The DeSantis 2028 Shadow Campaign
The DeSantis 2028 Shadow Campaign
He’s running. Still.
RON DESANTIS IS BACK TO RUNNING Florida’s government. But he hasn’t really stopped running for president.
Next month, DeSantis hosts a two-day presidential-donor gathering at the Hard Rock Hotel in South Florida that’s billed as—don’t call it a “fundraiser”—an “Investor Appreciation Retreat.” It’s the latest phase of an image makeover DeSantis started after he officially dropped out of the 2024 race on January 21 and endorsed Donald Trump.
For the past month, DeSantis has hosted one-on-one thank-you calls with donors, small meetings with more of these “investors” in Naples and in Miami, and conference calls with former volunteers.
In a rarity for DeSantis, he’s expressing some regrets, notably about the way his star-crossed campaign and super PAC stiff-armed the national media.
“I should’ve done as much media as I could because the election was directly a reflection of how much earned media each candidate got,” DeSantis told one group, according to a participant who heard the remarks and relayed them on condition of anonymity. (Another source confirmed the substance of the remarks.)
Coming from a politician who isn’t known for introspection or personal accountability, this admission of error was the clearest sign yet that DeSantis is already laying the groundwork for 2028.
THE CONVENTIONAL WISDOM is that, in politics, candidates learn more from their losses than their wins. By that standard, DeSantis just earned a Ph.D. in running for president. During his campaign he was viewed as stiff and unrelatable, so he now posts slice-of-life pictures and social media videos that give glimpses of his everyday life and less-scripted thoughts. While he was campaigning, he was seen to be especially self-centered and ungracious. So now he’s making shows of gratitude to supporters and donors.
Maybe the surest sign that DeSantis isn’t just on a journey of self-improvement but is actively retooling for another run: He’s getting under Trump’s skin.
On Saturday, seemingly out of nowhere, Trump unexpectedly teed off on DeSantis during a speech in Georgia where he called the governor “DeSanctimonious” and “DeSanctus” again. DeSantis didn’t respond. He has an image-makeover to attend to, a state to run, and hundreds of bills to sign after the state legislative session ended Friday.
AT 45, DESANTIS IS AS MUCH in the middle of his life as the middle of his final four-year term in office. He’s eyeing another shot at the presidency while also trying to coexist with his fellow Florida man, Trump, who once praised DeSantis as one of his “warriors” but now seems unable to forgive DeSantis for challenging him. Even Trump’s online MAGA base is routinely at war with the pro-DeSanis Ron Hive on social media.
Roy Bailey, a DeSantis campaign finance chair who’s helping the governor maintain his relationships with donors, said hard feelings will pass with time.
Bailey pointed out that Iowa voters consistently rated DeSantis as their second choice to Trump. And while DeSantis finished a distant second to Trump in Iowa, DeSantis had much more negative ad money spent against him by outside groups ($47.7 million) than was spent against Trump ($22.5 million) or Nikki Haley ($23.6 million). And even so, he finished the contest with far higher net approval ratings than Haley.
“What a lot of people will admire about DeSantis is that when he realized there was no shot and he was up against the Trump buzzsaw, he dropped out,” Bailey said. “People respect that. They believe it leaves him open to being a great candidate in 2028 if he chooses to do that. The fact is, we were up against the Trump buzzsaw.”
DeSantis also seems to think that he might have had a chance if only Trump hadn’t been indicted. “After the indictments, Trump dominated the news cycle,” DeSantis has said to others. “We couldn’t get any oxygen.”
DeSantis also begrudgingly told them he entered the presidential race too late. He waited until late May 2023 even though Trump announced a week after the November 2022 elections and Haley joined the race in February 2023.
Those who understand DeSantis’s style of thinking say they wouldn’t be surprised if DeSantis learns this particular lesson so well that he announces his next presidential campaign before his term as governor ends in January 2027.
A brief aside on Casey DeSantis: There has been some speculation that she could run to succeed her husband as governor of Florida. The people I spoke with in his orbit think this is unlikely. “So Casey is going to run for governor in Ron’s last year and then Ron is going to run for president in Casey’s first year as governor and then, if he becomes president, they’ll live apart for two years and she’ll only serve one term? They’re not the Underwoods,” said one.
A MONTH AFTER DROPPING OUT, DeSantis began his thank you tour and promptly ran afoul of Trump due to a leaked recording of a 30-minute teleconference with Republican supporters who had backed his presidential campaign. Trump’s team took special umbrage with the way DeSantis gratuitously side-swiped Trump co-campaign manager Susie Wiles, a former DeSantis adviser he came to resent and purged in 2019.
“We were often asked if we would ever stop hitting Ron,” tweeted Taylor Budowich, executive director of the pro-Trump MAGA Inc. super PAC, last month. “The standard response became: it stops when he’s fat again. Now that the time has come, I think we’ll reconsider.”
A week later, at a private “investor” meeting in Naples, DeSantis was more circumspect in discussing Trump, according to an insider familiar with the discussion.
“Everyone knows it’s better for DeSantis if Trump loses. DeSantis knows it. Trump knows it. So there’s no point in Ron talking about it,” the source said.
On Super Tuesday, as Trump was blowing Haley out of the race, DeSantis didn’t attend the Mar-a-Lago festivities. Instead, he held a press conference in Miami Beach to tout a tough-on-spring-break-crime initiative.
When asked if he would consider re-entering the race against Trump, DeSantis almost laughed out loud.
“Been there, done that, got the t-shirt, my man,” he smiled.
After his press conference, DeSantis attended another gathering of “investors” in Miami to say thanks to his former (and future?) donors.
“He’s an old baseball player so he knows he struck out, he’s still in the dugout, and he knows there’s another at-bat,” said an adviser, who was not authorized to speak on the governor’s behalf. “Plus, there’s no crying in baseball.”
State Education Commissioner Manny Díaz Jr., a DeSantis appointee who served as an Iowa caucus precinct spokesman for DeSantis, didn’t hesitate to say yes when asked by The Bulwark if DeSantis would run for president in 2028.
“When the smoke clears, after Trump either wins or loses this year, DeSantis is going to still be standing there in 2028,” Díaz said. “He still has two more [legislative] sessions to go. He’s still a national figure and leader on things like immigration. He’s not governing South Dakota. He’s governing Florida. It’s a big state. Everyone pays attention.”
Five days after DeSantis quit the race, he headlined a press conference with Díaz, who said DeSantis had seemed unfazed by the brutal campaign.
“It was like a switch had flipped. He was engaged in the policy. He was engaged in the legislature. It was Governor DeSantis governing,” Díaz said.
With the Friday end of the legislative session, DeSantis plans to have an aggressive travel schedule in-state to boast about tax cuts, an immigration crackdown, more teacher pay, and hundreds of millions of dollars he plans to veto from the just-passed state budget.
In contrast to the political climate in Tallahassee during DeSantis’s 2022 re-election and his presidential campaign last year, this lawmaking session was comparatively light on culture war legislation. Far-right activists and Republicans fumed that the GOP-dominated Capitol didn’t loosen gun regulations and crack down more on voting by mail, transgender identity, and abortion.
“It was the Seinfeld session: a session about nothing,” one top Republican lawmaker quipped of the sense of malaise in the Florida Capitol, rudderless as DeSantis came home midway through session and caught his breath.
DeSantis experienced some mild Republican resistance this session, a potential sign of things to come in his final two years as he once again eyes the road to the White House.
“For the first four years, it was a honeymoon for DeSantis the likes of which this building has never seen,” said one capitol insider who works with DeSantis’s team. “Going forward, the honeymoon is over.”
I don't think Republicans have as short a memory as DeSantis hopes they do.
Yes, he ignored the MSM, but he has a PERSONALITY problem that isn't going to go away.
So just what are Floridians getting out of their GOP overlords that actually helps their major problems? Doesn't sound like they got anything this year, except much ado about nothing.