Trump and DeSantis: Once allies, now in simmering rivalry with 2024 nearing

Washington Post photo by Jabin Botsford.
Former president Donald Trump, left, and Florida Gov. Ron DeSantis each spoke at the Conservative Political Action Conference in Orlando last February.

Donald Trump put his full force behind Ron DeSantis in 2018, rallying with the GOP gubernatorial candidate in his home state of Florida. “My great friend,” Trump said. “A tough, brilliant cookie.”

Four years later, Trump has yet to endorse DeSantis as he seeks a second term and is unlikely to campaign for him, according to Trump advisers with knowledge of the former president’s intentions. The two men once spoke regularly, a close Trump adviser said, but, “those days are gone.” The two haven’t talked since early in the summer, people familiar with the matter said, and DeSantis has not asked Trump to campaign for him.

A favorite to win re-election, DeSantis is trying to assert his nationalinfluence, appealing to Trump’s supporters and touring swing states to headline rallies for other Republicans on the ballot this fall, as he subtly distances himself from Trump in speeches, while not explicitly criticizing the ex-president.

Although neither has announced any firm decisions, Trump and DeSantis are widely seen in the Republican Party as potential rivals for the 2024 presidential nomination. The public contrasts and behind-the-scenes tensions reflect how formidable an emerging adversary the Florida governor has become to Trump, even as the 45th president polls far ahead of the pack in a hypothetical primary.

At a recent gathering DeSantis had with a few dozen donors in Arizona, “everyone asked him about 2024,” according to Don Tapia, a donor who attended and who served as an ambassador in the Trump administration. DeSantis, Tapia said, “is building a base with the Trump people,” but, “right now the Republican base is Donald Trump’s base.”

In recently flying migrants from Texas to a liberal enclave, Martha’s Vineyard, DeSantis took a polarizing step that Trump considered as president but eventually scuttled. It drew attention and outrage from Democrats and human rights advocates and delighted the conservative base on an issue core to Trump’s political identity: immigration.

The former president tracks DeSantis’s public appearances and polling numbers, according to his advisers who, like others interviewed for this story, spoke on the condition of anonymity to share private conversations. He has also soured on DeSantis, repeatedly criticizing him and telling advisers: “I made him.”

He’s ungrateful, Trump has said, according to two people close to him. “I knew him from watching Fox, and he’d done a good job about me and other things. He’s an Ivy League baseball player,” Trump has said, explaining his 2018 endorsement, according to a person who has visited his Mar-a-Lago Club and heard him talk about DeSantis. “I don’t understand what happened here. I don’t understand why he doesn’t appreciate me more.”

Trump recently polled a room of visitors at his Bedminster golf club about what they thought of DeSantis, according to a person present for the gathering.

Much can change in two years, as reflected in recent presidential primaries in which early front-runners fizzled out, and the futures of DeSantis and Trump are clouded by several external factors, including the outcome of the Florida governor’s race and multiple legal efforts against Trump and his allies. For the moment, however, Trump is broadly regarded in the GOP as the favorite for the nomination, should he run, and DeSantis is seen as his most formidable prospective competitor.

Trump and his advisers widely expect DeSantis to take him on in 2024, multiple people in the former president’s orbit said. Yet Trump has not been adversarial to the current governor because he is favored to win a second term as a Republican in Florida, and advisers said they see little value in open animosity. Some Trump advisers said DeSantis has tapped into the conservative zeitgeist on cultural issues in a way that Trump did in 2016 but has struggled to do since leaving office. One Trump adviser said is it not in anyone’s interest for the two sides to be fighting right now.

Not long after DeSantis claimed credit for flying migrants to Martha’s Vineyard, Trump took to social media to highlight an article in which a GOP strategist argued it would be risky for DeSantis to challenge the former president. DeSantis and his team took note, with one adviser scoffing that Trump was jealous he didn’t come up with the idea, according to a person familiar with the reaction. DeSantis advisers have said recently that they are willing to risk Trump’s ire, this person said.

DeSantis has declined to rule out running against Trump in 2024, annoying Trump. “Nice try,” he said on Fox News over the summer when asked. According to Tapia, DeSantis responded to 2024 queries at the Arizona gathering with: “I’m governor of Florida, and I’m running for reelection in Florida.”

Taylor Budowich, a spokesman for Trump, said in a statement that “Republican leaders everywhere continue to follow and advance President Trump’s ‘America First’ agenda, including highlighting and addressing the crisis on America’s southern border.” He said “the media would rather focus on fake gossip, because the reality is President Trump is stronger than he has ever been.”

DeSantis’s campaign did not respond to requests for comment.

DeSantis has cast himself as a combative conservative in Trump’s mold, denouncing the media and the political establishment. Running for governor as a congressman in 2018, he released an ad in which he encouraged his daughter to “build the wall” with blocks and his wife declared, “People say Ron’s all-Trump.” He shot up in the polls after Trump endorsed him.

But since then, the former Navy legal adviser has built his own brand while swearing off coronavirus restrictions and vaccine mandates, championing legislation that restricts school discussions of gender and sexual orientation and battling with Disney over their face-mask mandates and other policies he has derided as “woke.”

Rather than focus solely on his reelection in Florida this fall, DeSantis has crisscrossed the country to rally with Trump-aligned candidates, visiting battleground states such as Arizona, Pennsylvania and Wisconsin.

Speaking to top Republican donors earlier this month at an Orlando Four Seasons, DeSantis questioned the effectiveness of the coronavirus vaccine for which Trump has taken credit and said that while Trump and his administration had put up some “good fights” on cultural issues, liberals had been winning for the last “five or ten years.” He raised concerns about the deficit growing in the last three years, some of which Trump was in office.

DeSantis surpassed Trump in fundraising during the first six months of the year, and with more than $177 million raised through early September, his political operation has broken records for a gubernatorial race, according to OpenSecrets, which tracks political donations.

He does not strike me as someone sitting around thinking, I’m not gonna do this because it’s going to annoy President Trump, said Republican strategist Rob Jesmer, speaking of DeSantis.

Trump and DeSantis’s social circles overlap – they were at a Mar-a-Lago wedding and made amiable small talk, according to a person who attended the wedding. So do their donors, adding another layer of complexity to their rivalry.

Billionaire businessman Phil Ruffin – a major Trump donor who shares ownership of a hotel with the former president – gave $100,000 this year to DeSantis’s political action committee. At the same time, DeSantis has attracted some donors critical of Trump, such as Citadel founder Ken Griffin, who has said he never donated to the former president.

There are a lot of establishment Republicans that would come home for DeSantis, said David Jolly, a former Republican congressman from Florida who served with DeSantis and now identifies as an independent. DeSantis, he said, “has adopted Trump’s playbook in Florida and he does Trump-like things . . . but he’s actually arm’s-length from Trump.”

Republican operatives and donors who have interacted with DeSantis said he sometimes struggles to connect with people, and his speeches are often didactic – not dazzling the crowd. It is unclear how his insular orbit would exist in a sprawling presidential operation, some of the operatives and donors said. And some of Trump’s advisers said they expect him to lose his political luster over time.

Trump’s advisers said they see weaknesses in DeSantis that could inform their strategy against him, should they be pitted against one another in 2024. They argue that he’s not tested on a national stage and that he is not a compelling speaker. Some people who have met DeSantis earlier this year described the governor as a poor conversationalist with donors.

Shiree Verdone, a former finance co-chair for Trump’s campaigns in Arizona, said she talks to people “every day that say, ‘Wow I really like Ron DeSantis, I think he would be an excellent president, but you know, if Trump runs and we get the nomination, we’re all in for him.'”

DeSantis donor Dan Eberhart said many in the governor’s orbit are urging him to run in 2024. Eberhart added that advisers to DeSantis have told him the governor believes Chris Christie – the former New Jersey governor who ran unsuccessfully for president in 2016 after seizing the national spotlight years earlier – “missed his moment.”

Some Trump donors have said that, after donating to DeSantis, they got displeased phone calls from Trump urging them to stop supporting the governor and saying he may run against Trump, according to a person who works with donors. The person also said some Trump donors seeking a relationship with DeSantis prefer him as a presidential candidate.

Trump has been active on the campaign trail this year, choosing sides in contested primaries and hitting the trail in the general election. He campaigned for Rep. Ted Budd, the GOP’s Senate nominee in North Carolina, on Friday in Wilmington, N.C.

At rallies, Trump has repeatedly suggested he might run for president again, and he remains hugely popular with GOP voters. But a growing tangle of legal inquiries hangs over his plans: The Justice Department is investigating efforts to block certification of Joe Biden’s 2020 victory, and the attorney general of New York on Wednesday filed a lawsuit accusing Trump, three of his children and executives at his company of manipulating property valuations.

Still, Republican leaders – including DeSantis – rallied around him this summer when the FBI searched his Florida residence to retrieve classified papers, part of a criminal probe into possible mishandling of government documents that Trump kept after leaving office.

Once a regular Trump booster on Fox News, DeSantis has hardly mentioned the former president in his latest rallies. Joining Sen. Ron Johnson (R-Wis.) and GOP gubernatorial candidate Tim Michels in Green Bay, Wis., last Sunday, DeSantis mentioned Trump once while touting the Martha’s Vineyard flights and criticizing liberal-leaning cities that call themselves “sanctuaries” for immigrants.

That was a way to virtue signal against Trump and do all this other stuff, he said. “They’re basically doing it so that they feel good, but they don’t want to actually have to deal with the consequences of the policies that they advocate for all of you.”

While the Martha’s Vineyard move drew widespread praise from Trump-aligned Republicans, Trump’s son-in-law, Jared Kushner, was critical, saying in a recent interview on Fox News he was troubled to see people “used as political pawns.”

Some GOP strategists said the decision to fly migrants to Martha’s Vineyard highlighted how successfully DeSantis has echoed Trump’s approach – and refined it.

DeSantis is every bit as good as Trump is at creating earned media appearances, earned media moments that help him stay in the news and help him appeal to conservative voters, said strategist John Feehery.

At a Trump rally in Youngstown, Ohio, earlier this month, many staunch supporters said DeSantis should be Trump’s vice president first – and struggled to imagine the two running against each other. Some blamed the “left wing media” for hyping up a potential 2024 clash.

John Snyder, a 47-year-old rallygoer from Youngstown, said he would think less of DeSantis if he challenged the former president in 2024: “It ain’t his turn.” Connie Vanasdale, who was visiting from Florida, sang DeSantis’s praises but simply pointed to her embroidered hat when asked who should run for president. “Yes I’m a Trump 2024 Girl Get Over It,” it read.

The question was more complicated for Frank Natale, who stopped to buy Trump gear for his chihuahua named Killer.

Don’t you bash me, he told the woman selling the gear, preemptively, when asked who he wanted to run in 2024.

DeSantis, she guessed.

Trump is my 100 percent favorite, Natale assured her. “However, he has to dump that stolen election grift.” (At the rally that evening, Trump reiterated his false claims, echoed by many Republicans, that the 2020 election was stolen from him.)

Even though we know it was stolen, the woman replied.

Natale explained that his next two favorites were DeSantis and Texas Gov. Greg Abbott, another potential 2024 candidate who has made national headlines for rejecting coronavirus restrictions and first busing migrants to liberal cities. Then, Natale raised a possibility unthinkable to many Trump fans.

He would back DeSantis and Abbott if Trump doesn’t seek the GOP nomination – “or get the nomination,” Natale said.