Inside the breakup between former allies Donald Trump and Ron DeSantis as the 2024 election grows closer
SAUL LOEB/AFP via Getty Images
- Trump first mentioned DeSantis on Twitter almost 11 years ago.
- His 2018 endorsement helped DeSantis become governor.
- Fast forward to today, and the two are the most prominent Republicans in America.
Former President Donald Trump regularly reminds reporters and confidants that he thinks he "made" Florida Gov. Ron DeSantis.
It's a story that most people following politics have heard by now. Back in 2018, when DeSantis was a little-known congressman whose district included St. Augustine, it was Trump's support that got him elected.
But what's less well known is the more nuanced undercurrents over the years, including how DeSantis, early in his career, frequently sought support from other politicians. When DeSantis was in the Florida governor's mansion, and Trump was in the White House, the two collaborated on several policies. Once Trump was out, DeSantis more aggressively began burnishing his own brand but still frequently drew comparisons to Trump.
As the saying goes, the student became the master.
By the 2022 midterms, DeSantis ran unapologetically on his own record, leaving Trump behind. Should DeSantis choose to run for president in 2024 (and most assume he will, he would need to make the case for why voters should choose him instead of Trump. That's already starting now that the two are feuding more openly.
The sparring is one of the biggest stories in politics, and it has all been more than a decade in the making.
Scroll through to see how the Trump-DeSantis relationship evolved over the years — and how it turned sour.
REUTERS/Carlos Barria
The Trump-DeSantis relationship goes back about 11 years, before Trump even ran for president.
The real estate mogul and reality TV star found himself paying attention to a 33-year-old candidate for the US Congress in Florida — his name was Ron DeSantis.
At the time, DeSantis wasn't well known. He even had to self-publish his own book, which wasn't a memoir but an attempted takedown of former President Barack Obama and the Affordable Care Act, his signature healthcare law.
DeSantis had served as a federal prosecutor and gotten married at Disney World to Jacksonville TV host Casey DeSantis in 2009. Now, as a Tea Party candidate, he was making his first run for office.
DeSantis' resume as an Ivy League graduate and veteran caught Trump's attention.
—Donald J. Trump (@realDonaldTrump) March 20, 2012
"Whether or not Trump comes out and officially endorses DeSantis in his race, DeSantis should consider this a feather in his political cap, since 'The Don' does not give out too many compliments like this," journalist Javier Manjarres wrote on the now-defunct conservative blog The Shark Tank.
DeSantis appeared to understand early on in his political career that one way to get elected was to get more well-known people to support him, particularly in a seven-person primary.
By the time the primary election rolled around, DeSantis could count top Republicans and key groups in his corner. Among them were Ambassador John Bolton, Sen. Mike Lee of Utah, Club for Growth PAC, FreedomWorks, Florida CFO Jeff Atwater, Sheriff Joe Arpaio of Maricopa County in Arizona (who would later get a pardon from Trump), and Erick Erickson from RedState.
During the general election against Democrat Heather Beaven, he got the endorsements of Sen. Marco Rubio of Florida, former Florida Gov. Jeb Bush, Florida Attorney General Pam Bondi, and the National Rifle Association. He even landed a hit on Fox News' Sean Hannity ahead of Election Day.
DeSantis would go on to serve three terms in the US House, representing Florida's 6th congressional district and becoming a founding member of the Freedom Caucus.
Brendan Smialowski/AFP via Getty Images
By 2016, Trump was the one who was running for office for the first time.
The billionaire stunned many politicos when he won the 2016 GOP nomination. He was a Washington outsider whose brash approach turned off many voters, and few national news outlets took his candidacy seriously.
But his populist message and the sheer number of other Republicans who ran for the nomination allowed Trump to gain a plurality of voters.
Not all Republicans were pleased, but most fell in line. DeSantis, who was still a US congressman at the time, was among them. Yet he shied away from issuing a statement that was an outright support of Trump.
His statement read more like a resignation that Trump would face Democratic challenger Hillary Clinton, though he called for voters to unite to defeat her.
"In light of the exit from the race by Ted Cruz and John Kasich, it is now clear that Donald Trump will accumulate the delegates necessary to be nominated by the Republican Party," DeSantis said in a statement, according to NPR. "If we want to defeat Hillary Clinton and have a chance to change the trajectory of our country, we need to unite behind the Republican ticket this November."
At the time, DeSantis was running for the US Senate, but he soon dropped out. The seat he was after was held by Rubio, who lost the 2016 presidential nomination and decided to run to keep his seat after all.
Paul Hennessy/SOPA Images/LightRocket via Getty Images
DeSantis appeared to publicly embrace Trump's presidency soon after Election Day.
Roughly a month after Trump stunned the world by winning the presidency, DeSantis teamed up with Cruz to introduce a bill on congressional term limits — heeding Trump's call to "drain the swamp." (Cruz would later break his own position on the issue by announcing his run for a third term in 2024.)
Going even further, DeSantis also introduced the Drain the Swamp Act in 2017, which he said answered Trump's call to ban officials from lobbying the federal government for five years after holding office.
DeSantis himself was gaining more national attention around this time. This was partly because he told his aides he wanted to be on Fox News as much as possible, Insider previously reported. Often, he talked about Trump.
"The media is definitely trying to sow doubts about Donald Trump's legitimacy," DeSantis told Neil Cavuto in December 2016. "I don't think there's any question about that. I'm not sure that that's necessarily going to have legs. I mean, he is going to take the oath of office on January 20th. And he is going to pursue policies."
DeSantis soon became a network favorite by railing against special counsel Robert Mueller's investigation into Russian interference in the 2016 election. He also introduced legislation to limit the timeline for Mueller's investigation into potential collusion with the Trump campaign.
Trump, known to be an avid cable news watcher, noticed that DeSantis would defend him publicly — it's something he still brings up today.
Lynne Sladky/AP Photo
After almost three terms in the US House, DeSantis set his sights on the governor's mansion.
Trump left DeSantis in suspense after he sought his support.
DeSantis and fellow Florida Republican Rep. Matt Gaetz thought that the president's backing was sealed during an Air Force One ride, Politico reported at the time. The White House then denied that Trump would be involved in the race. But just three days before Christmas in 2017, DeSantis got what he wanted.
"Congressman Ron DeSantis is a brilliant young leader, Yale and then Harvard Law, who would make a GREAT Governor of Florida. He loves our Country and is a true FIGHTER!" Trump wrote on Twitter.
DeSantis was 39 at the time and hadn't yet formally declared he'd run for governor. Six months later, Trump again tweeted his support.
Today, Trump describes DeSantis as having "begged" for his endorsement, telling Hugh Hewitt in February that DeSantis had tears in his eyes — a dubious portrayal given that DeSantis is notoriously unemotional.
Before Trump got involved, DeSantis' main challenger, Agriculture Commissioner Adam Putnam, had done everything right. He was better known and had even endorsed DeSantis for Congress in 2012. He first ran for the Florida legislature as a 22-year-old. After decades in politics, he was the most well-funded challenger and carried a list of key endorsements.
Ron DeSantis campaign
DeSantis embraced the Trump endorsement, and The Palm Beach Post would go on to describe his gubernatorial bid as a "Trump-themed campaign."
Donald Trump Jr. appeared at at rally with DeSantis in central Florida ahead of the primary election, as did Trump himself.
And Casey DeSantis appeared in a campaign ad for the first time.
She cut a humorous ad that aimed to showcase DeSantis as husband and father, while hammering home to voters that Trump had given the congressman his blessing.
"Everyone knows my husband, Ron DeSantis, is endorsed by President Trump, but he's also an amazing dad," she said. "Ron loves playing with the kids." The camera cut to Ron playing blocks with his daughter Madison and saying, "Build the wall," then reading to his infant son, Mason, from "The Art of the Deal."
"People say Ron's all Trump," Casey concluded. "But he's so much more."
Ron told Dagen McDowell on Fox Business Network that he saw the ad as a way to introduce voters to his children and to Casey DeSantis, whom he called "my best friend and best supporter."
As Insider reported in November, the spot was designed to do what Trump himself did best: enrapture, enrage, grab some headlines, and trigger the libs. It worked.
"Ron DeSantis has released an ad indoctrinating his children into Trumpism" read the Guardian headline. HuffPost called it "creepy," and even the libertarian bastion Reason labeled it "cringeworthy."
But by now, most Americans have heard how the story of the primary ends. Trump's endorsement allowed DeSantis to build a campaign around the president's backing. Putnam started the race with a double-digit lead, and his allies hammered DeSantis with tens of millions in negative ads.
It didn't matter, DeSantis saw a surge in the polls after Trump's backing. In the end, DeSantis blew out Putnam by a 20-point margin.
"Such a fantastic win for Ron DeSantis and the people of the Great State of Florida," Trump tweeted. "Ron will be a fantastic Governor. On to November!"
Joe Raedle/Getty Images
The general election would prove to be more difficult, creating a referendum in Florida on Trumpism versus progressivism.
DeSantis was up against Tallahassee Mayor Andrew Gillum, a rising progressive star in the Democratic Party. Soon after the primary, Trump attacked Gillum directly on Twitter, calling him a "failed socialist mayor" and accusing him of running "one of the worst & most corrupt cities in USA."
In contrast, Trump wrote DeSantis would "build on" success from then-Gov. Rick Scott, who was term limited out and was seeking a US Senate seat that he'd go on to win.
"I can't think of a candidate in this country who has leaned in more to the presidential endorsement than Ron DeSantis," White House counselor Kellyanne Conway said on Fox and Friends in August 2018. "He will be a reliable supporter of the Trump agenda."
Conway and Vice President Mike Pence appeared at a rally with DeSantis, but Florida Politics reported the crowd was small.
The rallies went better when Trump himself was there, bringing crowds to Tampa, Fort Myers, and Pensacola ahead of Election Day.
"Ron DeSantis, I've known him a long time," Trump said in Pensacola, according to the Tampa Bay Times. "He's a smart guy; he's a great guy. He'll keep your jobs going way up, he'll keep your taxes going way down." DeSantis boasted at the rally that Trump brought large crowds and ticked off a list of the president's accomplishments.
Trump even mentioned DeSantis while rallying in other states, such as Montana.
In the end, DeSantis narrowly won Florida by roughly 30,000 votes, or less than 1 percentage point. Months after the election, police found Gillum inebriated in a Miami Beach hotel, and he withdrew from political life. In June 2022 the Justice Department indicted Gillum on fraud and other charges. He denied wrongdoing.
Drew Angerer/Getty Images
Trump and DeSantis' partnership blossomed over a series of White House visits and presidential trips to Florida.
It began before DeSantis was even sworn in when Trump welcomed DeSantis and other soon-to-be governors to the White House in December 2018. DeSantis sat right next to the president, who was flanked on his other side by then-Gov.-elect Kristi Noem of South Dakota. Noem is also flirting with a possible 2024 campaign.
In total, he came to the White House for at least six public events. On one of those occasions, in the summer before the 2020 election, Trump and DeSantis teamed up to tout their efforts to lower drug prices.
One of the more notable actions was to speed up federal approval to allow states to import certain medicines from Canada, where they are less expensive because the government regulates prices. As governor, DeSantis had already signed a Florida law allowing such action.
"I think the fact that we're standing here today, obviously, Florida we did some groundwork, but really it is a result of presidential leadership," DeSantis said while looking over to Trump, who had welcomed him to the stage to speak. "You're the one who got it done."
Jabin Botsford/The Washington Post via Getty Images
DeSantis has repeatedly tried to avoid giving a direct response to whether he thinks the 2020 election was rigged. Trump has repeated false claims that there was widespread fraud on a scale that altered the election's outcome, a charge even his own senior advisors have doubted.
"I've been asked that a hundred different times. Anyone have a question on the topic of the day?" DeSantis said during a mid-June press conference, per a Politico report.
DeSantis often said the 2020 election went smoothly in Florida, but he still signed new voting restrictions into law in 2022 that established an elections police and stricter voter ID requirements for mail-in ballots.
Ahead of the midterms, the Florida governor did campaign with GOP candidates who explicitly raised claims about election fraud, including Arizona GOP gubernatorial nominee Kari Lake who narrowly lost her race.
Paul Hennessy/SOPA Images/LightRocket via Getty Images and Scott Eisen/Getty Images
DeSantis was quick to condemn the January 6, 2021, Capitol riot, even if he avoided criticizing then-President Trump directly.
"Violence or rioting of any kind is unacceptable and the perpetrators must face the full weight of the law," the governor said in a statement at the time. "The Capitol Police do an admirable job and I thank them for their hard work."
—Ron DeSantis (@GovRonDeSantis) January 6, 2021
A day later, DeSantis reiterated that the scene was "totally unacceptable."
"It was totally unacceptable and those folks need to be held accountable," DeSantis told reporters. "It doesn't matter what banner you're flying under — the violence is wrong, the rioting and disorder is wrong."
As time went on, the governor began to lean more into his criticism of journalists for continuing to ask questions about the riot and Trump's role in fomenting the violence. A year after the attack, he held a press conference in Palm Beach on an unrelated topic, but was ready to speak about the anniversary when Insider asked him about it.
"This is their Christmas: January 6," the Republican governor said in specifically mentioning media organizations based in Washington and New York. "They are going to take this and milk this for anything they can to be able to smear anyone who ever supported Donald Trump."
Alon Skuy/AFP via Getty Images and Scott Olson/Getty Images
After Trump retreated to his Mar-a-Lago estate in Palm Beach, Florida, DeSantis had a clear foil in the White House: President Joe Biden.
During the early days of the pandemic, DeSantis had initially shut down certain businesses in Florida, just as many states did under federal guidance.
But even when Trump was still president and sparring internally with his health advisors, DeSantis had already reopened Florida far sooner than most states, and had taken significant heat from Democrats and even some other Republicans over his choice.
Still, he resisted changing course — and a surge of people began relocating from blue states, such as Illinois and California, to the Sunshine State. By March 2021, Politico Nightly ran a newsletter whose subject read, "How Ron DeSantis won the pandemic."
At every turn, DeSantis worked to make the contrast between himself and Biden clear. He signed bills into law that banned mask and vaccine mandates. Then, he embraced the culture wars, limiting discussions about gender and race in schools, relocating migrants, and even punishing big corporations such as Disney.
To many, his actions were viewed as intended to rally the Trumpian GOP base. He even had a similar adversarial relationship with the press.
But as DeSantis was coming into his own, Trump himself was still fuming over the 2020 election.
Manuel Balce Ceneta, File/AP Photo
With Trump out of office, DeSantis brought in big headlines and big donors. Presidential buzz swirled. Even Trump supporters gathered outside Mar-a-Lago on the first anniversary of January 6 told Insider that if Trump didn't run again then they wanted DeSantis in the White House.
Trump, who wasn't done with the presidency, noticed.
In the last few months of 2021, stories began to leak that Trump was annoyed with DeSantis. Vanity Fair reported in September 2021 that Trump "resents his popularity."
"Part of Trump's irritation with DeSantis is that Trump feels that DeSantis doesn't give Trump enough credit for his rise," the story said, though it also included denials by Trump.
The New York Times wrote in January 2022 that Trump was becoming more heated, telling advisors he was annoyed that DeSantis hadn't committed to stay out of the 2024 presidential race if Trump were to declare. He called politicians who didn't disclose their COVID-19 vaccine history "gutless" after DeSantis declined to share his booster status.
By June of the following year, Trump told the New Yorker that he would win in a primary against DeSantis and took credit for his 2018 victory.
"If I didn't endorse him, he wouldn't have won," Trump said.
DeSantis, meanwhile, dismissed speculation about a presidential run as "nonsense" and remained focused on winning reelection in Florida in 2022.
Win McNamee/Getty Images
As it turned out, DeSantis would forego seeking Trump's endorsement entirely.
After putting his focus on the Hurricane Ian recovery, DeSantis appeared at campaign rallies across the state, bringing in large, supportive crowds — this time he was able to do it without Trump.
Trump would not go quietly. Just days before the 2022 midterms, the unraveling began. Trump, who was touting his hand-picked Senate candidate Dr. Mehmet Oz in Latrobe, Pennsylvania, lit into DeSantis.
"We're winning big in the Republican Party for the nomination like nobody's ever seen before," Trump told a crowd in western Pennsylvania, projecting a tweet on the big screen, per a Tampa Bay Times report. "There it is, Trump at 71%, Ron DeSanctimonious at 10%. Mike Pence at 7 — oh, Mike is doing better than I thought."
Election Day was still days away. It would later become apparent that the GOP would underperform expectations. Trump, much to his chagrin, would also receive a lion's share of the blame. But that night, the former president's attention briefly turned to 2024. It was the first time he'd publicly showed his annoyance with DeSantis, by branding him with a nickname.
At a rally in Miami soon after with Sen. Marco Rubio — one held without DeSantis — Trump did not repeat the nickname. Instead, he encouraged the crowd to reelect the governor but fell short of an all-out endorsement. He revealed on Election Day that he voted for DeSantis.
Lynne Sladky/AP Photo
Ahead of his reelection, DeSantis ran on his own record, ticking off his accomplishments at every campaign stop.
Even the emotional ad he ran featuring Casey DeSantis was different. Once again, she extolled his virtues as a husband and father. This time, however, it was about how he took care of her when she had breast cancer. Trump wasn't the theme anymore, and DeSantis was his own person.
On Election Day, Trump was done holding his fire, telling reporters he would release damning information about DeSantis.
"I know more about him than anybody other than perhaps his wife, who is really running his campaign," he said.
Trump's attacks appeared to have no effect. DeSantis won reelection in 2022 by a historic margin of 19 points. It was a stunning turnaround from the Trump coattail campaign he'd run four years ago.
Trump, who would soon announce his third consecutive White House run, took to Truth Social to unleash many of the criticisms that had leaked before about DeSantis, calling him an "average Republican governor with great Public Relations."
"And now, Ron DeSanctimonious is playing games! The Fake News asks him if he's going to run if President Trump runs, and he says, 'I'm only focused on the Governor's race, I'm not looking into the future.' Well, in terms of loyalty and class, that's really not the right answer," Trump posted on Truth Social.
The former president continued to remind voters that his support helped put DeSantis in the governor's mansion in the first place.
Joe Raedle/Getty Images
DeSantis, fresh off the campaign trail, initially told the press he was focused on Florida and that reporters were the ones trying to play up a feud between he and Trump.
But soon, he would hit Trump more subtly, including pointing to "the scoreboard" of how he did in Florida compared to other Republicans, many of whom Trump backed. In December 2022, he held a press conference in Palm Beach — not far from Mar-a-Lago — with COVID-vaccine skeptics. It was a move that put him to the right of Trump on the issue.
In February 2023, DeSantis praised Libby Locke during a panel about defamation. Locke was lawyer who represented Dominion Voting Machines in its defamation lawsuit against MyPillow CEO Mike Lindell, whom it accused of spreading false claims about its role in the 2020 election.
MAGA-world pounced on social media, and hours later, Trump showed just how far he was willing to go.
The former president called attention to a social media post accusing DeSantis of "grooming" for allegedly drinking with high school students when he was a teacher at a private boarding school. The picture did not make it clear how old the women were, and one was holding a drink in a brown bottle, but DeSantis wasn't pictured drinking.
The New York Times previously reported that several students recalled DeSantis going to parties with seniors where alcohol was served. Some thought that the parties only occurred after the students had graduated.
DeSantis, in his retort, presented himself as taking the high road.
"I don't spend my time trying to smear other Republicans," he said.
Mandel Ngan/AFP via Getty Images
Today, the Trump-DeSantis feud is out in the open.
DeSantis even gave a major speech to influential conservatives right on Trump's property at Trump National Doral on February 11.
Trump himself didn't speak in person at the event, but he surprised the crowd by calling roughly an hour after DeSantis left the stage, as Insider was first to report.
Soon after, he did an interview with American Family Radio in which he told host Jenna Ellis he would see it as "disloyalty" for DeSantis to challenge him for the 2024 GOP nomination.
"Somebody gets you in, you be loyal to that person," Trump said.
Most recently, Trump took to Truth Social to deny a February 12 report in The New York Times that said Trump has been workshopping nicknames for DeSantis such as "Meatball Ron" and "Shutdown Ron."
"All of the Fake News is reporting that I spend large amounts of my time coming up with a good 'nickname' for Ron DeSanctimonious, who is obviously going to give the presidential 'thing' a shot," Trump wrote. "They are all 100% wrong, I don't even think about it — A very unimportant subject to me!!!"
He followed up on February 19, writing on Truth Social that "it would be totally inappropriate to use the word "meatball" as a moniker for Ron!"
Getty Images
Trump doubled down on his attacks against DeSantis over President's Day weekend, nicknaming him "Ron DeSanctimonious" on Truth Social and raising his past positions, when he was in the US House, on privatizing Medicare and increasing the retirement age.
Trump also openly attacked DeSantis during a Club 45 speech on President's Day in West Palm Beach. Over the weekend DeSantis held several talks in other states about law enforcement, and Trump boasted that his crowds were larger.
"I always say, 'Hit your enemy a little bit early,'" the former president said.
—Florida’s Voice (@FLVoiceNews) February 21, 2023
He also told the crowd that he got more votes in Florida in 2020 than DeSantis got in 2022. The difference in the count can be attributed to higher voter turnout during a presidential election. In all, Trump won Florida by 3 points in 2020 while DeSantis won by 19 points in 2022.
—Florida’s Voice (@FLVoiceNews) February 21, 2023
Trump's attack spilled into social media as well. On President's Day he mocked a DeSantis profile in the New York by writer Salena Zito, calling it a "puff piece" and trashing the tabloid, which he's known to read every day in print.
"DeSantis is a RINO who is trying to hide his past," Trump wrote. "I don't read the New York Post anymore. It has become Fake News, just like Fox & WSJ!"
February 21, 2023: This story originally ran on February 18, 2023, and has been updated with more current information.
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