Trump’s Team Is Waging a Gross Campaign to Keep Humiliating DeSantis

Trump on desantis

In the time since Ron DeSantis launched his presidential campaign, Donald Trump has only increased his wide national and state primary polling leads over the Florida governor. With DeSantis 2024 flailing for months, it would perhaps seem natural for the former president to now ease up a bit on thrashing and gratuitously humiliating the Florida governor.

Trump and his senior staff have absolutely no intention of doing that.

Within the upper ranks of Trumpworld, there is an entire sub-industry dedicated to making DeSantis’ life hell, sometimes in a flamboyantly childish, taunting approach that more closely resembles teenage cyber-bullying than it does a White House run. Top Trump aides have near-daily discussions about new and outrageous ideas for how to attack and debase DeSantis, including via the campaign’s regular anti-DeSantis “Kiss of Death” email blasts to supporters and the media, two people familiar with the situation say.

According to a person with direct knowledge of the matter, a recurring inside joke bounced around by Trump 2024 senior staffers is: “We aren’t gonna be done with him until he’s fat again,” a crude reference to the Florida governor’s weight loss. 

The attacks have indeed been juvenile, and at times evidence-free. Earlier this year, Team Trump made a point of publicly going after his former ally’s penis size, while the former president himself has suggested DeSantis might be gay, and posted on social media that his rival may be a pedophile or groomer.

Now, the campaign is shifting focus, with its approach growing even more demented — and way, way grosser — as Trump inches closer and closer to the 2024 nomination.

As of last week, the 2024 GOP presidential frontrunner and his team have gone on the record to assail DeSantis for alleged bathroom-related occurrences. In an email, titled “KISS OF DEATH: #BOOTGATE,” which was blasted out by the Trump campaign on Halloween, Trump’s top spokesman Steven Cheung wrote that “soon” DeSantis is “going to wish for more … in-flight biohazard stories instead of having to deal with his shoes that are more appropriate for America’s Next Top Model than the campaign trail.” 

One point of the email was to mock the governor for his footwear, a troll-tactic that has been successful enough to force an actual response from DeSantis himself. But the reference to DeSantis and an “in-flight biohazard” is perhaps the first public statement that Trump 2024 has made regarding an unverified rumor that has circulated in Trumpland for months now. According to two sources with direct knowledge of the matter, the alleged incident gained such momentum in MAGAworld that prominent Trump allies have tried for months to convince different tabloids and mainstream news outlets to investigate it.

The former president, who has routinely solicited unverified dirt on DeSantis from advisers and politicians, is aware of this rumor, and has gossiped that it shows DeSantis isn’t just “weird” but “disgusting,” one of the sources recalls. Earlier this year, Trump quipped that you can’t have a man like that in the White House, citing the alleged mess.

Somehow, this isn’t even the sole DeSantis hearsay of this kind that Trump has been briefed on over the course of the primary. Earlier this year, according to two sources familiar with the matter, a former House member shared a story with Trump involving a Capitol Hill gym’s locker room and then-Congressman DeSantis.

In the months since hearing the story, Trump has spread the piece of gossip to a number of associates during his private ventings about the governor, one of the sources says, citing direct knowledge. “Did you hear about [Ron] and the locker room?” Trump has at times injected into conversation.

Rolling Stone has not independently verified either story. But Trump’s repeated discussion — including during some primary strategy sessions — of these rumors, along with his campaign’s willingness to fan them, underscores just how much he and his lieutenants have made it their mission not just to defeat DeSantis but to relentlessly demean and emasculate him as much as possible.

In the past month alone, the Trump campaign, or Trump himself, have also gone after DeSantis for his fashion sense (“Ron’s heels are high, his hopes have never been lower”); his manhood (“[Ron] is now a political eunuch. He’s the last person who should be talking about balls”); his brain (“completely fried and inoperable”); his allegedly bizarre eating habits (“stuffing your suit pockets with cold, stale chicken tenders”); and much else. 

This ongoing messaging salvo, says a senior Trump aide, obviously has nothing to do with his policies; it’s to “drive home the point to every voter and news consumer how weird and awkward this guy is … [ideally] so that they don’t even want to be around him or in the same room,” the aide stresses. 

The DeSantis campaign didn’t respond to a request for comment on this story. However, hours after Rolling Stone approached the Trump team for comment on Tuesday, the campaign released another DeSantis-trashing “Kiss of Death” email, which was littered with obvious innuendo.

“Ron DeSanctimonious is failing to gain any traction as he has soiled his campaign by going full Never Trump,” Cheung wrote. “Instead of dropping out with dignity, he has now forever smeared his legacy. No amount of contrition or repentance can wipe away his poll numbers from skidding out of control … For DeSanctus, he will never be anything more than Number 2.” 

Since the summer, Trump’s own determination to ritually embarrass the governor has caused him to float to some confidants that he might bar DeSantis from even speaking at the 2024 Republican National Convention, should Trump win the nomination, according to two sources who’ve heard him say this. Both sources say that if DeSantis were to beg Trump, the former president could easily change his mind.

In recent weeks, another source close to Trump tells Rolling Stone that the former president has said that if DeSantis really wants to stop the MAGA onslaught against him, the governor has to, for starters, drop out of the primary soon, approach Trump very nicely and contritely, and — in Trump’s words — be prepared to “kiss my ass, a lot.”

Team Trump’s salt-the-wound strategy is partly owed to Trump being furious with DeSantis for trying to snatch his crown atop the GOP. It is also due to several of Trump’s top aides and allies having extremely negative experiences with the governor in the past — some while working directly for him — and today striving to completely “destroy” him and crush his political future.

For instance, MAGA Inc., a pro-Trump super PAC, recently resumed its expensive negative ad campaign against DeSantis in the crucial primary state of Iowa. Asked about the ad strategy given Trump’s wide polling lead in the Hawkeye State, a source with direct knowledge of the effort says: “We aren’t satisfied with just beating Ron DeSantis, we are going to end his political career.”

The Trump campaign’s effort to, in the phrasing of some senior aides and operatives, “mindfuck” DeSantis with constant embarrassments has also included a carefully planned, slow-moving rollout of U.S. congressional endorsements for Trump from the Florida delegation earlier this year. It’s been working — and Trump has grown his lead over DeSantis so much in the last several months that GOP megadonors, and major political and media backers, have been losing faith that DeSantis ever had it in him to topple Trump as the party’s kingpin.


“There’s a long way to go, but…[DeSantis] hasn’t risen to the level he needs to rise. At this point in time, I don’t see how he’s going to turn it around … I think it’s gonna be Trump’s game, and at this point in time, I would be shocked if Trump were not the nominee,” veteran GOP strategist Ed Rollins told Rolling Stone back in July, adding that DeSantis isn’t “warm and fuzzy” to voters and that he was “diminishing by the day.”

Rollins, who used to front a pro-Trump group, defected from Trump in the post-presidency to lead the Ready for Ron PAC — to try to help get the Florida governor elected to the White House. The strategist has since abandoned all hope in the would-be Trump heir’s chances.

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