‘A Crazy Old Man Fighting With Himself’: Can Trump Do to DeSantis What He Did to Bush?

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To become president, Donald Trump had to vanquish a Florida governor. To become president again, he might have to do it once more.

The most important story in politics in the coming weeks and months is the potential resorting of the Republican Party in the aftermath of a midterms in which the GOP was widely expected to win big and ended up winning hardly at all. Within this most important story, though, is a most captivating likely mano-a-mano matchup. Trump is going to have to try to do to current Florida governor Ron DeSantis in 2022, ’23 and into ’24 what he did to former Florida governor Jeb Bush in 2015 and ’16.

Here, though, in the first few days of his third real run for the White House, the trouble for Donald Trump is that the Trump of today is not the Trump of 7½ years back, and neither is Ron DeSantis now the same as Jeb Bush was then. In the estimation of aides and advisers to all three men and dozens of insiders, analysts and operatives from Florida to Washington and beyond, DeSantis is arguably stronger than he’s ever been, while Trump is arguably weaker than he’s ever been. So much, in other words, is so different.

Like Bush, yes, DeSantis packs imposing fundraising might, plus the apparent (and increasing) favor of elite consultants, media and money men of the right. But whereas Bush was a colossus in Tallahassee in his prime — “King Jeb,” some called him — he was 62 by the time he started running for president and had been out of office for the political eternity of more than eight years. He was, of course, also the son of a president and the brother of another — his family name less a helpful legacy than an anvil he dragged around in a cycle defined by an angry, anti-establishment bent.

DeSantis, on the other hand, is 44. He went to Yale and then Harvard Law, but he grew up middle-class in the Tampa Bay area suburb of Dunedin. His father installed equipment for Nielsen. His mother was a nurse. And in this year’s elections in which no small number of Republicans were surprising losers, DeSantis was by far the biggest winner, cresting to a second term by an eye-popping 19 percentage points. People who didn’t vote for DeSantis in 2018 clearly voted for him in 2022. If Bush in 2015 was seen as the past, DeSantis now, in the cheeky new nomenclature of Rupert Murdoch’s New York Post, is viewed as “DeFuture.” In his victory speech in Tampa, in which he declared that he and his campaign team had “re-written the political map,” DeSantis stood in front of not the Florida flag but a giant American flag.

It’s tempting, then, to see Trump, not DeSantis, this time around as more of the Jeb Bush — a has-been who’s done but doesn’t know it or doesn’t want to admit it. “He’s dead man walking,” longtime Florida-based, mostly Democratic megadonor John Morgan told me. “He’s lost three elections in a row,” Sam Nunberg, one of Trump’s earliest political advisers before and during his 2016 campaign, told me. “The majority of the country despises Trump,” Nunberg noted, “and the majority of the Republican Party is moving on.” It’s far from only Murdoch’s Post and Fox News and the Wall Street Journal that are blaming Trump for the spate of GOP losses and blaring a shift in preference. Previously supportive elected officials from the Senate to the House and down to the states have begun to edge away as well. Perhaps equally importantly, right-of-center talkers, bloggers and influencers like Mike Cernovich and Candace Owens have openly criticized a man they once lionized. Some of the most up-to-date polling is showing more Republican voters want DeSantis more than Trump.


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