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From Palm Beach to Staten Island, DeSantis makes 2024 moves on Trump’s turf

The Florida governor’s show of force this weekend was part of his increasingly open encroachments into the former president’s longtime support base and ideological terrain

Former president Donald Trump and Florida Gov. Ron DeSantis (R). (Gaelen Morse/Reuters; Marco Bello)
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PALM BEACH, Fla. — Four miles down an oceanfront highway from Donald Trump’s Mar-a-Lago estate, more than 100 influential Republicans gathered at a luxe resort this weekend for cigars, cocktails and plenty of face time with the former president’s chief GOP rival: Florida Gov. Ron DeSantis. “WELCOME TO THE FREEDOM BLUEPRINT,” blared a sign welcoming donors, influencers and lawmakers.

They mingled Friday at the Four Seasons ahead of discussions hosted by DeSantis’s political committee on “election integrity,” border security and “medical authoritarianism,” according to an agenda reviewed by The Washington Post. It all unfolded a day after a much smaller candlelight dinner fundraiser held at Mar-a-Lago for the super PAC supporting Trump’s White House bid — a group with less cash than the DeSantis committee in its coffers at the end of last year.

DeSantis’s show of force in Trump’s backyard was part of his increasingly open encroachments into the former president’s longtime support base and ideological turf. The gathering marked the latest step by DeSantis toward launching a bid for president, as he avoids public conflict with Trump but cultivates Trump donors and supporters, visits Trump strongholds and seeks to make his mark on some issues closely associated with Trump.

Trump’s grip on the Republican base is slipping — even among his fans

DeSantis touted his record as governor extensively in remarks to a packed room Friday night, according to an attendee who, like others interviewed for this story, spoke on the condition of anonymity to describe private conversations. The confab here was designed to showcase DeSantis’s record and show it could be applied nationally, people familiar with the event said. That’s an appealing prospect to many Republicans, including some who used to be staunch Trump supporters.

“Most people wish Trump wasn’t running. He’s the best president of our lifetime, but he’s older, and Biden’s older,” said Doug Deason, who once co-chaired Trump’s Texas finance operation and stood in the front row of the East Room of the White House as Trump spoke on election night in 2020. “It’s time for a new fresh face and new blood. I think DeSantis would be great.”

Deason said he plans to host DeSantis in Texas this week and turned down the chance to join Trump’s Mar-a-Lago fundraiser Thursday.

Representatives for Trump’s campaign and super PAC declined to comment for this story. A representative for DeSantis’s political team did not respond to an inquiry.

To some, the DeSantis event — at a hotel where basic rooms often go for more than $1,000 a night and where Republican guests often stay before heading to Mar-a-Lago to see Trump — was a pointed move into Trump territory. One panel looked at how Republican states can take on the federal government when they disagree, while another examined what states can do about security at the U.S.-Mexico border. Yet another session was titled “Florida: Where Woke Goes to Die.”

Speakers included Tennessee Gov. Bill Lee, Oklahoma Gov. Kevin Stitt and Iowa Gov. Kim Reynolds, an influential Republican from an early nominating state who recently appeared with Nikki Haley as the former U.N. ambassador made her first presidential campaign trail swing. Friday’s discussion of the coronavirus included DeSantis, Sen. Ron Johnson (R-Wis.) and Florida surgeon general Joseph Ladapo, who once declined to say if he has gotten the coronavirus vaccine and has advised younger men not to get it, drawing pushback from the medical community.

Sens. Mike Lee (R-Utah), Tom Cotton (R-Ark.) and Rep. Chip Roy (R-Tex.) also spoke, people at the retreat said, and DeSantis’s wife, Casey DeSantis — who is often described as the governor’s closest adviser — discussed her role as Florida’s first lady. Mick Mulvaney, Trump’s former acting White House chief of staff, was there. And a Saturday night panel featured leaders with the Claremont Institute, the conservative think tank that recently announced an expansion to Florida and stood by one of its scholars, the lawyer John Eastman, amid blowback for his role in Trump’s unsuccessful efforts to overturn the 2020 election.

Also present: Adam Laxalt — DeSantis’s former roommate from Naval Justice School and the 2022 GOP U.S. Senate nominee in Nevada — and conservative media figures and online influencers, such as Benny Johnson, whose viral content has helped propel DeSantis’s rise on the right. DeSantis courted some of those same influencers last year with a dinner at the governor’s mansion.

Fox News host Laura Ingraham and activist Christopher Rufo spoke for the final day of programming, attendees said. DeSantis staffer and former spokeswoman Christina Pushaw, who has gained her own large following online, chatted with Laxalt and a few others over drinks following Friday’s events.

Outside Florida, DeSantis has also sought to establish a presence on terrain that was favorable to Trump in the past, while Trump has tried to hold his ground. DeSantis spent Presidents’ Day addressing law enforcement groups in Pennsylvania, Illinois and New York — specifically in Staten Island, the only New York City borough that Trump won in 2016 and 2020 — delivering the tough-on-crime message that Trump made central to his campaigns. Trump blasted out a raft of policy proposals that evening: “President Trump Announces Plan to End Crime and Restore Law and Order.”

Joe Borelli, a New York City councilman and longtime Trump ally, said DeSantis talked about recruiting law enforcement officers in Florida, the state’s crime rate and how it could be a model for other states. He added that the people who attended the event would be happy to vote for DeSantis or Trump. “It felt like a toe in the water,” he said of DeSantis’s visit, “and if I was him, I would have felt well received.”

DeSantis was introduced by former congressman Lee Zeldin, a longtime Trump ally who was the recent Republican gubernatorial nominee in New York, and he mingled with various officeholders and local activists backstage at a sprawling diner in Annadale on the south shore of the island.

The Florida governor is expected to travel to dozens of cities in upcoming weeks, selling his new book and meeting with local Republican officials and donors. How DeSantis connects with voters and donors across the country, particularly those long loyal to Trump, remains to be seen. Polls show the two men in close competition atop the polls of the Republican primary.

Some people who have met with him in recent weeks say he remains stilted in one-on-one conversations and sometimes struggles to make small talk or appear enthusiastic while engaging in the glad-handing critical to winning states such as New Hampshire, Iowa and South Carolina. Other Republicans dismiss criticisms of DeSantis’s retail politics skills or say he’s markedly improved.

Retreat attendees said DeSantis worked the crowd comfortably throughout cocktail receptions and after-dinner gatherings, talking with people at length. One attendee said he seemed like a “different guy” than the DeSantis who ran for governor in 2018, appearing confident in closed-door settings with powerful Republicans.

Trump’s team has recently ramped up his retail stops including at restaurants when he visits states, saying it shows a sharp contrast from DeSantis.

“DeSantis has really worked the culture wars, really worked Fox News, and he is the known quantity right now to people who are being polled,” Republican consultant Susan Del Percio said. But she criticized his debate performance last fall and questioned if he has the temperament to handle pushback.

His early March trip to Texas — one of many stops in his soon-to-launch book tour — was facilitated by Deason, the longtime prominent Trump donor who has met with DeSantis in Tallahassee as well. Tickets for a “fireside chat” start at $500, and about 600 people are expected to attend, Deason said. Also expected to attend the dinner is Roy Bailey, who has been a major Trump donor in the past and sat at the governor’s table during this weekend’s retreat in Palm Beach, according to attendees.

“The big donors are mostly DeSantis or keeping an open mind about things,” Deason said, adding that he believed Trump maintained considerable grass-roots support and vowing to support Trump if he is the nominee. The Texas donor said that he thought DeSantis would defeat Trump in a primary if it was a one-on-one match, and that DeSantis had the best chance of winning a general election against Biden. “I don’t think there is any question he’s going to run,” he said of DeSantis.

Walter Buckley Jr., who together with his wife, Marjorie, was one of the Republican Party’s top donors in 2022 and who backed Trump significantly in 2020, said he would support Trump if he is the GOP nominee. But he said he prefers many other potential candidates, first and foremost DeSantis.

“As long as he’s in the race, I’m right beside him,” Buckley said, adding, “This guy is special.”

DeSantis’s retreat zeroes in on one area where he has sought to draw a contrast with Trump: his response to the coronavirus pandemic. He has touted his opposition as governor to pandemic restrictions and mandates and requested a grand jury to investigate “any and all wrongdoing” related to the coronavirus vaccines produced during the Trump’s administration and which DeSantis promoted earlier in the pandemic. Trump, in turn, has attacked DeSantis over his flip on vaccines.

Advisers to Trump say they believe things will get harder for DeSantis in the coming months, as he faces closer vetting and withering attacks from Trump and others. So far, DeSantis has largely ignored the criticisms and nicknames.

Trump’s residence at Mar-a-Lago has for years drawn donors, media figures and candidates seeking the former president’s blessing, helping turn this South Florida barrier island into a hub of GOP activity. The Palm Beach County GOP draws donors from around the country with its annual Lincoln Day Dinner; it’s been held at Mar-a-Lago since 2013, when Trump was starting to raise his political profile and was known for baselessly questioning Barack Obama’s birth in the United States.

But many of the GOP’s biggest contributors have cooled on Trump since Republicans’ underwhelming midterm performance, as some blame him for elevating weaker general election candidates with his endorsements. Trump’s motivations for making a third White House bid have also come into question among some in the party.

“Unfortunately now he’s running for president of the United States for revenge against the FBI,” Deason opined, citing the agency’s search of Mar-a-Lago last year.

Trump was not invited to another major donor event in recent days: a Texas conference featuring Haley, the first Republican to challenge Trump for the GOP nomination, and other possible contenders, according to a person familiar with the matter.

Trump’s team has contacted some major donors who say they are keeping their powder dry to see who gets in the race, and his small-dollar fundraising has also declined in recent months. His super PAC MAGA Inc. ended the year with $54 million. Trump’s campaign committee ended the year with about $3 million cash on hand.

DeSantis raised more than $200 million for his gubernatorial reelection campaign last year, largely through his state-level committee, Friends of Ron DeSantis, the group behind this weekend’s Four Seasons retreat. The group ended the midterms with about $70 million unused.

Transferring its funds into a super PAC for use on a federal campaign could prompt complaints to the Federal Election Commission, but the regulators’ members are evenly split along party lines and often deadlock on enforcement.

Dawsey reported from Washington.