‘Destroy This Guy’: Why Trump’s Campaign Against DeSantis Is So Personal
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Donald Trump loathes Ron DeSantis for the Florida governor’s “disloyal” challenge to Trump’s iron grip on the Republican Party. The former president’s ire, however, is dwarfed by the intense desire harbored by some of Trump’s key aides and allies to see DeSantis politically ruined.
These advisers, lawmakers, and operatives personally know DeSantis or used to work for him. Now, some of them are working to reelect Trump and have brought their intimate knowledge of DeSantis’ operations, and also what makes Trump’s likely 2024 primary rival tick. Just as importantly, some of the Team-DeSantis-turned-Team-Trump contingent have talked to the ex-president about how best to relentlessly mess with DeSantis, assuring Trump that the Florida governor is uniquely “insecure” and “sensitive,” and that it’s easy to get in his head, two such sources who’ve spoken to Trump tell Rolling Stone.
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It’s one of the reasons why the open political warfare between Trump and DeSantis is only expected to get nastier in the coming months. “If Ron thinks the last couple months have been bumpy, he’s in for a painful ride,” says a third source, who used to be on Team DeSantis and is now in the Trump orbit.
This person continues, “The nature of the conversations among the people who used to work for Ron is just so frequently: ‘OK, how can we destroy this guy?’ It is not at all at a level that is normal for people who hold the usual grudges against horrible bosses. It’s a pure hatred that is much, much purer than that … People who were traveling with Ron everyday, who worked with him very closely over the years, to this day joke about how it was always an open question whether or not Ron knew their names … And that’s just the start of it.”
One Trump adviser who also knows DeSantis tells Rolling Stone, “Oh, I’ve told the [former] president several times how easy it is to mindfuck Ron,” adding they’ve told Trump that “[DeSantis] takes little slights and digs incredibly personally and doesn’t really let things go. [Trump] is aware that the Florida governor is tailor-made for him to effectively mess with, until Ron backs down.” Ironically, the title of the prominent pro-DeSantis super PAC is Never Back Down.
Though Trump seems eager to take advantage of DeSantis’ allegedly razor-thin skin, the ex-president and 2024 GOP frontrunner is similarly famous for his own hypersensitivity and penchant for obsessing over jabs from others. He spent time as president trying to convince his own female senior staffer that his penis wasn’t bizarrely shaped, as was alleged at the time. During his 2016 presidential campaign, he couldn’t help himself from feuding with a Gold Star family, simply because they criticized him. He kept feuding with John McCain even after the senator died. While he was leader of the free world, Trump secretly pressed lawyers and political aides on whether his government and Justice Department could investigate Saturday Night Live and other late-night comedy shows for being too mean to him. He directed his own White House staff to lean on Disney to censor late-night host Jimmy Kimmel, an anti-Trump comedian. And the ex-president was, of course, so keen on not letting go of the anti-democratic fiction that the 2020 election had been stolen from him that it caused a deadly riot.
Furthermore, Trump, similar to DeSantis, has his own lengthy running list of former loyalists and officials who’ve since become some of his most bitter enemies.
But no matter for Team Trump, which sees DeSantis’ own insecurities as a massive opportunity.
“Ron is not someone who can just ‘walk it off.’ I know because I made a lighthearted joke to him once, and he got mad and held it against me,” the Trump adviser adds. “Team Trump does not want to just beat him. Team Trump wants to humiliate him maybe more than they’ve ever wanted to humiliate anybody on a national stage … [and] that is what is driving a lot of this.”
DeSantis’ spokesperson did not respond to Rolling Stone’s request for comment on this story.
In recent months, Trump has spoken to an array of advisers, friends, and Republican lawmakers who’ve known or worked closely with DeSantis, and has at times solicited gossip and salacious, unverified details of the governor’s personal life. On top of that, the former president has brainstormed with several of these confidants various ideas for aggressive mudslinging messaging. According to two other sources with direct knowledge of the matter, among the potential targets they see are DeSantis’ physique, attire, appearance, voice, and social skills. They also believe he looks humorously clumsy in his ongoing feud with Disney.
Sometimes, Trump has privately noted that some of these elements would work well if incorporated somehow into eventual 2024 attack ads against DeSantis.
“Donald Trump is an animal. He’s a fighter. In 2016, he went further than what a so-called respectable politician was supposed to do, in how aggressive his attacks against opponents were. It offended some people, but now, he’s pushed the boundary of propriety so far that others are willing to go there in campaigning,” Michael Caputo, a former Trump administration official who remains close to the ex-president, tells Rolling Stone. He adds that some Trump allies are interested in perhaps even harsher attacks than Trump is. “There are people — including at the peripheries of the 2024 campaign — who go after DeSantis even harder, and get even rougher on the governor’s allies,” Caputo says.
Indeed, Trump has already demonstrated that virtually nothing is off limits in his campaign against DeSantis, who hasn’t even officially declared his 2024 candidacy yet. (The governor is clearly running a “shadow campaign” at this time, however.) Last month, the ex-president publicly suggested DeSantis might be gay. The month before that, Trump implied the Florida governor is a pedophile. That the allegations are baseless is not much of a concern to the 2024 Republican frontrunner.
“The only people who like Ron DeSantis are the people who have never met him,” Taylor Budowich, the head of the pro-Trump super PAC MAGA Inc. and Trump’s former spokesman, harshly commented to NBC News last week. Budowich, too, is a DeSantis alum, having worked with the DeSantis transition in Florida.
Stories of DeSantis colleagues and staffers describing the Florida governor as either cold or hostile are legion. Republican political operatives have slammed him as a man who is “missing the sociability gene” and “never says thank you,” even to major donors.
In a blistering 2021 piece, Politico reported on the existence of a so-called “support group” of “scarred” former DeSantis aides who meet to exchange stories on what they described as a nightmare boss that treated anyone not in his innermost circle “like a disposable piece of garbage.”
The irritation with DeSantis is evident in some of the embarrassing stories former staff have floated to the press. Former employees told The Daily Beast of the pudding incident, which reportedly involved the Florida governor shoveling the chocolate dessert into his mouth with three fingers to the disgust and amazement of those accompanying him on a flight to Washington, D.C. The detail went viral and provided the grist for a Trump-aligned super PAC ad riffing on the pudding incident and attacking DeSantis over Social Security policy.
The DeSantis campaign-in-waiting has been rocked by a series of rebukes from donors to members of the state’s Republican congressional delegation.
Over the past two weeks, members of Florida’s Republican congressional delegation have announced their support for Trump one by one and the steady drip-drip of endorsements hasn’t been accidental. As Rolling Stone reported, the slow rollout — planned to inflict maximum humiliation of DeSantis — was helmed in part by Susie Wiles, a former DeSantis aide whom the Florida governor blackballed from his political operation after she helped him win the 2018 governor’s race. According to people with knowledge of the matter, though, Wiles is more restrained, and less colorful, than other Trump acolytes in privately describing her bad experiences with DeSantis.
Rep. Greg Steube, who endured a dangerous fall and lengthy subsequent hospital stay, announced his support for Trump last week. In an interview with Politico, the Florida Republican said DeSantis had repeatedly snubbed or ignored him, including during his hospital stay, in contrast to what he described as a more solicitous and attentive Trump. On Friday, Steube went a step further and blasted DeSantis supporters in the state legislature for “carrying the water for an unannounced presidential campaign” and urged them “not to kowtow to the presidential ambitions of a Governor.”
Other former DeSantis associates have made their intentions toward DeSantisland abundantly clear.
Justin Caporale is a former Trump White House aide who went to work for the DeSantis administration only to return to the MAGA fold as Trump’s top advance man. According to RealClearPolitics, Caporale has already informed DeSantis aides that working on the Florida governor’s recent book tour would blackball them from a future in the Trump presidential campaign or any future Trump White House.
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