’s 2024 plans, DeSantis is almost certainly best-positioned in the GOP to win the nomination.

And even though their staffs are quite distinct, DeSantis has turned many Trump loyalists into DeSantis fans.

Among those millions of GOP voters who hold favorable views of both men, two are prominent Trump supporters: Sarah Huckabee Sanders and David Bossie.

According to multiple sources that spoke with The Daily Beast, Huckabee Sanders (Trump’s former White House press secretary now running for Arkansas governor) and Bossie (a longtime Trump friend) have become friendly with DeSantis. Specifically, Huckabee Sanders has befriended Casey DeSantis, and Bossie has become an informal adviser.

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Still, the potential of a real fight between Trump and DeSantis is looming—perhaps one of the reasons they’re keeping their staffs so separate. And even if Trumpworld is projecting confidence, polling has suggested a tight battle.

In Florida, a recent poll showed GOP voters preferring DeSantis to Trump—47 percent to 40 percent. And a recent New Hampshire poll—the state which holds the first in the nation primary—also showed voters preferring DeSantis over Trump.

But those polls don’t factor in Trump’s brawling style of politics, and his advisers remain confident that DeSantis would fold easily if they actually went head to head.

One Trump adviser compared the former president to Muhammad Ali.

“DeSantis isn’t a worry,” this adviser said. ”It’s more like something to grab a bag of popcorn and watch. DeSantis is used to making local reporters look dumb, but now he’s stepping into the ring with Ali.”

—with additional reporting by Jake Lahut

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