When a former top communications staffer for Donald Trump announced in March that he was joining a super PAC supporting Gov. Ron DeSantis’ likely presidential campaign, the news lit up Republican political circles.
To observers of the emerging 2024 primary, the defection of Matt Wolking—who led Trump’s “war room” rapid-response operation in 2020—was one of the clearest signs yet that even MAGA loyalists were ready to jump on the DeSantis train.
“Trump was the president we needed 8 years ago, but to make America great again, our movement needs a disciplined leader who wins instead of loses, never backs down, fights smart, and puts the mission before himself,” Wolking tweeted at the time.
But in the weeks that have followed, Wolking’s move has only continued to curdle the already sour relationships between the camps of the GOP’s two leading presidential contenders—and set the tone for the inevitable squabbles and betrayals that are to come in the 2024 race.
Sources close to Trump’s operation, of course, have tried to downplay the significance of defections from Wolking and a smattering of other former Trump staffers.
One Trump adviser, speaking to The Daily Beast, recalled Trump quipping that his own camp isn’t sending their “best and brightest” or “geniuses” to DeSantis’ orbit. “He used to say that about Mexico,” too, the adviser added.
Reached for comment by The Daily Beast, Wolking didn’t hold back.
“Ron DeSantis is a conservative winner and undefeated fighter who represents the future,” he said. “No one in their right mind who wants to see Biden out of the White House would work for Trump now. In the near future, everyone over there will either be fired, indicted, or working for Laura Loomer anyway.”
A Trump spokesperson did not return The Daily Beast’s request for comment.
In typical Trumpworld fashion, loyalists are promising that former Trump staffers who work for DeSantis will face the ex-president’s considerable appetite for revenge.
Another source that has spoken with Trump in recent months said that he was “laser-focused on destroy[ing]” the Florida governor and ensuring that DeSantis’ staffers would be unable to get a job in his operation moving forward.
While Wolking is a well-liked operative and “really good” when it comes to opposition research, according to one Trump adviser, MAGA operatives have worked overtime to argue that losing him isn’t much of a loss.
Sources told The Daily Beast that Wolking never had much face time with Trump. While Wolking remained so loyal that his Twitter page displayed a Trump tweet wishing him a happy birthday—and still does—one source said it was just a favor passed up the ranks to Trump’s social media guru Dan Scavino, who often tweeted from Trump’s account.
Some operatives still in Trump’s camp argue that Wolking shouldn’t be underestimated. After Trump’s 2020 defeat, the strategist added to his resume with a top role on Virginia Gov. Glenn Youngkin’s successful 2021 campaign.
But others have scoffed at comparisons that DeSantis’ camp drew between him and another prominent Republican who switched camps: Susie Wiles, the former DeSantis strategist turned top Trump 2024 adviser.
“Matt’s a nice guy and a solid operative, but the fact that anyone thinks he’s gonna have a meaningful impact on a presidential race is absurd,” one Republican operative with ties to both DeSantis and Trump aides said.
Wolking isn’t the only Trump staffer to have migrated to DeSantis’ side recently.
Erin Perrine, a deputy communications director from Trump’s 2020 operation, also joined DeSantis’ super PAC. And this past week, the PAC additionally hired Jess Szymanski, a Trump Department of Energy staffer, according to NBC News.
It’s not just the defections that are annoying Trumpworld—it’s how DeSantis’ operation is talking about them.
A different Trump operative close to the 2024 campaign said that the DeSantis PAC is obsessed “with getting press coverage about themselves” by hyping personnel moves and “strategy.”
“Masturbating to reporters. This is all for Jeff Roe’s pleasure and bank account,” they added, name-checking the bigshot GOP strategist now working for DeSantis.
According to these sources, there is a disconnect between how some of DeSantis’ newfound staff and Trump’s staff view their roles—and it plays into the Trumpworld belief that the Florida governor’s team consists of hired guns, not true believers.
“DeSantis operatives are taking lame shots at Trump and then talking to Trump operatives like, ‘This is just the job, we’re still cool,’” said the Republican operative with ties to DeSantis and Trump.
“Meanwhile, Trump operatives are planning to rip out [DeSantis’] liver and eat it with a nice Chianti,” they said, “before making sure anyone who signed on to work for him is permanently relegated to the Never Trump hinterlands of low-dollar political consulting,”
“They’re dealing with savages and acting like it’s a game,” they concluded. “These people are playing for keeps, and the DeSimps aren’t ready for it.”
Despite the tough words from Trump allies, Wolking has also been able to thread a careful needle, with some in the ex-president’s camp still respecting his work.
That said, those in Trump’s ear say DeSantis might have been a bit too welcoming to those who once worked for his top GOP rival.
“You see a lot of these Trump expats going to DeSantis,” said the Trump adviser who heard him invoke his “best and brightest” quip. “It’s a free country, they can do that. But I think DeSantis is a little too eager to take them because they used to work for Trump.”
“Is Trump really losing out by losing them?” the adviser concluded. “Now there are barnacles under DeSantis’ boat at a time when he can not afford to have bad advice.”
Haley grills DeSantis over Disney cheese
The Mickey Mouse primary is kicking into full swing.
After GOP presidential contender Nikki Haley first poked DeSantis over getting outmaneuvered by Disney—even going so far as inviting the company to move jobs to her home state of South Carolina—an outside group supporting her campaign is ratcheting up the effort to tweak the Florida governor over his fight with “the House of Mouse.”
According to a memo obtained by The Daily Beast, the Stand For America PAC plans to call on DeSantis “to put his money where his mouth is and return the more than $100,000 his campaign and affiliated PACs have taken from Disney over the years.”
The pro-Haley group’s messaging leaned heavily into DeSantis’ long-running feud with Disney, which recently moved to the courtroom and potentially complicates the governor’s likely 2024 presidential campaign.
“DeSantis, who currently faces a lawsuit from the House of Mouse over alleged acts of ‘government retaliation,’ has made the corporation the focal point of his anti-woke agenda,” the memo reads. “However, if Governor DeSantis and his team were serious about their fight to bring Disney to its knees, they should be willing to return the nearly $111,000 he accepted from Mickey and his pals from 2013-2021.”
Mark Harris, the PAC’s lead strategist, echoed Haley’s own messaging from the stump, arguing that DeSantis has “made it his mission to target one of Florida’s largest job creators to bolster his profile for a race he claims he’s not a candidate for.”
Even if DeSantis hasn’t entered the race, he still rates far higher than Haley in most GOP primary polls. But the former South Carolina governor and onetime Trump ambassador to the U.N. clearly believes she can cut into DeSantis’ support by highlighting his vendetta against a classic American company whose brands remain widely popular among the broader public.
Asked to respond, a representative for DeSantis’ Never Back Down PAC pointed The Daily Beast to their “Mikki Haley” ad, which interspersed Haley’s encouragement for Disney to move to South Carolina with video of Disney employees expressing pro-LGBTQ views.
General election polling more than 500 days out from the first ballots being cast is about as valuable as shares of Silicon Valley Bank stock.
Still, that isn’t stopping the Trump campaign from leaning heavily on them in their latest messaging blitz: a recent memo from top Trump campaign advisers declared “the complete collapse” of DeSantis’ viability in a potential matchup with President Joe Biden in November 2024.
While several of the recent general election matchup polls have had Biden within the margin of error against both Trump and DeSantis, the trend for the Florida governor doesn’t bode well.
DeSantis went from leading Biden by between 3 and 8 percentage points in the polls compiled by RealClearPolitics at the beginning of April to trailing him by six in the latest Emerson poll and by three in the Economist-YouGov survey.
In Harvard’s Harris poll from mid-April, which also included hypothetical matchups between the two GOP frontrunners and Vice President Kamala Harris, DeSantis continued to lag behind Trump.
There was one silver lining in that poll for Team DeSantis: When voters were asked if they supported the governor in his fight against Disney,” 56 percent of respondents supported him—including 42 percent of Democrats and 54 percent of independents.
Full and Total Endorsement News
In an otherwise slow week for 2024 presidential endorsements, DeSantis snagged a big win in all-important New Hampshire—the backing of State House Majority Leader Jason Osborne, who called the Florida governor “exactly the leader America needs today.” The nod comes after Trump returned to the Granite State last week and rolled out more than 50 endorsements from local lawmakers.