Florida Gov. Ron DeSantis is gaining steam on former President Trump in a would-be match-up for the Republican presidential nomination. 

But even Republicans who want DeSantis to topple a Trump run have privately expressed some doubts about a potential run during the primary and — if he makes it — in the general election. 

Here are some of the challenges DeSantis could face in a 2024 bid:

He’s not warm and fuzzy 

Anyone who has followed DeSantis in recent years knows he doesn’t mince words. In fact, he’s intentionally over the top. There was the time he called outgoing chief medical adviser to the president Anthony Fauci a “little elf” and said someone “should chuck him across the Potomac.” And there was another time he berated a group of high school students for wearing masks at the height of the pandemic.

“You do not have to wear those masks. I mean, please take them off. Honestly, it’s not doing anything,” DeSantis said at a school event in Tampa, Fla. “We’ve got to stop with this COVID theater. So if you wanna wear it, fine, but this is ridiculous.”

Political observers say this sort of sharp-edged banter could hurt the governor in a primary contest, especially in early states such as Iowa and New Hampshire, where voters want to see the more personal side of a candidate. For that very reason, it could be an uphill climb for DeSantis, said Martin Sweet, a professor of political science at Purdue University. 

“They really want those up-close, multiple-times visits,” Sweet said. “Lots of people want to look under the hood and kick the tires. Can he do that low-level persuasion?” 

“DeSantis emotes a lot less than other prospective candidates and might have some trouble,” he added. 

His retail politicking needs improvement

DeSantis won reelection in Florida overwhelmingly this month in part because he’s proved to residents there that he can get the work done. 

When parts of the only bridge from Fort Myers Beach to Sanibel Island were damaged as a result of Hurricane Ian earlier this year, DeSantis had it temporarily rebuilt in record time. But even Republican allies say the governor needs to work on his retail politicking — from campaign rallies to more personal interactions with voters — if he wants to make the leap from gubernatorial candidate to presidential candidate.  

To date, DeSantis has largely appeared on the stump in one mode. “He’s ‘angry guy at the podium‘ all the time,” one Republican supporter said. “It’s always ‘own the libs.‘” 

That may work in a primary, supporters said, but when it comes to a general election, DeSantis might be forced to try a different, more fine-tuned approach. 

He’s never competed on the national stage

With his growing political profile, it’s easy to forget that DeSantis is still a relative newcomer on the national scene. And while he’s hit the campaign trail for Republican candidates in states such as Arizona, Nevada and Ohio, he’s never had to stump for himself outside Florida.

That makes DeSantis something of a wild card when it comes to a presidential campaign. 

“DeSantis has never run nationally before,” Keith Naughton, a veteran Republican strategist, said. “He’s going to do some dumb things at some point.” 

For one, speaking to voters in a state such as Iowa can be remarkably different than rallying supporters in Florida. And then there’s the challenge of building out a national political operation — a task that can be daunting for even the most experienced candidates, but especially for someone who has a notably small inner circle.

Of course, DeSantis is neither the first nor the only candidate who has overcome such a challenge. Prior to launching his bid for the 2016 Republican presidential nod, Trump had never run a serious campaign before. 

“From the polling we’ve seen in Florida, where people know him and recognize him, it tells me that when DeSantis actually starts introducing himself to voters elsewhere, he’s got a lot of room to grow,” Naughton said.

Too hard right

DeSantis’s allies have billed him as a new voice in Republican politics capable of lifting the party out of a rut following lackluster showings in the last three elections.

But he’s taken many of the same hard-right positions as GOP leaders such as Trump, making him a prime target for the same attacks that Democrats have successfully deployed against other conservatives in recent years.

Earlier this year, for instance, he stirred controversy when his administration paid to fly dozens of migrants from Texas to Martha’s Vineyard, the elite Massachusetts resort town, to protest the Biden administration’s approach to border security.

He’s also positioned himself as a key player in the culture wars over his four years in the Florida governor’s mansion. He signed into law a ban on most abortions after 15 weeks of pregnancy and approved a bill forbidding instruction on gender identity and sexual orientation from kindergarten through third grade. 

And while that has endeared him to many conservatives, some Republicans say his record could become a liability when it comes to winning the support of the broader electorate.

“If you actually look at what he’s done and what he’s saying, his positions aren’t all that different from Donald Trump’s,” one Republican strategist who’s worked in Florida politics said. “So I think if we’re going to have a conversation about Trump’s electability, his appeal to the electorate as a whole, there’s gotta be a similar conversation about DeSantis.”

“Personality-wise, I think he comes off as more in control, more restrained. But again, there’s not a lot of daylight between him and Trump when it comes to the issues.”

Timing 

DeSantis is having a moment right now like no other. Some Republicans who don’t want to see Trump win the nomination see the governor as the one who can save them from that reality. They see him as someone who shares Trump’s politics but isn’t Trump. 

But at the same time, some say, the timing for DeSantis may be all wrong. Why should he have to compete against Trump when the road to the nomination could be free and clear in 2028?

“He has everything to lose and nothing to gain,” Sweet said. “Why piss off the Trump base right now?”

But most importantly, Sweet added, “Iowa and New Hampshire are not simply about winning but instead beating expectations.” He pointed to former President Clinton taking second in 1992 and being dubbed “the comeback kid.” 

“Expectations now are sky high for DeSantis, and if he falls short, that could doom what is otherwise an exceptionally promising future,” he said. 

For now, DeSantis has yet to make a final decision on a 2024 run, according to multiple Republican sources. He won’t be sworn in to his second term in the governor’s mansion until January, and he’s likely to wait until after the Florida Legislature’s 2023 session, which runs from March until early May, to make an official call. 

“I think if he does do it, he wants to go into it with some big wins from session,” one Florida Republican said. “And even then, I think there’s still going to be the question of whether this is the right time.”