Can a DeSantis ever win another election?

Alex Isenstadt's new book "Revenge" details Trump's deep disdain for his rival and the consequences of poor political timing.

Mar 19, 2025

Much of politics is the mastery of key moments in time and one’s innate ability to sense not just *what* to say and do — but when. What if Chris Christie had run for president in 2012 instead of waiting until 2016? What if Joe Biden had announced his decision to step aside in the fall of 2022 instead of the summer of 2024? What if instead of acquiescing to the GOP budget plan, Chuck Schumer decided to withhold Democratic votes and shutdown the government last week? Donald Trump has proven himself to possess a visceral instinct for providential political timing for much of the past decade, even when he was experiencing the lowest points of his power. Like in 2023, when Florida Gov. Ron DeSantis was the hot option for Republicans itching to move past MAGA. In his new book, “Revenge: The Inside Story of Trump’s Return to Power,” which you can purchase here, journalist Alex Isenstadt (a longtime personal friend and former colleague) details the deep extent of Trump’s obsession with a man who he evidently never felt threatened by, in part because of his gift for political timing and calm when the walls looked like they were caving in. “Is Ron really that stupid to run against me?,” Trump mused to aides, per Isenstadt’s reporting. “Why doesn’t he just wait until 2028?” (Read my write up of the book HERE.)

Later in the pages of “Revenge,” Isenstadt reveals that the former and future president told staffers he would have endorsed DeSantis as his successor if the governor had waited another four years to run for the White House. “Now nobody wants him,” Trump says. “He’s done.”

It’d be witless to take the mercurial Trump at his word that he would’ve actually cut a deal with DeSantis for 2028 if the governor had stood down in 2024 — and there’s no evidence a formal overture was ever made — but this piece of reporting hangs in the air now like a fork in the road dream sequence. What if the gov had surveyed the land, stepped back and waited — instead of embarking on the tantamount task of challenging a former president and getting pummeled in the Iowa caucuses by a 30 point margin? What if.

Let’s play this out a bit. Even if DeSantis took the “wait and save” option Trump still would’ve had a fresh-faced vice president who would be likely be given a leg up over the rest of the onlookers. JD Vance’s GOP primary lead over DeSantis is currently measured at 39 points, with Health & Human Services Secretary Robert F. Kennedy Jr. in a 3-way tie for third. Will Trump stay high on JD? There’s a lot of runway for things to go sideways. Still, news broke Tuesday that Vance will serve as the Republican National Committee’s finance chair — the first for a sitting VP. It’s an envious role that provides him personal access to the nation’s top donors who want to stay in Trump’s good graces. It’s also likely to become a natural funnel for his own political activity when it ramps up after the midterms. “The RNC might as well cancel the 2028 primaries and caucuses at this point,” texted one longtime Republican operator, leaping to the assumption that it’s Vance or bust.

In the near-term, DeSantis is eyeing his wife to carry the torch and solidify his mark on Florida politics. When she was asked about a candidacy recently, she quoted baseball legend Yogi Berra without fully swinging through the pitch. “When you come to a fork in the road, take it,” Florida’s First Lady said. DeSantis then stepped up to bat and devolved into a blur of unmemorable accomplishments his wife could run on. The problem here again is Trump, who has already endorsed Rep. Byron Donalds, a loyalist who is well-liked within the MAGA orbit and would begin a hypothetical match-up against Casey as the front-runner. The larger question for DeSantis & Co. is whether he and his wife would want to stomach another face-off with Trump and his followers, one that is likely to feel a flashback to the 2023 and 2024?

To picture what a 2026 campaign might look like, Isenstadt’s appropriately titled “Revenge” stands as a helpful reminder. As much as DeSantis and his wife might try to soften Trump’s hand for Donalds, there’s no way the sitting president will want to take an L in his homestate in the final midterm of his final term. And the staffers around Trump — who might even loathe DeSantis and his team more than the president — certainly won’t put their arms down even if the Trump incredulously chooses to.

“Betrayal,” Isenstadt writes, “was just about the only prism through which [Trump] saw DeSantis … Trump didn’t just want to stop DeSantis from winning the Republican nomination. He wanted to destroy him and make it impossible for him to run for anything ever again.”

The more dire threat to the DeSantis’ future might be Susie Wiles, Trump’s campaign manager turned White House chief of staff who was spurned by DeSantis after his 2018 gubernatorial victory. Even after Trump had dismantled DeSantis at the outset of 2024, Isenstadt reports that Wiles told people her team wasn’t necessarily done using “the rusty knife on the governor.”