GOP insiders think DeSantis could beat Trump in 2024. Here's how.

·14-min read

Rarely has a rising politician thrilled party regulars the way Ron DeSantis is thrilling Republicans right now.

"If you were scripting a perfect Republican presidential candidate, the list of preferred requirements would read something like DeSantis' resume," broadcaster Piers Morgan swooned in the New York Post last month.

Like other conservative commentators, Morgan touted DeSantis’s relative youth (he’s 43); his honors degrees from Yale (undergraduate) and Harvard (law); his time as a Navy lawyer, which took him to Guantánamo and Iraq and won him a Bronze Star; and most of all his reign as governor of Florida, where he has muscled his way into the middle of every contemporary culture war from COVID-19 to "critical race theory" — and banked over $100 million for his PAC and his 2024 reelection bid, a staggering sum for a state-level race.

"I think [DeSantis would] destroy beleaguered Joe Biden — or any other Democrat, for that matter — to win the presidency," Morgan predicted.

Florida Gov. Ron DeSantis and former President Donald Trump.
Florida Gov. Ron DeSantis and former President Donald Trump. (Photo illustration: Yahoo News; photos: Marco Bello/Reuters, Harrison McClary/Reuters)

There's only one roadblock. He has to destroy Donald Trump first.

The reason MAGA pundits are even mentioning Ron and Don in the same sentence is simple. Amid growing legal troubles and a deluge of damaging revelations by the House select committee investigating his supporters' insurrection on Jan. 6, 2021, Trump’s viselike grip on the Republican electorate may be slipping. According to a recent Yahoo News/YouGov poll, more than 4 in 10 Republicans say either that Trump shouldn't run for president again (27%) or that they’re not sure (17%). Among all voters, a majority (52%) now think "Trump committed a crime by trying to overturn the results of the 2020 presidential election," and even more (54%) think the U.S. Department of Justice should prosecute him — numbers that could make some Republicans wary about his ability to win a general election.

Meanwhile, DeSantis seems to be growing stronger. When asked to choose between the two potential 2024 candidates, fewer than half of registered voters who identify as Republicans or Republican-leaning independents say they would pick the former president (45%), according to the Yahoo News/YouGov poll. Nearly as many say they would prefer DeSantis (36%). GOP primary polls in key states such as New Hampshire, Michigan and Florida already put DeSantis in the lead (or close to it), and he has swept straw polls of GOP insiders in Wisconsin and Colorado in recent weeks. In September, he will headline the Republican National Committee’s fall retreat.

A supporter of Florida GOP gubernatorial nominee Ron DeSantis waves a sign at a 2018 campaign rally.
A supporter of Florida GOP gubernatorial nominee Ron DeSantis at a 2018 campaign rally in South Daytona Beach, Fla. (Paul Hennessy/NurPhoto via Getty Images)

It's a remarkable showing for a state-level politician who just four years ago was an obscure congressman in an uphill battle to become Florida’s governor. On Capitol Hill, DeSantis was mostly known as a founding member of the far-right Freedom Caucus and a frequent Fox News guest; he barely defeated his Democratic opponent in 2018. But since then he has become a "conservative folk hero" by loudly railing against what he considers the excesses of the left — closing schools and restricting businesses because of COVID-19; teaching students about structural racism and gender identity; wearing masks — and then trolling liberals with laws that steer his state the opposite way. As a result, DeSantis has been called "Trump with a brain"; his brand of politics, "competent Trumpism." And he keeps rising in the polls.

"I think DeSantis is the favorite right now," Jon Schweppe, policy director of the American Principles Project, a populist conservative think tank, told Yahoo News. "Whether or not — but even if — Trump runs, I think DeSantis can win."

The question, though, is how. Is there a message that can actually pry Republican voters away from Trump after years of blind devotion? And can DeSantis credibly deliver it? Or is he doomed to follow in the footsteps of nearly every other Republican who has defied the former president?

DeSantis is hardly the first to consider toppling Trump.

Before the "Apprentice" star’s dominance was fully established in 2016, more than a dozen GOP hopefuls tried to stop him from securing their party’s nomination. Nothing they did — from ignoring him (Jeb Bush) to excoriating him (John Kasich) to buttering him up (Ted Cruz) to mocking the size of his hands (Marco Rubio) — worked. Trump won 45% of the vote in a crowded field and nearly three times as many delegates as anyone else.

Now a comeback bid in 2024 looks to be less a matter of if than when.

"In my own mind, I’ve already made that decision," Trump told New York magazine last week. "My big decision will be whether I go before or after [the 2022 midterm elections]."

Despite Trump’s somewhat depleted state, he would still enter any 2024 GOP primary contest as the prohibitive favorite. So far every national poll that pits him against the rest of the potential field — as opposed to just one challenger at a time — shows the former president with a large plurality of the vote; many put him over 50%. Trump’s small-donor base is huge; his psychological hold on the average Republican primary voter is unshakable; his sway over party officials is undimmed; and even without access to Twitter, his ability to command media attention remains unrivaled.

For many younger Republicans who plainly want to be president someday — ambitious strivers such as Sens. Tom Cotton of Arkansas or Josh Hawley of Missouri — a third Trump effort would likely prevent them from launching a first attempt of their own. Ex-Trump officials who have been flirting with a White House run — former United Nations Ambassador Nikki Haley, former Secretary of State Mike Pompeo — would struggle to circumvent their old boss. Former Vice President Mike Pence, at least, seems determined to make a go of it. But actual Republican voters are less enthusiastic about that prospect, with just 18% saying they would back Pence over Trump in the latest Yahoo News/YouGov survey.

Former Vice President Mike Pence speaks to supporters.
Former Vice President Mike Pence speaks to a crowd of supporters in Chicago in June. (Jim Vondruska/Getty Images)

As Trump put it to New York magazine, "I think a lot of people would not even run if I did … because, if you look at the polls, they don’t even register. Most of these people. And I think that you would actually have a backlash against them if they ran."

Yet DeSantis appears undaunted. He has pointedly refused to seek Trump’s endorsement for his Florida reelection bid — or to rule out a run against Trump in 2024. He has criticized COVID policies under the former president. And he has raised more money than Trump so far this year — including huge sums from six- and seven-figure Trump donors. (Trump himself has raised $140 million.)

"DeSantis doesn't strike me as someone who would be afraid to challenge Trump," said Republican strategist Mike DuHaime. "I don’t know if DeSantis will run, but I don’t think he’s afraid to."

"I think DeSantis believes this is his best time to run and Trump is at his weakest," said veteran pollster Michael Cohen, managing director at Purple Strategies. "No one else is even close — and that is without DeSantis engaging him yet."

If Trump and DeSantis do decide to go toe-to-toe, they could dominate fundraising and media coverage, making it harder for other candidates to break through.

And a smaller field could put the Florida governor in a better position to consolidate the non-Trump vote than his counterparts in 2016.

"The only way [Trump] gets beaten for the nomination is if maybe somebody is able to run a one-on-one campaign against him — probably DeSantis," lawyer George Conway, one of Trump’s most outspoken conservative critics, recently predicted.

Attorney George Conway.
Attorney George Conway, a conservative critic of Donald Trump, in 2019. (Georgetown Law School handout via Reuters)

So far, Trump and DeSantis have refrained from crossing each other in public. For his part, Trump seems to believe that taking credit for DeSantis’s career — he backed the Floridian’s 2018 gubernatorial bid early — might somehow dissuade the governor from challenging his supremacy. "Well, I get along with him," Trump said last month when asked if he’d be willing to offer DeSantis the VP spot in 2024. "I was very responsible for his success, because I endorsed him and he went up like a rocket ship."

Behind closed doors, however, Trump has "privately questioned DeSantis' loyalty while also raising questions about whether DeSantis is personable enough to win over voters," according to Politico. (Neither the Trump camp nor the DeSantis camp responded to requests for comment.)

Meanwhile, those around DeSantis reportedly see the Jan. 6 hearings as a "shit show" that is "exhausting" the GOP donor class — and might even end up sidelining Trump before 2024.

"That’s where [DeSantis’s] head is at," a Republican consultant familiar with the governor's thinking recently told Politico. "He thinks the goal here is to get Main Justice to go after him. That’s what Ron thinks this is all about."

Both men, in other words, may be hoping to avoid a head-to-head contest. But neither should bet on the other backing down. Assuming they do face off in 2024, then can DeSantis really dethrone The Donald?

Republican strategists say it's possible — but only if DeSantis can convince enough base voters that Trump has finally become the very thing he has spent his entire life desperately trying not to be: a loser.

Sarah Longwell, an anti-Trump GOP strategist, tweeted this week about a sudden shift that she’s been seeing in her focus groups.

"Just had another focus group of Trump voters where ZERO wanted Trump to run again in 2024," Longwell wrote. "Really a striking departure from dozens and dozens of focus groups pre-Jan. 6 hearings when at least half of any Trump-voting group wanted him to run again. His support is noticeably softer."

Sarah Longwell, an anti-Trump GOP strategist.
Sarah Longwell, an anti-Trump GOP strategist, in 2017. (Rick Bowmer/AP)

The reason, according to Longwell, isn't the hearings per se, which Trump voters still see as a "witch hunt." Rather, it’s the way the hearings remind them of "how much baggage Trump has."

Republicans "want someone who can win in 2024 and [they] are increasingly unsure he can," Longwell concluded.

DeSantis’s goal would be to crystallize that concern — then offer himself up as a winning alternative. He could point to President Biden's approval rating: just 38% right now, lower than any other modern president at this point in his first term (including Trump and Jimmy Carter). He could note that, despite Biden's paltry numbers, the damaged Democrat is still leading his predecessor in most nonpartisan national polls. And without directly contradicting the "stolen election" lie that has sadly become table stakes for GOP candidates in the Age of Trump, he could remind his fellow Republicans that Trump has never actually won the national popular vote.

Trump is still the GOP alpha, Schweppe said, so attacking him directly will almost certainly "backfire." But if Republican voters are "presented with an alternative they think is even stronger — who happens to maybe be more electorally viable in a head-to-head matchup with a Democrat, with Biden or whoever — I think they're going to jump at it."

If DeSantis can destabilize Trump, Republican strategists say, it wouldn't be hard for him to pivot to a positive case for his own candidacy. "It’s a message that's very forward-looking, but also not anti-Trump," Schweppe said. "Let's go defeat woke-ism. Let's run it out of our institutions. Let's take this country back and actually make America great again."

President Biden delivers his inauguration speech on Jan. 20, 2021.
President Biden delivers his inauguration speech on Jan. 20, 2021. (Patrick Semansky/AFP via Getty Images)

DeSantis, he added, is "an excellent messenger for that" because of "everything he's done" in Florida — a MAGA-heavy résumé that includes reopening schools early, railing against COVID mitigations, yelling at a student for wearing a mask, battling Disney over its support of LGBT rights and engaging in strategic spats with the press.

“The Florida governor has figured out that Republicans love a culture-war brawl, but that overdoing it can alienate a general-election electorate. His solution has been to provoke narrowly targeted fights over issues that matter a lot to highly engaged conservatives and liberals — but that will not mean much to anybody else come 2024," the Atlantic’s David Frum argued last year.

Think Trump 2.0, but with less counterproductive tweeting and more hard-nosed governing. "I'm taking what Trump did in 2016, where he broke through and really put the GOP in a great spot," Schweppe said, channeling DeSantis's message. "And I want to build on that. And here's how I'm going to do it. Look at my record in Florida. Look how I think on every issue you care about and was able to actually get legislation passed to start doing things. That's what I'm going to do if I'm elected president."

Some insiders contacted by Yahoo News for this story don’t think that DeSantis — or anyone else — can beat Trump in 2024. And given Trump’s seemingly insurmountable bond with real-life Republican primary voters — who don’t always agree with conservative pundits and professional GOP strategists, many of whom have been rooting for Trump’s demise for years — the odds are probably on their side.

“No battle. Why would DeSantis go against Trump? Makes no sense. He can be a wildly successful two-term governor of the third-largest state and run for president in his 40s,” Kellyanne Conway, a prominent Trump adviser and his 2016 campaign manager, told Yahoo News. “This is not complicated.”

Kellyanne Conway, a former Trump White House adviser.
Former Trump White House adviser Kellyanne Conway. (Anna Moneymaker/Getty Images)

"Ron thinks he can run; I think Trump would absolutely destroy him," added a longtime Republican campaign director who requested anonymity to speak candidly about private conversations with aides from the Trump and DeSantis campaigns. "I think Ron's doing a great job in Florida. Ron’s weird with people. He’s a better governor than candidate for president."

In Trumpworld, the most common refrain about DeSantis is that he doesn’t have the "charisma" for a presidential campaign.

"On DeSantis, I think he would say he's Trump without the abrasiveness," one Trump adviser told Yahoo News. "If he were to use that line of attack, which is what I think he would try to do, I think it would end badly because he's so much more of a jerk than the president ever was."

An extensive New Yorker profile published in June portrayed DeSantis as a pathologically remote figure who is far more comfortable poring over scientific papers than performing the rituals of retail politics: working rope lines, making eye contact, connecting with other human beings. "People who work closely with him describe a man so aloof that he sometimes finds it difficult to carry on a conversation," the magazine reported.

"You will be in the car with Ron DeSantis, and he’ll say nothing to you for an hour," a Republican donor once told Politico. "He would prefer it that way."

DeSantis holds a press conference in Miami.
DeSantis holds a press conference in Miami in January. (Joe Raedle/Getty Images)

Yet so far, DeSantis's charm deficit hasn't halted his rise — perhaps because he has figured out that combativeness plays even better on Fox News, where at times he has appeared at the astonishing rate of nearly once a day and where producers "see him as the future of the party," according to internal emails obtained by the Tampa Bay Times.

As for waiting his turn? Strategists say that history tends to favor those who strike while the proverbial iron is hot.

"Timing is so important in politics," said DuHaime. "Many thought Obama went too soon, only having been in the Senate for a year. But he was the right candidate for the right moment and won."

Schweppe concurred. "[Former New Jersey Gov.] Chris Christie was probably the favorite to win the 2012 GOP primary," he said. "But he made a practical decision; he thought Obama was likely to win a second term. Then he didn't have the same gravitas in 2016. So your moment could be really fleeting."

And even if DeSantis doesn't end up defeating Trump, Cohen argued, he "should [still] run now" if he wants to be next in line.

"Trump is unlikely to win in 2024, despite Biden’s low ratings," the pollster says. In that case, "DeSantis could conceivably run again in 2028."

His message next time around?

"I told you so."

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