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

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,” San 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.

Anybody else would acknowledge this bald reality and fade away or at least take a break. But Trump is Trump. And for all the ways he so consistently stokes chaos, Trump, 76, is nothing if not predictable. He won’t let it go because he never has. He won’t admit defeat because he never has. He won’t willingly, much less graciously, cede the spotlight … because he never has — especially not to a seemingly able and ascendant heir. “He can’t accept that anybody else can do what he perceives he can do,” Alan Marcus, a former Trump publicist and consultant, told me. “And he also can’t accept walking away because that would indicate he’s a loser.” And so he’s going to attack DeSantis. He already is. Whether it works — whether he can do to DeSantis what he did to Bush — is very much to be determined. But what is almost certainly to come really is no mystery at all.

“Trump will just fling himself at DeSantis, saying whatever, whenever,” said Mac Stipanovich, the Tallahassee fixture of a Republican operative who now is a registered independent on account of his distaste for Trump. “Anyone who would discount Trump at this point hasn’t been paying attention,” said Alex Conant, a GOP consultant who was a key aide to Marco Rubio during the 2016 presidential campaign. “I would never discount his ability,” Conant said of Trump, “to trample the competition and win the primary.”

“DeSantis’ team is full of smart people,” anti-Trump Republican strategist and Lincoln Project co-founder Reed Galen told me, “but they’ve never faced a face-eating dragon before.”

“Folks forget,” a close Trump adviser told me, “what DJT can do to somebody.”

Trump’s initial taunts were all so long ago — two country-altering presidential elections, two midterms, a world-changing pandemic, an insurrection Trump helped incite — but it’s worth recalling the first time you heard them.

“Crooked Hillary.”

“Lyin’ Ted.”

“Little Marco.”

Trump called (subsequent sycophant) Lindsey Graham “an idiot.” He all but likened Ben Carson (later his Secretary of Housing and Urban Development) to a child molester. “Look at that face!” he said of Carly Fiorina. The list is long. He said and has said lots of nasty things about lots of other candidates and lots of other people.

But what he did to Jeb Bush was different. It was the original article and especially venomous. He didn’t ridicule his policies. He ridiculed him. He called him “weak.” He called him “desperate” and “pathetic” and “sad.” He said he was “not a guy who can be president.” He said he didn’t “have what it takes.” He said he was “an embarrassment to his family.” Above all else, though, and this is of course what stuck the most, Trump called him “low-energy” — “Low Energy Jeb.”

Bush responded, in part, by enumerating for (my now colleague) Jonathan Martin his very busy travel schedule. He expressed a sort of bafflement that was in retrospect somewhat endearing but woefully naïve. He “just repeats it over and over again, it becomes the truth,” he once said of this nickname with which he’d been tarred. “It’s the weirdest thing in the world.” And eventually he tried during debates to go toe-to-toe. “You’re not,” Bush told Trump toward the end of 2015, “going to be able to insult your way to the presidency.”

He was.

He did.

“He got there by destroying those who tried to go against him,” said longtime New York-based Democratic strategist Hank Sheinkopf, who’s been watching Trump for decades. “He cut all his opponents down, one by one, without remorse,” as a former Trump adviser put it to me. “He killed everybody,” Sheinkopf said. “But what he did to Jeb was he emasculated him.”

Why Trump did what he did to Bush with such focus and ferocity was not hard to figure. He said so. “When I first ran, I hit him really hard because I thought he was going to be the guy,” Trump told Insider (which is owned by the same company as POLITICO) in an interview in Trump Tower that first November. “You know, he’s the establishment guy. So I hit him very hard.”

All of this, at least back then, felt shocking. It was also just plain surprising. “And I don’t think you can pull that surprise twice,” reasoned Marcus, the ex-Trump publicist.

“There was a Bush fatigue and Jeb got clobbered by that. There now is a Trump fatigue,” Ed Rollins, the veteran GOP consultant who managed Ronald Reagan’s 1984 reelection campaign and chaired a pro-Trump PAC but now is pro-DeSantis.

“Trump was new and interesting in 2016,” former Florida Republican Rep. Carlos Curbelo told me. “Now he’s become old and predictable.”

“I’ve long said this: People tire of the Trump show,” Allen Salkin, the author of a book about Trump, The Method to the Madness, told me.

“He manages to reinvent time and time again, though,” he said. “Does he have another act in him?”

Past isn’t always prologue, but it almost always is with Trump. And he traditionally has been at his most ferally effective when it looks to many, if not most, like the jig is up and he’s backed into a corner and existential comeuppance seems nigh, and also when he has an easily identifiable and obvious enemy. Check. And check. For Trump, fights and foes are fuel.

Even so, the rise of DeSantis has to smart. Because DeSantis had next to no chance of getting elected governor in 2018 without Trump’s endorsement. He, too, had to beat in a primary an establishment-tapped frontrunner, and he couldn’t and wouldn’t have done it without Trump. One way to see this is Trump made DeSantis, but the more accurate read is that DeSantis, much less viscerally charismatic but much more methodically strategic, used Trump. Trump is “a user of other users,” the late seminal Trump biographer Wayne Barrett wrote more than 40 years ago, and so DeSantis stands as a user of this user of other users. Even people who don’t like him have always said he studies hard. Now Trump is on the downslope, and DeSantis is on the upswing, and Trump appears to know it.

In a pre-midterms rally in Pennsylvania—ostensibly to reaffirm his endorsement of the eventual loser, Dr. Oz — he for the first time called DeSantis “Ron DeSanctimonious.” (It’s no “Low Energy Jeb.”) Last week, after a rally in Ohio — where he wanted to announce already that he was running again for president but was talked out of it by advisers — he floated a DeSantis-directed threat: “If he did run, I will tell you things about him that won’t be very flattering. I know more about him than anybody other than perhaps his wife, who is really running his campaign.” He didn’t congratulate DeSantis on his resounding Election Day win. He pointed out on Truth Social that he got in 2020 more than a million more votes than DeSantis did in 2022. And a day after that he shot off a 478-word statement in which he accused DeSantis of a lack of “loyalty and class.” This is almost certainly only the beginning of the barrage.

To this point, DeSantis has responded by not responding. He could do this for a while. His fresh reelection and its margin, say strategists, earned him more than an uptick in political power. It also bought him time. Trump is antsy. DeSantis is busy. The same day Trump issued his most extended attack on DeSantis, for instance, DeSantis held a briefing on Hurricane Nicole. Florida’s annual legislative session next year runs from the first week of March to the first week of May, and a GOP-controlled, DeSantis-dominated corps of lawmakers is sure to offer him bills to sign ready to be added to early-state stump speeches. Nothing if not disciplined, according to allies and enemies alike, DeSantis could attempt to put into practice some version of what so many people for so many years have talked about in theory. Could he in essence … ignore Trump to death?

“Because then it’s just a crazy old man fighting with himself,” a Florida-based GOP strategist told me. Do it too long and maybe DeSantis starts to look weak. But for now? “If I were him, I’d just keep my mouth shut,” said one former Trump adviser. “It’ll drive Trump a little nuts,” said another.

Plenty of politicos from Florida to Washington and beyond say Trump is the favorite until he’s not. Plenty of others are picking DeSantis even as they tick off what they perceive to be his faults (he’s had but one close race, he can come off as prickly, unlikeable and aloof, his head’s too big and his circle’s too small ...). Some see not another Jeb Bush but another Scott Walker, or Chris Christie, or Tim Pawlenty or Rick Perry — governors who were bandied about as potential presidents but never got close. But the most important comparison — for both Trump and DeSantis — remains Jeb Bush.

Bush “was the perfect foil — a living testament to the political class, a darling of the establishment who had been a successful governor but who could not have been more out of step with what the base was looking for,” Republican strategist Liam Donovan told me. “Whatever you think of DeSantis he is none of that.”

“Jeb was an easier target,” said Doug Heye, another GOP strategist.

“DeSantis is his worst nightmare,” Nunberg said. “Younger, smart and accomplished.”

Then again? “Picture them on the debate stage: DeSantis squat, dour and angry, as Trump towers over him physically,” Stipanovich told me. “DeSantis is not without talents, but agility and improvisation are not among them,” he said. “He is an engineer, not an artist.”

“I’d still give the edge to Ron in a head-to-head, but we are way too early,” said former Florida congressman, and former Republican, David Jolly, “for the coronation some are now declaring.”

Earlier this fall, well before the midterms, the polls flipping from Trump to DeSantis and the announcement at Mar-a-Lago, I was on the phone with Rick Wilson, the Tallahassee-based Republican strategist and Lincoln Project honcho who wrote the book called Everything Trump Touches Dies. We talked about this coming clash. He voiced doubt that DeSantis had it in him to take down Trump but still played out the script.

“Let’s say you beat him. Let’s say you whip his ass so bad in every debate. Let’s say he shits the bed in every debate and DeSantis is articulate and brilliant and funny and does all the things that you would need to do to convince primary voters. Let’s say that happens,” Wilson told me. “What,” Wilson asked, “does Donald Trump do?”

“I know what he doesn’t do,” I said. “He doesn’t disappear.”

“Correct,” said Wilson. And here, he added, is what else Trump doesn’t do: “Donald Trump says, ‘I was beaten, fair and square, by this brilliant young man, Ron DeSantis. I believe that he is the future of our party and our country. I look forward to doing everything I can to ensure that he is elected president in 2024. And because of that I’m turning over my email lists and my political operations to do whatever I can to help him win.’”

I reminded Wilson of this part of our conversation when we touched base last week. “He is a political suicide bomber,” Wilson said. “All Trump has to do is say, ‘OK, you don’t like me? I’m going to run as an independent.’”

Which presumably would make it hard — impossible? — for a Republican, for any Republican, Ron DeSantis or not, to win the White House in a general election.

“Let me tell you something,” Wilson said. “Donald Trump would rather Joe Biden be president for a thousand years than Ron DeSantis be president for five minutes.”