DeSantis’s Challenge: When, and How, to Counterattack Trump

Gov. Ron DeSantis of Florida prizes preparation and the way it allows him to control his political narrative. But suddenly, he was on the verge of going off message.

He had traveled to a Central Florida warehouse this past week to promote a $2 billion tax cut proposal when he was confronted with the inevitable: an especially ugly attack from former President Donald J. Trump that seemed to warrant a strong response.

Mr. Trump had insinuated on social media that Mr. DeSantis behaved inappropriately with high school girls while he was a teacher in his early 20s. As a reporter asked for his reaction, the Florida governor — standing amid kitchen stoves and boxes of baby diapers — inhaled sharply. He straightened the papers in front of him and raised his open palms to interrupt the question.

But instead of slamming the former president, Mr. DeSantis demurred.

“I spend my time delivering results for the people of Florida and fighting against Joe Biden,” he said. “That’s how I spend my time. I don’t spend my time trying to smear other Republicans.”

For months, Mr. DeSantis has pursued a strategy of conflict avoidance with his top rival in the shadow 2024 Republican presidential primary, delaying what is likely to be a hostile and divisive clash that forces the party’s voters to pick sides.

But now he faces the pressing question of how long this approach can work. Mr. Trump, who has spent weeks trying to goad Mr. DeSantis into a fight with rude nicknames like “Ron DeSanctimonious,” is stepping up his social media-fueled assault, even as polls and interviews show that Mr. DeSantis has become the leading alternative to the former president for many voters and donors.

Mr. DeSantis must also decide just how forcefully to counterattack once he engages with Mr. Trump, and whether he has left himself enough room to effectively parry the former president’s taunts and smears without offending his loyal supporters.

Seventeen months before the Republican nominating convention, the future of Mr. Trump’s political movement seems likely to be decided by a battle between the 76-year-old former president, who has redefined the party in his image as centered primarily on grievances, and the 44-year-old governor, who has presented himself as a new and improved heir — younger, smarter and more strategic, policy-focused and disciplined.

Many conservatives who dislike Mr. Trump’s constant dramas, the myriad criminal investigations he is facing and the stain of his efforts to cling to power after losing the 2020 election have put their hopes in a DeSantis candidacy, in a way their predecessors never did with any of Mr. Trump’s challengers in 2016.

Mr. DeSantis has captured the attention of Republican voters and the party’s activist base by leaning into polarizing social issues from his perch as governor of a key battleground state, while so far refraining from attacking Mr. Trump and other potential 2024 rivals. He has instead insisted that he is focused on governing Florida, where the legislative session is scheduled to run from March to May.

But Mr. DeSantis’s above-the-fray posture carries risk. One of the central tenets of the modern Republican Party under Mr. Trump has been the willingness to fight, ruthlessly and tirelessly.

While the Florida governor has successfully portrayed himself to conservatives as a cultural warrior, his actual experience mixing it up with powerful opponents is thinner. He was barely tested last year during his re-election bid, his first since emerging as a national political figure.

In a memorable debate moment, Mr. DeSantis stood by, stiffly staring ahead, as his Democratic opponent, Charlie Crist, demanded that the governor say whether he would serve all four years of a second term. When called upon next, Mr. DeSantis shot off a sharp canned retort, but the exchange left Mr. Crist looking like the more nimble combatant.

Some deep-pocketed Republican donors have privately expressed concern about how Mr. DeSantis will perform when forced to directly engage with an opponent as combative and unbothered by traditional rules of decorum as Mr. Trump.

“No Republican has ever emerged from an exchange with Donald Trump looking stronger, so the natural tendency is to deflect his attacks and avoid confrontation,” said Liam Donovan, a Republican strategist.

“That’s easy to do, and maybe even wise when his barbs are confined to Truth Social,” Mr. Donovan added, referring to Mr. Trump’s social media site, where he has fired off many of his attacks. “The question is what happens when DeSantis finds himself on a debate stage opposite Trump, and G.O.P. voters want to see whether they are getting what they were promised.”

Mr. Trump’s efforts to undermine Mr. DeSantis began with the “DeSanctimonious” nickname as the governor concluded his successful re-election campaign. Many conservatives — who had cheered Mr. Trump’s behavior when it was directed at Democrats — reacted angrily and were protective of Mr. DeSantis.

It was a signal that Republicans might rally behind a single primary opponent to Mr. Trump in a way they did not in 2015 and 2016, when Mr. Trump called Ben Carson “pathological,” comparing him to a child molester, and insinuated that Senator Ted Cruz’s father had been linked to the assassination of President John F. Kennedy.

Since November, despite the criticism he faced at the time, Mr. Trump has periodically hit out at his potential rival, albeit to a relatively small audience. He posted his most recent innuendo about the governor on Truth Social, where he has just under five million followers. And he has insulted Mr. DeSantis in casual conversations, describing him as “Meatball Ron,” an apparent dig at his appearance, or “Shutdown Ron,” a reference to restrictions the governor put in place at the beginning of the coronavirus pandemic.

Mr. Trump’s team has been amassing data about Mr. DeSantis’s actions in response to the pandemic, in part to try to depict him as a phony.

So far, Mr. DeSantis has countered Mr. Trump’s attacks with occasional needling aimed at the former president’s anxiety about being labeled a loser. While Republicans have suffered through three disappointing election cycles with Mr. Trump as the face of the party, Mr. DeSantis won re-election resoundingly in November.

“Go check out the scoreboard from last Tuesday night,” Mr. DeSantis told reporters days after the midterm elections, when he was asked about Mr. Trump’s criticism.

A spokesman for Mr. DeSantis declined to comment. But a person familiar with the governor’s thinking said he was likely to stick with a measured approach. That means that Republicans hoping for a more aggressive stance by Mr. DeSantis, who is said to be keenly aware of how many of his supporters also like Mr. Trump, are almost certain to be disappointed.

“DeSantis has been getting the benefit of an announced presidential candidate — and all the media attention that comes with that — without having to get involved in every dogfight, because he is operating under the auspices of a governor who is doing his job,” said Josh Holmes, a Republican strategist and top adviser to Senator Mitch McConnell, the minority leader.

Taking on Mr. Trump is complicated. Republican rivals have been unable for seven years to thwart his personal attacks or to dissuade an abiding loyalty to the former president among about one-third of the party’s voters.

There is often little room to question or debate Mr. Trump without being cast by him and his allies as a political adversary, or even a traitor to the country. Such slash-and-burn tactics are a staple not just of his political life, but also of his decades-long career in business before his White House tenure.

“I don’t think people fully understand how ruthless he is,” said Jack O’Donnell, a former casino executive who published a book in 1991 about working with Mr. Trump, and who said he faced vicious threats when he did. “He has no boundaries. And when you’re on the receiving end of that, you wonder what’s next.”

It’s unclear how long Mr. DeSantis can steer clear of the former president while both are anchored to Florida, their home state.

On Feb. 21, the super PAC supporting Mr. Trump’s presidential campaign will hold its first fund-raiser of the 2024 election at the former president’s Mar-a-Lago resort in Palm Beach, Fla.

But just days later, Mr. DeSantis will visit the same 16-mile-long barrier island, where he will host a dayslong “issues forum,” a private event for Republican donors and policy experts to meet with the governor and discuss issues that are likely to be central in a presidential campaign, according to two people who insisted on anonymity to discuss plans for an event that has not yet been announced.

That Mr. DeSantis sees no currency in directly taking on Mr. Trump was underscored by the target the Florida governor preferred to aim at this past week.

At a different event, Mr. DeSantis held court for about an hour behind what looked like a replica of a cable news set, sitting in the center like an anchor, with a busy digital background behind him that read “TRUTH” — an echo of the name of Mr. Trump’s website. He excoriated a favored enemy, the mainstream news media, and called for rolling back the free press’s legal protections against defamation suits.

“It’s a really tough situation for DeSantis,” said Tommy Vietor, a Democratic strategist who worked for Senator Barack Obama in his brutal primary race against Hillary Clinton in 2008. “If he starts punching at Trump, he’s going to anger a lot of the people he needs to vote for him.”

But, Mr. Vietor noted, “if you are viewed as weak and cower in response to attacks from Trump, that will be seen as a proxy for how you will be seen as a Republican nominee and how you’ll be as president.”