DeSantis campaign pitches donors on ‘leaner,’ ‘insurgent’ campaign to beat Trump

By Steve Contorno and Kit Maher, CNN

(CNN) — Responding to intensifying concerns among his supporters, top advisers to Florida Gov. Ron DeSantis met with key donors and fundraisers over the weekend in Utah, where they promised a new direction to jumpstart his fledgling White House bid.

During the two-day retreat at a luxury lodge in Park City, DeSantis’ team laid out a plan for a leaner campaign more focused on the candidate’s strengths and vision for the country, a clear acknowledgment that the campaign has struggled with cost overruns and messaging since he entered the race in late May.

In a brainstorming session on Sunday, his campaign also fielded suggestions from donors and bundlers on messaging and debate strategy, including how to best handle former President Donald Trump, ideas for debate one-liners and what to do if DeSantis’ top rival for the nomination doesn’t show up for the first GOP primary debate in August.

The retreat, which was scheduled weeks ago but took on new urgency amid DeSantis’ struggles to break out, was described as part mea culpa, part rallying cry. The roughly 70 donors and fundraisers in attendance heard from campaign manager Generra Peck, pollster Ryan Tyson, political director Sam Cooper and deputy campaign manager Ethan Eilon, who provided a detailed look at the campaign’s early fundraising and messaging troubles and their plan for a turnaround.

Nick Iarossi, a Florida lobbyist and fundraiser close to DeSantis’ political operation, described those in attendance as “from all over the country, high level folks who supported a variety of candidates in the last presidential.”

“Everybody’s attitude was positive,” Iarossi said, “but they know they need to continue to raise more money and we must continue to do better.”

The campaign declined to comment on the donor retreat. In a statement, Peck said DeSantis has run from behind before and has often bucked conventional political wisdom.

“Every time he has been underestimated, written off, or dismissed, he has proven his enemies wrong,” she said. “From winning a stunning upset in his first congressional race to beating Tallahassee insider Adam Putnam in 2018 to bucking the entrenched bureaucracy on Covid.”

For weeks, DeSantis’ political operation attempted to paint him as a frontrunner on par with Trump who could mount a national campaign for the nomination out of the gate. His travel extended well outside of traditional hot spots for a primary campaign, including events in Wisconsin and Oklahoma. For a time, DeSantis and his top advisers considered whether he, too, should skip the first debate if Trump didn’t show up, multiple sources told CNN.

Now, DeSantis’ political operation says it is embracing his position as an underdog. They are calling him an “insurgent” candidate with a heavier emphasis on getting DeSantis in front of voters at more intimate events, especially in early states. “DeSantis is everywhere” is the latest framing. The first debate is now seen as critical for DeSantis to move his poll numbers, which have stalled in the low- to mid-20 percent range, according to several recent national polls. A senior campaign official told CNN that DeSantis always planned to debate and noted that the governor said as much the day after he announced his presidential candidacy.

The change in direction comes after weeks of hand wringing over DeSantis’ failures to attract new support since announcing his campaign two months ago . Republican donors and others invested in finding an alternative to Trump have privately – and sometimes publicly – raised concerns about DeSantis’ insular political operation, which is dominated by the governor, his wife and a handful of devoted advisers who lack presidential race experience.

Over the weekend, donors and fundraisers were given an opportunity to voice suggestions in an apparent effort to appease those concerns.

“A lot of investors have a lot of great ideas. So, the team took note of those, so we can continue to massage and refine them,” Iarossi said.

Cutting costs

The campaign has also acknowledged that it needs to cut costs as fundraising fell short of expectations and expenses have piled up.

DeSantis’ team has told donors and top supporters that the plan is to lean more heavily on “outside organizations,” likely a well-funded supportive super PAC. The committee, Never Back Down, has already taken on an unusually heavy load that includes all of the television advertising and building out a campaign of door knockers and canvassers in early states. Now, they are also expected to host DeSantis events, with the candidate appearing as a “special guest.”

A “leaner, meaner” approach is the emphasis going forward after the campaign overextended itself on staff, events and fundraising costs in the first months of the race. The DeSantis’ campaign recently cut at least 10 employees after payroll costs hit $1 million and recent events have been held in smaller venues with a significantly scaled back security blueprint.

The campaign will adopt an approach with more town hall style events “where it’s just him and the voters,” Iarossi said.

“If things aren’t creating a rate of return for us, we’re going to jettison those quickly,” Iarossi siad. “Things that are creating a good return on investment for us, we’re going to double down on but, you know, going forward, that’s going to happen much quicker – much more quickly and much more nimbly than it has this first quarter.”

Advisers have told donors that DeSantis will not pull back on his schedule as the campaign seeks to reign in costs. But that leaves questions about one of the largest expenses on DeSantis’ first quarter fundraising reports: private travel.

DeSantis’ campaign has paid nearly half a million dollars in travel expenses to a company that didn’t exist until two days before he launched his White House bid. The company, N2024D LLC, doesn’t appear to operate private jets or rent buses. Instead, its “managers,” listed on state business documents, work for a Georgia-based firm that has assisted hundreds of federal campaigns with compliance paperwork.

But it does serve another purpose – shielding from public view how DeSantis is getting around the country. The campaign paid the company $480,000 in two lump sums, an arrangement that conceals DeSantis’ mode of transportation and whose plane he might have used.

DeSantis’ preference for private jets is well known among Republican donors and operatives. His wealthy backers often loaned their private planes for DeSantis to jetset around the state and country as governor. Since 2018, a state political committee reported dozens of in-kind donations totaling more than $400,000 itemized as “travel.”

Such an arrangement is convenient in Florida, where there are no limits on what someone can donate to a state political committee, but much harder to replicate in a presidential campaign governed by more stringent contribution limits of $3,300.

As he prepared to enter the presidential race, DeSantis prioritized keeping his travel secret. He signed a new state law that blocks records about his movements from Florida’s robust public disclosure law. DeSantis declined to disclose who paid for a luxury jet to carry him and his family on an international trade mission earlier this year – and later signed a bill that axed the state agency that orchestrated the travel. During a national tour for his new book, some of the travel was arranged by a non-profit with fewer and less timely disclosure requirements.

On May 19, the person behind a Twitter account that publicized flight records for Tesla CEO Elon Musk’s private jet launched a similar account tracking the whereabouts of the governor’s state plane. The next day, the New York Times published an extensive report raising ethical questions about his travel arrangements.

Two days later, N2024D launched, using a name identical to a tail number reserved in 2022 by Scott Wagner, a Miami lawyer and close political adviser to DeSantis.

DeSantis’ campaign did not respond to questions about N2024D and his private travel, instead sharing a previously released statement from spokesman Andrew Romeo that emphasized the campaign would be more “nimble and candidate-driven” going forward.

A Republican fundraiser close to DeSantis’ political operation did not expect the governor and his wife would find new avenues to pay for his travel before forgoing the convenience and comfort of private planes.

New message, same messenger

His advisers have telegraphed that DeSantis in the coming weeks will focus less on his Florida policy victories and more on his vision for the country. They have also suggested DeSantis will return to the hard-charging style that made him a Republican rising star.

It’s unclear how DeSantis will navigate those seemingly contradictory edicts. In his appearances last week in South Carolina, DeSantis delivered a familiar stump speech and unveiled another priority targeting “wokeness” in society, this time aimed at the military. Later in the week, DeSantis announced on Fox he would use the state pension fund to potentially launch a legal fight with Bud Light over its marketing partnership with transgender activist Dylan Mulvaney.

The latest DeSantis salvo in the culture wars drew criticism, and not just from Democrats. Fox host Laura Ingraham offered DeSantis some unsolicited advice during a monologue last week.

“Have fun out there. Don’t be afraid to show your personality, and ask the people what’s on their minds,” Ingraham said. “I promise you, it will not be Disney or Bud Light.”

The campaign hopes to get DeSantis in front of new audiences that he has often eschewed, including through more one-on-one interviews with national media and by taking more questions from reporters at his events. In guidance to some donors and supporters, the campaign foreshadowed that they expect these interactions to show DeSantis’ “fiery” side.

However, that, too, comes with potential pitfalls. At a press conference in Utah on Friday, DeSantis struggled to explain new guidelines for teaching history in his state, which call for middle school students to learn that some enslaved people learned skills that they benefited from later in life.

DeSantis first deflected responsibility to his appointees on the State Board of Education, telling reporters, “I didn’t do it. I wasn’t involved.” Then, attempting to explain the purpose of the benchmark clarification, DeSantis said, “They’re probably going to show some of the folks that eventually parlayed, you know, being a blacksmith into, into doing things later in life.”

The remark drew widespread criticism for DeSantis, including from others vying for the Republican nomination.

“It is shocking to me, Kaitlan, that in 2023, I have to say this. There is no, there was no upside to slavery. Slavery was not a jobs program,” Former Texas Rep. and GOP presidential candidate Will Hurd told CNN’s Kaitlan Collins on “The Source.” “Ron DeSantis showed his lack of leadership by acting like it was somebody else’s fault and not something that was done on his watch.”

Miami Mayor and Republican presidential candidate Francis Suarez, meanwhile, told CNN’s Abby Phillip that he “can’t imagine how you could extol the virtues of slavery,” adding, “I think the governor should have taken that opportunity to demonstrate leadership.”

This story has been updated with additional information.

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CNN’s Aaron Pellish contributed to this report.