Trump Spent Weekend Stewing That ‘Wiseguy’ DeSantis Won’t Kiss His Ring

·5 min read
Photo Illustration by Kelly Caminero/The Daily Beast/Getty
Photo Illustration by Kelly Caminero/The Daily Beast/Getty

Former President Donald Trump spent the long MLK Day weekend in reflection but not on anything related to the civil rights icon. Instead, he was fixated on one burning question, according to two people familiar with the matter:

Is he being a wiseguy?”

The “wiseguy” was none other than Florida governor Ron DeSantis, a fellow Sunshine State resident and Republican Party star who just last week had gently dinged part of Trump’s record as president.

In recent weeks, if you’ve run in the ex-president’s inner circle or floated in and out of his social or political orbits, chances are high that you’ve heard Trump casually insulting DeSantis, even in conversations that initially had absolutely nothing to do with DeSantis.

Ever eager to protect his turf and with an eye on 2024, Trump has gossiped with certain confidants and advisers about DeSantis’ political vulnerabilities and “weaknesses,” according to the two sources familiar with the situation, and another person with direct knowledge of the matter. On a number of occasions, the twice-impeached former president has lately told associates that if they’re asked about the DeSantis-Trump tensions on TV, they should decline to confirm or deny the existence of a simmering cold war between the two conservative icons.

Instead, the former president has instructed, the Trump allies should stress that the ex-president is the “undisputed” leader of the Republican Party, and that if Trump runs to reclaim power in 2024, there is nobody else in the party who could come close to beating him. Indeed, when behind closed doors, the former president is fond of saying he would easily “destroy” DeSantis in a hypothetical intra-party race.

The source with direct knowledge recounted that in one private conversation earlier this month, Trump sounded “confused” about why DeSantis wasn’t simply coming out and saying that the 2024 GOP nomination is Trump’s, if he wants it. This source added that the former president, who remains staggeringly popular among Republican voters, rhetorically asked if DeSantis “remember[ed] what happened” in the 2016 primary, during which Trump humiliated and steamrolled over his prominent conservative rivals like Ted Cruz and Marco Rubio.

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Just last week, in a veiled jab at DeSantis and other “gutless” Republicans who get vaccinated and boosted but refuse, as Florida’s governor has done, to disclose that status, Trump told OAN that “You gotta say it, whether you had it or not, say it.”

Spokespeople for Trump and Gov. DeSantis did not respond to requests for comment from The Daily Beast.

The ballooning animosity toward DeSantis, which Trump’s lieutenants have tried to keep from spilling into public view, is yet another example of how the former president has been working to maintain his iron grip on the Republican Party, and seeking to weed out non-Trump-sycophants from the party’s upper ranks.

The New York Times reported on Sunday that Trump now refers to a statement from DeSantis forswearing a presidential run if Trump is in the race as “the magic words”—a statement the Florida governor has so far refused to make. Similarly, Axios ran a story this weekend on how Trump is “trashing Ron DeSantis in private as an ingrate with a ‘dull personality’ and no realistic chance of beating him.”

Numerous Trump pals and informal advisers have already stated that the ex-president has privately assured them that he plans to run against his successor Joe Biden in the next presidential election. When publicly pressed on the topic over the past year, Trump has consistently remained cagey.

Recent polling from the University of Massachusetts paints DeSantis as the second most popular potential 2024 candidate among Republicans but one who trails the frontrunner, former President Trump, by a hefty 35 points.

However, whether he ends up declaring or not, Trump has regularly taken the temperature of donors, conservative politicians, and other influential Republican figures, to determine who is definitely with him ahead of 2024, and who may be going wobbly. For now, he is increasingly viewing DeSantis as a primary nuisance, possibly standing in the way of what he hopes to be a leisurely MAGA coronation.

DeSantis, who typically polls the strongest in 2024 GOP surveys, when the 45th U.S. president’s name is excluded—had made what Trump dubbed the “wiseguy” remarks last week to the “Ruthless” podcast, in which the Florida guv took an implicit swipe at Trump’s presidential record on the initial COVID-19 response.

DeSantis remarked to the podcast’s hosts that one of his top regrets while leading Florida was not pushing back “much louder” at the dawn of the coronavirus pandemic against lockdown measures—measures that then-President Trump and other senior administration officials were at the time promoting.

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In Trumpland, the remark did not slip by unnoticed, with several allies flagging it for the ex-president’s attention. And while these burgeoning tensions between the two Republican leaders are, ostensibly, based partly on disagreement over COVID era policy and vaccine messaging, the pair were closely aligned during the Trump presidency, including for much of the coronavirus crisis.

Both DeSantis and Trump have spent much of the pandemic downplaying the severity of the COVID-19 pandemic and ridiculing public-health measures to mitigate it, contributing to Republican men’s status as the most vaccine-hesitant demographic in polls.

Trump, whose administration rushed forward the development of COVID-19 vaccines under “Operation Warp Speed,” repeatedly rebuffed suggestions by supporters and former administration officials to come out as a forceful advocate of the jabs. And DeSantis has taken every opportunity to gut vaccine mandates and promoted monoclonal antibodies as an alternative to vaccination.

But while DeSantis has remained tepid on vaccines and masks, Trump has more recently shifted his tone on vaccines and more pointedly endorsed shots over the past two months—following his lengthy period of refusing to commit to even just a PSA campaign and aggressively fundraising off of vaccine “FREEDOM” propaganda.

In interviews over these recent weeks, the former president revealed that he received a COVID-19 vaccine booster shot, said he’s “very proud of the vaccines,” and “that the results of the vaccine are very good”—all to a vocal backlash from diehard MAGA fans.

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