Gov. Ron DeSantis (R-FL), once a rising star in the Republican Party, is staring down a pair of decisions in 2026 and 2028 regarding his family’s political future that could both run afoul of fellow Floridian President Donald Trump.
Despite a disastrous 2024 presidential campaign, DeSantis, a popular governor, is a rumored candidate for a 2028 run, setting up a likely showdown with Vice President JD Vance.
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However, the term-limited Florida governor also faces more tensions with Trump if his wife, Casey DeSantis, challenges a Trump-backed congressman in 2026 to succeed him in the governor’s mansion.
“DeSantis’s strong conservative record could put him in the mix, but encouraging his wife to run for governor in a proxy campaign against Trumpworld is an unforced error that will significantly hinder his chances,” a former DeSantis aide told the Washington Examiner about his 2028 chances.
With the awkwardness of Florida’s first lady running to succeed her husband and Vance appearing more likely as Trump’s heir apparent, DeSantis may have missed his moment to win the White House.
“He knows that he’s got to appease President Trump in order to even be viable for 2028, and I think that’s what’s happening,” said Angie Wong, a Miami GOP committeewoman and a Florida delegate to the 2024 Republican National Convention.
After dropping out of the presidential race, DeSantis swiftly endorsed Trump, spoke at the Republican National Convention, and used Florida’s resources to help enact the president’s immigration policies, all of which could help him land a higher office in the future.
“It’s very possible that Ron DeSantis is the man in waiting for a big secretary job within the Trump administration,” said Wong. “I think that’s a good move for him. And then he’s a young guy. He’s in his 40s. He can wait. If it’s not 2028, then the next round, right?”
Jason Roe, a GOP strategist with multiple presidential elections under his belt, claimed that DeSantis’s future remains yet to be seen but offered some words of warning after his bungled 2024 campaign.
“I think he and Trump are playing nice publicly. But I think the punishment for challenging him continues to be the Trump White House policy,” said Roe. “I think if he does go forward with trying to have his wife run to succeed him, he risks a real public humiliation and, I think, an undermining of his political potency.”
Although there has been no announcement, Casey DeSantis is a rumored candidate to run for the governor’s mansion, setting up a primary showdown against Rep. Bryon Donalds (R-FL), whom Trump has endorsed.
It would essentially be another Trump-DeSantis battle, which did not go well for the governor the first time around.
“He belly-flopped on the presidential; if he tries to force his wife on the Florida Republican Party, he’s going to look really impotent in his home state, and then I think he will be a man that missed his moment,” Roe warned.
Several other Republican strategists also cast strong doubt that DeSantis could successfully seek the presidency in 2028.
“Anything is possible, but at this stage, it’s highly unlikely because whoever Donald Trump endorses is going to be the nominee,” said Ford O’Connell, a GOP strategist based in Florida.
“Now, two years to this point is a political lifetime, and anything can happen,” O’Connell continued. “He, obviously of everyone not named JD Vance, assuming he’s patched things up with Trump, has got about as good a shot as anybody else. But again, if Trump decides he’s going to endorse somebody and he’s going to do it early, there’s no chance.”
A March survey from Echelon Insights shows Vance with a huge 2028 advantage among GOP primary voters, with 46% support. DeSantis is tied for second place at 7%, along with Health and Human Services Secretary Robert F. Kennedy Jr. and former Gov. Nikki Haley (R-SC).
If DeSantis were to run, the ghosts of 2024 would be hard to shake off.
His campaign and super PAC were routinely dragged down by infighting, embarrassing campaign resets, and a lack of coherent messaging hitting back against Trump’s campaign.
The Florida governor could also appear awkward on the campaign trail and was dragged down by reports that he inserted height boosters in his cowboy boots.
But perhaps the biggest ghost of the 2024 campaign is the millions of dollars poured into DeSantis that came to naught.
Hunter S. Gaylor, co-founder and president of the business consultant company Spencer Pruitt, stressed that DeSantis likely would not have the finances to run a serious 2028 challenge.
“I don’t think he has any chance of running. He’s trying to repair his reputation with Trump to maybe potentially get an endorsement, but it’s going to come down to money,” said Gaylor, also an adviser to New Journey PAC. “On the money side of things. I think he’s exhausted a lot of the donors from the last election, and we saw how brutal that was.”
Never Back Down, the super PAC that essentially operated as DeSantis’s pseudo-campaign, invested nearly $146 million backing the Florida governor, only for him to drop out one week after the Iowa caucuses.
“JD Vance, being vice president, has all of big tech money behind him,” claimed Gaylor, who is based in West Palm Beach, Florida. “He’s got [former CEO of PayPal] Peter Thiel and Palantir [Technologies]. He’s got Elon [Musk]. He’s got all those people, and DeSantis doesn’t.”
There is some evidence that Vance could enter 2028 with a huge financial advantage over any other challenger. Last month, the Republican National Committee named the vice president as the organization’s finance chairman.
The position puts Vance in direct contact with key Republican donors who could back his future presidential run and block other challengers.
Should a key member of Trump’s current Cabinet leave the administration, DeSantis could be in a prime position to replace them.
However, Steven Abramowicz, editor of the Heartland Journal and host of the Heartland Journal Podcast, said that DeSantis may not want the position.
“I don’t foresee somebody as successful as an executive big state like Florida wanting to take the role of a Cabinet member in the federal government,” Abramowicz said. “Now, most of them would say, if the president asks you, don’t say no to the president, so you take that job … but my gut tells me he would be better served to finish out his term as governor and then run for whatever he wants to.”
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Although Wong, the Miami GOP committeewoman, cautioned against the Trump administration keeping the DeSantis family too far away.
“If Trump is smart, he actually needs to give Ron DeSantis or Casey DeSantis a role just to keep an eye on them,” Wong said. “Just to keep them happy flowing and also keep them out of the way. Because Ron DeSantis can cause a lot of trouble here in Florida.”
