Inside the collapse of the Trump-DeSantis ‘alliance of convenience’

Backstage at a House Republican fundraiser in September 2018, President Donald Trump heard an urgent plea from his reelection campaign manager, Brad Parscale: They needed to talk about Ron DeSantis.

At the urging of DeSantis’s team, Parscale begged Trump to set aside a public tiff, according to people familiar with the conversation. DeSantis had infuriated Trump by contradicting his groundless claim that month that Democrats were inflating the death toll from Hurricane Maria in Puerto Rico. Trump viewed the remark as a betrayal since his endorsement had just helped DeSantis win the Republican primary for governor of Florida.

Parscale argued that if DeSantis lost his race that fall, it would make it harder for Trump to win the state in 2020. It’s not just for him, Parscale told Trump, it’s for you.

Trump agreed, and their tension stayed below the surface - until this past fall, in anticipation of the Florida governor preparing to challenge Trump for the 2024 presidential nomination.

Now, their emerging rivalry is the latest twist on a years-long public alliance that belied private misgivings and suspicions, according to interviews with more than a dozen people, many of whom were present for key decisions and conversations, and spoke on the condition of anonymity to discuss private interactions. Despite basking in each other’s reflected glow, Trump and DeSantis had a relationship based on mutual advantage rather than genuine closeness - “an alliance of convenience,” in the words of one person who knows both men.

“DeSantis has both used Trump and overtaken Trump in a remarkable way,” said David Jolly, a former GOP congressman from Florida who served with DeSantis and has been critical of both him and Trump.

DeSantis was skeptical of Trump before he won the presidency and made fun of Trump on multiple occasions, according to recordings obtained by The Washington Post and news reports from the time. Later, he was determined to get Trump’s blessing to boost his bid for governor.

Trump once liked how DeSantis defended him on TV and could advance his own political interests in Florida. These days, he sees DeSantis as an impediment to his bid to return to the White House. “He’s a young guy,” Trump has told advisers. “Why would he not wait?”

As some Republicans loudly pin their hopes on DeSantis to overtake Trump as the party’s new standard-bearer, years of grudges and slights are coming to a head as a potentially defining dynamic of the GOP primary. Polls show Trump and DeSantis as the clear early leaders, even as DeSantis has yet to enter the contest.

Both Trump and DeSantis declined to be interviewed for this story. Trump spokesman Steven Cheung said in a statement, “The 2024 campaign is focused on competing in every state and winning in dominating fashion.” He argued that no other Republican “can generate the type of enthusiasm and excitement like he can.”

A representative for DeSantis declined to comment.

The first notable exchange between Trump and DeSantis came during the latter’s 2012 run for Congress. Longtime Trump associate Roger Stone drafted a tweet sent out by Trump that praised DeSantis as “very impressive,” according to a person with knowledge of the situation. Trump at that time was starting to raise his profile in Republican politics by hawking false conspiracy theories about President Barack Obama’s birth certificate. DeSantis’s Yale roommate, Nick Sinatra, had worked on a 2010 campaign with Stone and was responsible for putting DeSantis on Stone’s radar.

By the time Trump launched his first run for president in 2015, DeSantis joined many other elected Republicans in expressing skepticism of him. “A lot of people look at this with Donald Trump and they say ‘What’s going on?’” DeSantis said in a 2015 news conference. “I think a lot of Republicans say, ‘Look, the guy’s not conservative, he’s got all these liberal positions, weird positions, how can these people be supporting him?’ And I disagree with a lot of his positions.”

In speeches to local Republican groups that year, DeSantis joked about Trump refusing to name his favorite Bible verse and vowing to make Mexico pay for a wall on the southern border, according to recordings obtained by The Post. If Trump had created the world, DeSantis quipped in one recorded speech, “He’d have done it in half the time at half the cost, and he would have had Satan pay for it.”

As DeSantis launched a 2016 Senate bid, he downplayed the earlier Trump tweet, which didn’t used the word “endorse,” and said they’d never met. “He didn’t really endorse me,” DeSantis told Politico at the time. (DeSantis later bowed out of the race when Sen. Marco Rubio decided to run for reelection.)

DeSantis repeatedly dodged questions about committing to back Trump during the GOP presidential primary. “You can either run your own race or you can make comments about other races,” he told the Wall Street Journal in March of 2016. One notable moment of dissent came when Trump singled out the Mexican ancestry of a judge overseeing a fraud case against his real estate training program. DeSantis took exception to Trump’s attack.

“Merely implying bias due to a judge’s ethnic heritage is wrong as a matter of principle and legally illegitimate,” he told the Tampa Bay Times that summer.

But Trump’s surprise 2016 election win changed DeSantis’s political trajectory. He considered a bid for Florida attorney general, but saw a path to run for governor as an outsider against Adam Putnam, the establishment-backed agriculture commissioner, according to people familiar with the matter. DeSantis “saw early on that the country was changing and particularly the Republican base was changing as to what they were looking for in a candidate,” one of the people said.

By early 2017, DeSantis was saying privately he wanted to run for governor and thought he could secure Trump’s endorsement, according to people familiar with the discussions. Later that year, DeSantis rode on Air Force One to a Trump rally in Pensacola, Fla., and not long after that, the 45th president gave him a coveted show of public praise: DeSantis “would make a GREAT Governor of Florida,” he tweeted in December.

Trump had felt moved to send the tweet after seeing a clip of DeSantis on Fox News, according to people familiar with the situation. A couple of weeks later, DeSantis announced his candidacy on the same network, reminding viewers in the same breath that “the president tweeted support for me.”

DeSantis was still in a tough race and went to great lengths to secure an official endorsement, according to three former Trump administration officials. He lobbied White House officials. He called Trump’s friends and other power brokers. Ten minutes is all I need, he told one Trump ally, according to the person.

There was also an effort by DeSantis allies to show Trump statements by Putnam that were critical of him. “He even posted up in Palm Beach at one point,” said a former Trump administration official who was lobbied for a meeting.

Trump has suggested publicly that DeSantis was crying and begging for the nod - “tears coming down from his eyes,” he recently told conservative radio host Hugh Hewitt. That’s not what then-chief of staff John F. Kelly remembered. “I recollect him wanting his support,” Kelly said of DeSantis. “I don’t ever remember him crying asking the president for him to support him. That’s untrue.”

Trump’s staff largely opposed endorsing DeSantis, and even Vice President Mike Pence urged him to stay out, praising Putnam, who was a former colleague in the U.S. House, according to aides.

Eventually, DeSantis secured a meeting with Trump in Florida in 2018 without most of his key staff knowing, people familiar with the matter said. Trump liked the way DeSantis defended him on TV and made his endorsement official in June, touting DeSantis’s Ivy League credentials.

With Trump’s backing, DeSantis leapfrogged to a large lead in the polls. The campaign started airing ads touting the endorsement and showing DeSantis encouraging his young daughter to “build the wall” with blocks, and reading his infant son “The Art of the Deal.” The endorsement also unlocked access to major donors and star surrogates such as Donald Trump Jr.

Putnam chafed at the changing tide, quipping to DeSantis in an August 2018 debate, “Having the Trump card is the only card you have - and it’s a big one - but it still means you’re not playing with a full deck.”

DeSantis won by 20 points.

Before long, the tenuous bond between Trump and DeSantis broke. In late August, about a year after Hurricane Maria devastated Puerto Rico, an independent George Washington University study estimated the storm caused almost 3,000 deaths, far above the government’s official figure, 64. Trump dismissed the research as a political hit “done by the Democrats in order to make me look as bad as possible.”

That put DeSantis in a bind, one of his former aides recalled. His team did not want to directly say that Trump was wrong, the aide said, but also knew it was critical to show solidarity with the Puerto Rican community in a tight race.

The DeSantis campaign released a statement saying he stood with the Puerto Rican community and “doesn’t believe any loss of life has been inflated.” News reports of Trump’s displeasure panicked the DeSantis team, which enlisted Parscale to broker a rapprochement. Trump’s top Florida operative from 2016, Susie Wiles, took the helm of DeSantis’s campaign for the final stretch, bringing their worlds closer together.

In the general election, DeSantis faced a new balancing act to manage his association with Trump. Sometimes, he presented their closeness as an advantage: “I’ll be able to walk in to the Oval Office to talk to the president about Florida’s needs, he’s going to listen to me,” he said at one event. Other times, he sought to assert independence: “I’m my own man, I have a record on different things,” he said at another.

Democrats in Florida and nationally were on their back foot against DeSantis, having expected to face Putnam, said one person familiar with their strategy, noting that Democratic opposition research on DeSantis wasn’t fully developed when he won the GOP primary. Trump held two rallies in Florida to boost DeSantis in the final weeks, and he edged out Democrat Andrew Gillum by less than half a percentage point in a difficult midterm for Republicans, due to a nationwide backlash against Trump.

The former DeSantis aide rejected any notion that Trump pushed DeSantis across the finish line as “totally ridiculous.” Trump probably made the race more difficult in the final stretch, the former aide added.

In office, DeSantis grew angry with Wiles, a steely but soft-spoken operative with decades of experience. DeSantis accused Wiles of leaking to the news media and using her position with him to benefit her lobbying clients, according to people familiar with the matter, allegations she has denied in private.

DeSantis publicly ousted Wiles in September 2019 and - along with Trump friend Ike Perlmutter - pushed influential others in the party to cut ties with her, according to people familiar with the matter. She also lost her lobbying firm job and was excommunicated from Trump’s political operation in a phone call by Parscale, according to people familiar with the matter, with Trump advisers pitching negative stories about her to reporters.

Almost a year later as he was locked in a tough reelection race, Trump hired Wiles to his 2020 campaign over the wishes of DeSantis, who urged against it in a private phone call, questioning her loyalty and competence, according to two people with knowledge of the conversation. Trump hired her anyway, arguing she gave him the best chance to win - and angering DeSantis.

Since 2021, Wiles has led Trump’s political organization and has brought in a number of former DeSantis aides to hold critical roles in Trump’s orbit. In 2021, DeSantis’s team unsuccessfully asked the Republican National Committee to remove her as a top consultant in Florida, according to a person familiar with the matter, while a DeSantis ally said the governor’s team raised concerns about Wiles to the organization. The RNC did not respond to a request for comment about efforts to oust Wiles.

“My obligation is to Donald Trump, to make sure he’s the next president. It doesn’t matter to me who or how many opponents he has,” Wiles said in an interview. She declined to comment on her treatment by DeSantis. Wiles has told others it was a scary and painful time in her life.

In 2020, Trump and DeSantis were often in touch to discuss the response to the covid-19 pandemic. DeSantis often annoyed White House staff by talking to Trump directly instead of going through usual channels, according to former White House officials. “He was one of our biggest problems,” one such former official said.

But Trump didn’t appear to mind, praising him to aides for his Yale education and repeatedly noting he was captain of the baseball team. He was also “muscular,” Trump said. DeSantis would also call others in the White House, such as Jared Kushner, directly on their cellphones, according to a Republican familiar with the conversations.

DeSantis pressed the White House for help with Florida’s coronavirus response, according to this person, including pushing for the state to be first in line for coronavirus vaccines given its large elderly population. Another time, Trump publicly floated blockading people from traveling out of a number of northern states during covid - a move that was roundly criticized and soon rejected - after a call from DeSantis, according to another person with knowledge of the situation, who worried about the people coming into Florida.

Privately, the governor also expressed frustration at times with the president’s rhetoric, the Republican familiar with the conversations said, suggesting he was causing unnecessary problems or making unforced errors.

DeSantis came to Washington in April for an Oval Office photo op as part of the rollout for his plan for reopening Florida, and he and Trump heaped praise on each other.

“They were ready at a moment’s notice to get the ventilators wherever” they were needed, DeSantis said of working with the White House.

Trump gave the impression of a strong rapport, offering to hold one of DeSantis’ poster boards. “I’ll be an easel,” the president joked.

After Trump left the White House, he and DeSantis only spoke occasionally.

Throughout 2021, Trump was skeptical to some advisers that DeSantis would actually run for president against him. Wiles, along with longtime Trump adviser Jason Miller, told Trump that DeSantis would take him on. “Would he really do that? It’s not very loyal,” Trump said in one meeting, according to a person who heard the comments. “I made that guy,” he has said privately.

The former president told others he was kind to DeSantis - even giving him the rare honor of letting him introduce Trump.

Trump, who waded into many midterm races last year, did not endorse DeSantis’s reelection bid or appear with him at a rally the former president held in Florida in the campaign’s final weekend. The large crowd at DeSantis’s own event on the same day only further infuriated Trump, according to advisers, and he seethed about DeSantis’s margin of victory.

The ex-president insulted DeSantis at another rally before Election Day, drawing criticism from other Republicans and some of his own advisers. As DeSantis’s landslide victory contrasted with defeat for many of Trump’s highest-profile endorsed candidates, Trump fired off a social media post again claiming credit for saving DeSantis’s career - this time adding a false assertion that he’d sent the FBI and federal prosecutors to stop DeSantis’ 2018 election “from being stolen.”

“That didn’t happen,” Kelly, the former chief of staff, said.

On Trump’s political team, DeSantis is widely seen as the biggest threat. Trump advisers have begun to compile opposition research on DeSantis, and several people close to Trump said he wants to make DeSantis think about whether he wants to get into the race. They plan to paint him as aloof and cold. Trump has watched clips of DeSantis debating, particularly against Democrat Charlie Crist last fall, and has given advisers dim reviews of his skills onstage.

But they have also closely watched the governor’s positive coverage in conservative media, the adulation DeSantis has received from prominent activists, his aggressive effort to build a network of donors and a series of polls that show DeSantis is Trump’s only competitive rival, four advisers said.

Trump advisers say he wants to make it painful for DeSantis to enter the race - and he has repeatedly taken warning swipes.

“We’ll handle that the way I handle things,” Trump said of the potential challenge in a recent interview. “Ron DeSantis got elected because of me,” he said in another. “You remember he had nothing. He was dead.”

DeSantis has mainly brushed off the barbs, contrasting his overwhelming reelection with Trump’s loss. “In my case, not only did we win reelection; we won with the highest percentage of the vote that any Republican governor candidate has in the history of the state of Florida,” DeSantis said in response to Trump accusing him of “trying to rewrite history” on the coronavirus response. But quietly, DeSantis has worked to cultivate some of Trump’s top donors, people familiar with the matter said, and has weighed taking him on more publicly.

And at some point after last August, the famous ad from DeSantis’ 2018 campaign - the one showing him teaching his children to “build the wall” and reading “The Art of the Deal” - disappeared from the governor’s YouTube page.

The Washington Post’s Michael Scherer contributed to this report.