Florida Gov. Ron DeSantis (R) appears, finally, to be ready to enter the presidential race.
DeSantis, who has long been seen as the most serious rival to former President Trump for the GOP nomination, has been running a quasi-campaign for months, backed up by a big-spending super PAC.
But now multiple media reports suggest the Florida governor will enter the race next week.
He is expected to file paperwork making a bid official around Wednesday or Thursday — the days when he has scheduled a gathering of campaign donors in Miami.
Here are the major questions facing DeSantis as he moves toward that declaration.
How aggressively will he attack Trump?
Trump has been blasting away at DeSantis, referring to him variously as “DeSanctus” and “DeSanctimonious,” contending the Florida governor needs a “personality transplant” and asserting he is “dropping like a rock in the polls.”
Those attacks have coincided with a period when Trump has indeed expanded his polling lead over the Florida governor.
DeSantis is confronted with a conundrum many Trump rivals have faced, going back to the 2016 campaign: How hard should he hit back?
For the most part, DeSantis has avoided frontal attacks, instead obliquely drawing a contrast with the soap-opera dramatics that tend to surround Team Trump.
Speaking at a Heritage Foundation event in April, for example, DeSantis said his administration in Florida had been able to avoid getting “consumed in petty controversy or drama or palace intrigue.”
But his attacks have grown sharper of late.
Recently, he affirmed his commitment to the six-week abortion ban he signed in Florida and complained Trump “won’t answer whether he would sign it or not.”
News also leaked this week of a call with donors on which DeSantis contended he could beat President Biden whereas Trump could not.
A New York Times reporter listened to the call and said DeSantis remarked only President Biden, Trump and himself were “credible” candidates to win the presidency in 2024.
“I think of those three, two have a chance to get elected president — Biden and me, based on all the data in the swing states, which is not great for the former president and probably insurmountable because people aren’t going to change their view of him,” DeSantis said, according to the Times.
Once the campaign gets underway in earnest, the key question will be how far DeSantis goes in ramping up those attacks — or whether he is reluctant to alienate the former president’s supporters.
How will he do on the campaign trail?
DeSantis’s entry into the race has been keenly expected for months.
But there is a long history of presidential candidates who fail to live up to the hype. Detractors of DeSantis cite GOP examples from recent presidential cycles including former Wisconsin Gov. Scott Walker, former Minnesota Gov. Tim Pawlenty and former Texas Gov. Rick Perry. All were considered formidable candidates on paper but failed to deliver once the real campaign began.
Complicating the issue further, DeSantis has the reputation of being socially awkward and uncomfortable with small talk — not fatal flaws in and of themselves but potentially perilous in key early states like Iowa and New Hampshire, where voters expect to see candidates up close and personal.
Beyond such superficial problems, DeSantis has made a couple of missteps in recent months. His minimization of the Russia-Ukraine war as a “territorial dispute” was the worst offender in that regard.
Make no mistake, DeSantis is a very serious candidate. But he can’t afford to misfire very often as he tries to defeat a rival who is the dominant figure in his party and leads in national polls by around 30 points.
Do more donors come to his side, or leave it?
Months ago, DeSantis seemed to be picking up steam as the preferred candidate of Republican megadonors — or at least those who had grown cool to constant Trump-related drama.
Ken Griffin, the billionaire founder and CEO of the Citadel investment firm, was one early key booster.
CNN reported in February that investor Jeffrey Yass had given $2.5 million to DeSantis’s state political committee, while billionaire brothers Jude and Christopher Reyes had given $1 million apiece.
But there has been growing disquiet among donors more recently, especially after DeSantis’s backing of the six-week abortion ban in Florida — a position some in the GOP worry could be politically ruinous in a general election.
The New York Times reported Griffin had also been discomfited by DeSantis’s comments on the war in Ukraine and is keeping his options open.
It’s near certain that both Trump and DeSantis will have all the money they need for a prolonged primary battle.
But it would spell trouble for DeSantis if those influential megadonors started looking at other options entirely.
An unusual ad released this week by Virginia Gov. Glenn Youngkin (R) raised eyebrows in GOP circles.
The ad, notably presidential in tone and imagery, seemed to suggest Youngkin’s previous statements appearing to rule out a 2024 bid might be walked back.
Does his appetite for culture war battles help or hurt?
DeSantis has made himself into a national figure in large part by inserting himself into many of the nation’s most divisive topics.
He has leaped into debates over critical race theory, the teaching of sexuality and gender identity in schools, the curriculum of an Advanced Placement course in African American studies, book banning, and abortion.
Perhaps most famously of all, he is in a long-running feud — and high-stakes legal fight — with Disney. The corporation opposed the DeSantis-backed bill that barred instruction in schools on gender identity through the third grade.
DeSantis is fond of proclaiming Florida is “where woke goes to die!”
There is plainly an audience for that kind of politics, as the governor’s emphatic reelection win in November 2022 indicates.
But there is also a fear voters might be hesitant to defect from Trump toward a politician who seems to relish the same kind of abrasive interventions on the nation’s most sensitive topics.
What if he actually wins?
This is the problem DeSantis would love to have.
But it is a potential problem, nonetheless.
If DeSantis were to defeat Trump in the primaries, it seems extremely unlikely that the former president would concede in good grace.
Back in 2016, Trump suggested there was something nefarious afoot as soon as Sen. Ted Cruz (R-Texas) beat him in the Iowa caucuses.
If DeSantis were to be the nominee, he would face a plethora of dangers, including an independent Trump candidacy, a call from the former president to withhold support in the general election, or simply a decision by Trump supporters to stay home in November 2024.
None of them might happen. But any of them would likely doom DeSantis to defeat.