Trump, DeSantis, and History: Why It’s Too Early To Take Sides


Before anyone can take sides in the Trump-DeSantis 2024 contest, DeSantis has to announce that he’s running.

In 2014, then-congressman Jason Chaffetz (R-UT) assured the world that Mitt Romney “actually is going to run for president [in 2016] … and I think he will be the next president of the United States.” In the months to come, Romney would deny any interest, but this was a lie. When he finally made a decision six months later, opting to stay out, Romney acknowledged that he had put “considerable thought into making another run for president [and] decided it is best to give other leaders in the party the opportunity.”

Prior to removing himself from consideration, Romney took some of the same steps Gov. Ron DeSantis (R-FL) is taking now. He met with donors for the express purpose of funding a 2016 campaign, spoke with potential staff members and went out of his way to keep his name front and center in media chatter.

Ann Coulter, an eventual Trump backer, hoped and expected that Romney would run. Bill O’Reilly, the biggest name in conservative news at the time, agreed with her predictions. Breitbart also joined the speculation, though had the good sense to splash some cold water on the idea.

RELATED: New Poll Reveals Odds For Trump & DeSantis In Head-To-Head Matchups Vs. Biden

Which brings us back to whether DeSantis will even announce, despite the assumption by so many that he will.

Obviously, DeSantis isn’t comparable to Romney in terms of ideology or his relationship with the Republican base, but he’s likely considering a run while demurring publicly. He’s met with donors more than once and, frankly, he’d be crazy not to have thought about it. Every day, dozens of senators and governors, multiple cabinet members and a handful of congressmen put their shoes on while wondering if they should have the footwear preserved for a future presidential library. It’s understandable. Any one of them could be, at a minimum, a future vice president — and DeSantis is no ordinary governor.

Florida has the third-highest state population in the Union, and DeSantis is its enormously popular leader, having won reelection by nearly 20 points in 2022. He’s the only candidate not named Trump to show significant support in 2024 Republican presidential polls and, at 44, is neither too old nor too young to be taken seriously.

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Yet, he has a history problem that might lead a wise man to focus on 2028.

Incumbent presidents rarely lose reelection bids (Obama, Bush Jr., Clinton, Reagan, Nixon, Johnson, Eisenhower and Truman all secured second terms, and Trump arguably did) and DeSantis is facing two (kind of) incumbents in Trump and Biden. Only Bush Sr., Carter and Ford definitively failed to win reelection in the modern era.

Depending on how one counts it, that’s either an 8:4 ratio favoring incumbents or a 9:3 ratio — and DeSantis would have to face that disadvantage twice. Moreover, Trump and Ford’s problems can be chalked up to factors outside of their control (pandemic, cheating, Watergate).

RELATED: POLL: Trump or DeSantis for GOP Nomination in 2024?

To get a real idea of just how hard it is to beat an incumbent, consider the 1976 Reagan-Ford primary. Ronald Reagan, the, popular, charismatic and conservative former governor of an enormous state (starting to sound familiar?) decided that Ford, unpopular and more moderate, was ripe for a primary challenge. The race went all the way to the convention, but Reagan still lost, securing 46% of delegates to Ford’s 52%.

DeSantis is well known, but Trump has all the name recognition in the world, has won nearly every 2024 Republican poll and has four years of experience doing the exact job DeSantis would be trying to get. The donor class doesn’t love Trump, but he’ll still have a lot of money and an army of hard core supporters who might not vote for DeSantis even if he gets the nomination.

Additionally, DeSantis has to ask himself how willing his is to bloody up Trump and get bloodied up by him.

Reagan lost the first six states on the nominating calendar to Ford and only started gaining when he abandoned his famous eleventh commandment (never speak ill of a fellow Republican) and went for the throat. For DeSantis to beat Trump, he has to be willing to call Trump soft (fairly or not) for not finishing the border wall, rip Trump for pushing COVID vaccines (which are unpopular with the GOP base) and get ugly about Trump’s taking criminal law advice from Kim Kardashian.

Trump won’t take that lying down, of course, so conservatives will walk away with a less-positive view of both men. There are still Republicans who despise Ted Cruz (R-TX) for all but withholding support for Trump after Trump won the 2016 nomination and for the things Cruz said about Trump along the way. Does DeSantis want that baggage?

Yet, what if the DeSantis did run? He could win on merit if voters embrace him as a more-reliable version of Trump, and Biden is a vulnerable incumbent if ever there was one. DeSantis would certainly end up as the nominee if Trump had to drop out due to health concerns. Politics waits for no man, and DeSantis is never going to be a bigger deal than he is right now — nor is he ever going to have a more squeaky-clean image. Even if he lost, he could hope to follow the road paved by Reagan, McCain, Romney and others, returning as the frontrunner after being the runner up. He’d also gain the campaign experience that has been vital for many repeat candidates. So maybe, in his mind, it’s worth it.

Of course, the governor could also take a third path — run, but focus on building his case to be Trump’s running mate. But that way is fraught with peril. Trump would still attack him, a losing campaign could lessen his stature and the man Trump picked last time (Pence) wasn’t a former primary opponent.

If DeSantis runs and wins, he’d achieve the biggest upset of incumbency in U.S. history. If he stays out, he has to pray that his star is still shining brightly a long four years from now.

MORE ON DeSANTIS: CNN’s Ana Navarro Says DeSantis Won Because “He Gamed the System”

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