DeSantis Struggles to Convert Trump Voters in Campaign Reboot

Photo for The Washington Post by Sergio Flores.
Florida Gov. Ron DeSantis (R) during a rally on July 27, 2023, in Chariton, Iowa.

OSCEOLA, Iowa – On his first day back on the trail after shaking up his presidential campaign, Florida Gov. Ron DeSantis took a question here from a voter who, like many of the attendees at his Iowa events, said she was still deciding whom to support.

“Could you just, without putting anybody else down really, tell me two or three things about you that would make me want to choose you over, I think, a really good list of Republican candidates?” the voter, Kathy Kooiker, said.

First, DeSantis offered his “blue-collar” background, working minimum-wage jobs and serving in the military. Second, he pointed to his “record of accomplishment in office,” rattling off legislation to expand school choice, ban abortion, protect gun rights and limit socially responsible investing.

“I don’t consider myself to be an entertainer,” DeSantis (R) concluded, implicitly referencing the polling front-runner, former president and reality TV star Donald Trump. “I’m a leader. And that’s what you get for me, somebody that will deliver results.”

The exchange captured the challenge facing DeSantis here and across the early nominating calendar: convincing Republicans to peel off from the celebrity who is running functionally as the incumbent and has enraptured the party for approaching a decade, and distinguishing himself from a crowded field as the most qualified successor. It also showed DeSantis’s inclination to try to counter Trump’s star power and visceral allure with a whirlwind of wonky, right-wing policy positions – a strategy that some of DeSantis’s own aides now acknowledge is better suited to wealthy donors and extremely online influencers than for many GOP primary voters.

In an interview afterward, Kooiker said she liked DeSantis’s answer but remained undecided. “We got very used to the entertainment level of Trump, when you agreed with him a lot, he was very funny,” she said. “I don’t feel DeSantis was grabbing my attention that way. Probably Mr. DeSantis personally doesn’t appear really gregarious. We don’t need an entertainer in the White House really.”

Two months into his White House bid, DeSantis has had to lay off staff, curb campaign spending, open up more to reporters and embrace his underdog status – planning a reset to refocus on the economy and foreign policy and spend less time talking about Florida, according to people familiar with the strategy who spoke on the condition of anonymity because they weren’t authorized to speak publicly about the matter. The people described a campaign struggling to find a clear, effective message and often in conflict with its allied super PAC, Never Back Down.

“It’s clear the national media has already pre-written Ron DeSantis’ political obituary – just like they did in 2018, during the pandemic, and numerous other times he defied their flawed narrative,” DeSantis spokesperson Andrew Romeo said in a statement Friday. “The media, national polling, nor the political class decide who the Republican nominee is – voters do, and they’re excited about Ron DeSantis’ candidacy and his vision for the Great American Comeback.”

DeSantis – emboldened by his legislative and electoral success in Florida – entered the campaign confident in his political instincts and way of conducting himself, leading to frustration among advisers who found him difficult to persuade, the people said. He shunned extensively edited scripts in favor of improvising his own remarks, lacking the typical form or features of stump speeches.

And despite the campaign reset, DeSantis has maintained a combative posture with reporters over the past week and kept emphasizing culture-war issues, such as defending Florida’s new standards for teaching Black history that say that “slaves developed skills which, in some instances, could be applied for their personal benefit.”

That wording drew rebukes from Black Republicans including Rep. Byron Donalds (Fla.) and Sen. Tim Scott (S.C.), who is also running for president. Scott told reporters at a campaign event Thursday that “there is no silver lining” in slavery. When asked to respond on Friday, DeSantis shot back, “Part of the reason our country has struggled is because D.C. Republicans all too often accept false narratives, accept lies that are perpetrated by the left.”

DeSantis – who spoke Friday night alongside other candidates at an Iowa GOP dinner – is set to deliver an economic address next week in New Hampshire, where he will spend the weekend attending smaller events. Some of his supporters in early states said they don’t see the need for a drastic change in strategy, emphasizing that it’s still early in the race.

“Iowans right now are kicking the tires. I don’t know that he needs to do anything other than what he’s doing to turn it around,” state Senate president Amy Sinclair, who has endorsed DeSantis, said after his speech in Osceola in Thursday. “He’s not Donald Trump dynamic. Who is? But that’s why it’s important to get in front of people and let them ask questions so that they understand that you don’t have to be this larger-than-life personality to do a better job of getting the job done.”

New Hampshire House Majority Leader Jason Osborne, who has also endorsed DeSantis, acknowledged the needle DeSantis has to thread, wanting to remain appealing to Trump supporters while also offering his own pitch as an alternative.

“Unlike your typical candidate, the former president does have this coalition of support that’s very devoted to just him as a person rather than his ideas or an agenda or a vision for the future or anything like that,” Osborne said. “Unlike your typical candidate, you can’t attack anything about him without rubbing these supporters the wrong way.”

Trump has made DeSantis nearly the sole focus of his attacks on the campaign trail. In a radio interview with right-wing host John Fredericks on Friday, he went so far as to suggest that the Florida governor get out of the race for the “good of the party,” predicting that DeSantis would be “superseded by somebody else.”

The DeSantis campaign pointed to his high favorability ratings with Republican primary voters and how many of them are still undecided to argue that there’s room to grow. But the Trump campaign views that same data point as a point in its favor, because voters who like both candidates tend to choose Trump.

“Those who have an opinion of both overwhelmingly choose Donald Trump. That’s where the race is now, and that’s where the race will be in January, period, end quote,” Trump campaign strategist Chris LaCivita said. “He’s trying to run to the right of Trump or he’s trying to be Trump without the baggage – that’s not a message. New Coke fell flat.”

A recent University of New Hampshire survey found DeSantis with 23 percent support in the Granite State and Trump at 37 percent, among likely GOP primary voters. Fox Business polls in mid-July found DeSantis with 16 percent support in Iowa and 13 percent in South Carolina. Polls from Monmouth University found that among Republican voters, DeSantis’s favorability fell from 80 percent in February to 65 percent this month, while his unfavorable ratings tripled from 6 percent to 18 percent. Trump is at 77-18 favorable-unfavorable, little changed from earlier this year.

During a donor retreat in Park City, Utah, campaign manager Generra Peck told attendees that the campaign had spent too much of the money it had raised but that it was changing course, according to one DeSantis supporter.

“Clearly, there have been some missteps in the beginning as far as hiring too much and spending too much,” the supporter said. “That’s the biggest concern. I think at the donor retreat she did a good job of alleviating a lot of concerns by explaining this shift in strategy in spending and acknowledging that it was a mistake and it’s being corrected.”

DeSantis’s latest swing through Iowa coincided with the layoffs this week and the pullback in campaign event spending, leading to a bus tour produced by Never Back Down, a pro-DeSantis super PAC instead. The campaign and super PAC have traded harsh critiques over each other’s social media posts, ads, events and spending habits, leading to multiple instances of the two groups publicly contradicting or undermining each other.

“From Day One, Never Back Down’s mission has been to organize and support the grassroots movement behind Governor Ron DeSantis’ run for president and to effectively communicate the Ron DeSantis story,” Never Back Down Chief Operations Officer Kristin Davison said in a statement. “Our grassroots operation is light-years ahead of everyone else and we remain focused on amplifying his message through door-knocking – having already knocked 1 million doors nationwide – collecting caucus commitments, robust advertising, and hosting events for Governor DeSantis to attend as a special guest.”

Romeo pointed to an earlier statement that said the campaign is “nothing but grateful for groups like Never Back Down that are also working to support this mission.”

But in acknowledging changes to campaign spending, DeSantis rejected the idea that his message or strategy needed rethinking.

“That’s a process part,” he told Sirius XM host Megyn Kelly in an interview that aired Friday. “That’s not about message, and that’s not about getting out there with voters. That’s about how you’re applying resources to the campaign headquarters versus the early states. So that’s been taken care of, but ultimately that is not what’s going to be determinative in the race.”

Some Republican strategists argue that DeSantis does need to start drawing a clearer contrast with Trump.

“Their big problem wasn’t they had too many people. It’s that they have no consistent message and no clear strategy to win,” said Terry Sullivan, who managed the GOP presidential campaign of Sen. Marco Rubio (Fla.) in 2016. “Donald Trump, whether you like it or not, is the incumbent, at least for the nomination. They need to provide a fireable offense and a reason why they are better qualified to do the job. Full stop.”

The persistent attachment to Trump was evident with many attendees at DeSantis’s events around central Iowa on Thursday. Dan Brewer clapped enthusiastically during parts of DeSantis’s speech in Chariton but described himself afterward as “still a Trump man.”

“Trump’s my guy,” he said. “If something were to happen to Trump, then I suppose I’d choose DeSantis, God forbid.”