“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 G3 Box News) 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.”