Signed Letters, Mar-a-Lago Dinners: Trump’s Personal Touch in Fighting DeSantis

When Anna Paulina Luna’s father was killed in a car crash in January 2022, she received notes from two prominent Florida Republicans.

One was from former President Donald J. Trump, a condolence letter that he signed‌, “Donald.”

The second letter came not from Gov. Ron DeSantis, but from his wife, Casey.

The letters meant something to Ms. Luna, who was endorsed by both Mr. Trump and Mr. DeSantis in the House race she won last year. But in the end, she backed Mr. Trump for president in 2024.

“Trump’s operation is personal,” Ms. Luna said in an interview on Capitol Hill, hours before flying to Mar-a-Lago for a dinner with Mr. Trump and the Florida congressional lawmakers who have endorsed him. “You take the time to actually get to know the people you’re going to be working with and that does make a difference.”

The different approaches to outreach underscore Mr. DeSantis’s political weakness as he finds himself in a heated endorsement battle with Mr. Trump.

The personal touch also helps explain how Mr. Trump — despite one criminal indictment and potentially more to come — has continued to increase his support among Republican lawmakers at the expense of one of the nation’s most popular governors.

Furthermore, it reflects a new approach for Mr. Trump, who appears to be playing the political game in a more traditional way than he has in the past.

Mr. Trump has long been considered the Republican favorite and now holds a lead of almost 25 percentage points over Mr. DeSantis in a FiveThirtyEight national poll average.

Mr. DeSantis, meanwhile, has struggled to find his footing as he juggles duties as governor of the nation’s No. 3 state by population with preparations for his first national campaign. Since declaring himself “kind of a hot commodity” last month in an interview with The Times of London, he has drifted further behind in the polls to Mr. Trump.

During that time, he has been criticized by fellow Republicans for referring to the war in Ukraine as a “territorial dispute.” He adopted a tougher tone about Mr. Trump’s arrest in New York after initially dismissing the case because Florida had “real issues” to focus on.

Mr. DeSantis has also had difficulty at times connecting with potential supporters as he has traveled the country on a book tour. At an event this month in Michigan, he irritated some Republicans who said privately that he had spent little time with the crowd at a morning event and left another in the afternoon shortly after posing for pictures.

Those differences have played out as the two men have pushed for endorsements in Congress: Mr. Trump has collected 47, and Mr. DeSantis, a former congressman, just three.

Mr. Trump, according to congressional aides who have fielded calls from Mr. Trump’s team, has run an aggressive and organized effort to gain support from House Republicans.

One of his top political advisers, Brian Jack, worked during the midterms for Kevin McCarthy, the California Republican whom Mr. Trump helped install as speaker. Mr. Jack, along with Susie Wiles and Chris LaCivita, two of the former president’s senior advisers, have used their connections to coordinate the outreach effort.

Ultimately, it is Mr. Trump who closes the deal himself. He has made calls to lawmakers, many of whom he knows after years of providing endorsements and hosting dinners at his Mar-a-Lago club.

In contrast, some members of Congress said they had not heard from Mr. DeSantis until one of his aides reached out to ask for their endorsements. Seventeen of the Republicans who have endorsed Mr. Trump served in the House with Mr. DeSantis, who left Congress after six years to run for governor in 2018.

Endorsements, like political polls, suggest political strength but are not purely predictive. Mr. Trump, for example, had relatively few endorsements when he ran in 2016, but now shows his deep strength within a certain core of the party even as roughly half of all Republican voters still tell pollsters they are interested in moving on from him.

But endorsements from other elected officials help give candidates an air of legitimacy and can help spread a presidential contender’s message in their home districts.

For Mr. Trump, few political institutions better reflect his arc of power inside the party.

“The pendulum couldn’t have swung much further, and this time Trump is the establishment candidate,” said Dave Wasserman, who analyses House races as a senior editor for The Cook Political Report.

As a candidate in 2016, Mr. Trump had no congressional endorsements for the first six months of his campaign and the first two House members who eventually backed him — Chris Collins of New York and Duncan Hunter of California — both resigned after unrelated criminal convictions and were later pardoned by Mr. Trump.

Since then, Republican House candidates have effectively crawled over one another to seek Mr. Trump’s seal.

Mr. Trump’s endorsement advantage is most pronounced among Florida’s 20 Republican House members, nine of whom have already backed him, including Representative Michael Waltz, who succeeded Mr. DeSantis in Congress. Two more Florida House members, Gus Bilirakis and Carlos Gimenez, are expected to announce their support for Mr. Trump in the coming days, according to people familiar with the planning.

Representative Greg Steube of Florida, who was hospitalized for four days after falling 25 feet off a ladder at home this year, told Politico this week that Mr. DeSantis’s office had never reached out to him and also ignored multiple requests to connect. Mr. Trump was the first person to reach out to Mr. Stuebe while he was in the I.C.U., he said.

Representative Vern Buchanan of Florida endorsed Mr. Trump on Wednesday after a personal call from the former president, who asked for the endorsement and extended an invitation to dinner on Thursday at Mar-a-Lago.

Mr. DeSantis has support from one Floridian from Congress so far: Representative Laurel Lee, who served in Mr. DeSantis’s administration.

Ms. Lee endorsed Mr. DeSantis on Tuesday when the governor made a special trip to Washington to meet with members of Congress. But Mr. Trump picked up multiple endorsements just before and after Mr. DeSantis’s meeting — including one from Representative Lance Gooden of Texas, who announced his endorsement of the president within minutes of leaving the meeting with the Florida governor.

Still, Mr. Trump’s power has its limits — even in Congress.

In the 36 most competitive House races during the 2022 midterms, Mr. Trump endorsed just five Republicans — all of whom lost.

More than half of the nearly 50 endorsements he has received have come from members who won their races last year by 30 points or more, or represent such heavily Republican districts that Democrats didn’t field an opponent.

When it comes to the most-watched Florida delegation, Ms. Luna said that most of them want Mr. DeSantis to continue furthering his conservative agenda from the Statehouse.

The ideal situation, she said, was for Mr. DeSantis to hold off on his presidential ambitions until 2028. “If he does announce,” she added, “we’re going to be bummed.”