Donald Trump vs Ron DeSantis
Ron DeSantis juggles hot-potato issues. Photo credit: DonkeyHotey / WhoWhatWhy (CC BY-SA 2.0) See complete attribution below.

Donald Trump, and his challengers, make sure that anybody trying to kick the former president off his leading-candidate perch as the Republican leader faces a steep uphill climb.

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UPDATED January 22, 2024 — In the history of primary politics, there may never have been a campaign from a once-promising candidate that was as doomed to fail as that of Florida Gov. Ron DeSantis. 

On Sunday night, he mercifully called it quits, but not before debasing himself one more time by endorsing Donald Trump, who had been mocking the Florida governor every step of the way.

When we say he never had a chance, it isn’t Monday-morning quarterbacking. His failure was always inevitable. In fact, we predicted the the insurmountable challenges DeSantis faced and the idiocy of his presidential bid and its timing right after he announced his candidacy. Instead of becoming the heir apparent to Trump in 2028, he inexplicably squandered his presidential ambitions by betting that Republican voters would prefer an extremely poor copy of Donald Trump to the real thing. Take a look: 

May 28, 2023 — Every couple of years, scores of small-money donors waste millions of dollars on Democratic candidates with no chance of winning, just because they want to take down a certain Republican and are led to believe that their $20 donation can help make that happen. In 2020, for example, Amy McGrath raised and spent over $90 million in an attempt to defeat Sen. Mitch McConnell (R-KY). She lost by almost 20 points.

This year, deep-pocketed Republicans appear set to light an even larger pile of money on fire in pursuit of claiming the biggest scalp in all of politics: Donald Trump’s.

It is easy to see why they want to get rid of the former president. To them, he is a liability. Trump lost the popular vote twice, and, in the last two elections, he cost the GOP a Senate majority. Plus, with his mounting legal troubles, there is no way of knowing whether he will be in or out of prison by November of next year.

There are just a few minor problems with this anti-Trump stance. The first is that, while many in the old guard of the Republican establishment loathe Trump, GOP voters idolize him. Essentially, the challenge is to replace the leader of the cult with someone who is, well, not the leader of that cult.

The second problem is that, once again, the GOP establishment has chosen a Florida governor with little personality as its champion to vanquish Trump. That didn’t work in 2016 when Jeb Bush was the chosen one, and current Gov. Ron DeSantis has given no indication that he is up to the job.

While he likes to portray himself as someone who never shies away from a fight, we have only ever seen him punch down. Obviously, that won’t do versus Trump, who is firmly entrenched atop the Republican heap.

In other words, to beat the former president, DeSantis would have to attack him with the same enthusiasm with which he attacks gay high school students.

And, so far, there is no indication that he wants to get down in the gutter with Trump.

Because, make no mistake, that’s where this fight would take place.

Following the DeSantis announcement, some of the most decorated reporters of the venerable New York Times wrote a piece on “The Policy Fights Where DeSantis Sees His Chance to Hit Trump.”

Here is how it starts:

Ron DeSantis is girding for battle with Donald J. Trump where he believes the former president may be most vulnerable to attack from a fellow Republican: on substance.

Mr. DeSantis, the Florida governor, is expected to make a series of policy-based arguments, according to his public statements and interviews with people who have met with him privately and described their conversations on the condition of anonymity.

“Policy fights”? “Substance”? “Policy-based arguments”?

You would have to be a fool to think that this GOP primary is going to hinge on policy differences. Republican voters in general, and certainly those on the hard right who will decide this race, do not give a damn about policy. They just like it when Trump burns stuff to the ground.

Now, let’s say DeSantis does decide to go after Trump and that he does fight him as hard as he fights Florida teachers who want their students to learn about Black history. That raises a second problem.

What would he attack Trump on?

Sure, in a general election, there are plenty of things: Trump was a bad president and is an even worse person, every day of his administration was dominated by drama and mayhem, the way he lies and makes everything about his personal grievances is really tiresome, he is facing some serious legal troubles, he was impeached twice… oh, and then there is the small matter of the Big Lie that culminated in an attempted coup.

People tend to forget about these flaws, but once Trump puts himself front and center again — with an assist from the media because he makes them so much money — they’ll remember.

However, in a GOP primary, none of these are effective lines of attack because Republican voters (i.e., consumers of Fox News and other right-wing media) have been conditioned not to care.

To conservatives, Trump is a gift from God and, as he keeps telling them, the best president ever (according to a poll of Republican voters conducted only a few weeks after January 6).

They loved the drama and mayhem because it was Trump sticking it to the deep state and the liberal elites.

In their minds, his lies aren’t lies. And the Big Lie? They believe Trump would have won if not for all that voter fraud (for which there is no evidence).

His legal troubles are all witch hunts by Soros-backed prosecutors who are out to get him because he was such an awesome president.

Same with the impeachments.

And January 6? Sure, initially, many Republicans weren’t happy about it, but they have learned not to care. Now, most of them feel that it was either carried out by patriotic tourists engaged in legitimate political discourse — or was the work of Antifa saboteurs and FBI informants.

But, let’s assume that DeSantis does decide to go after Trump and that he does fight him as viciously as he fights ex-cons who want to vote, and that he does make inroads with some voters, there is another problem: The former president has been very effective in making his base believe that any attack on him is an attack on them.

Therefore, even if DeSantis is successful with some voters, it will likely backfire with others to the degree that hard-core Trump loyalists will resent him and never support him.

However, for argument’s sake, let’s say that DeSantis does decide to go after Trump and that he does fight him as viciously as he fights immigrants looking for a better life and that he does make inroads with some voters and that the backlash isn’t so bad, there is one final hurdle to overcome: The former president has rigged the primary process in his favor.

Not only that, but, because Trump  demands loyalty from everybody, DeSantis and any surrogate who might want to attack him on any of the above issues are likely to be on record somewhere defending the very behavior they are now criticizing.

Take the governor himself.

If, for example, Trump is indicted for crimes related to his handling of classified documents, how can DeSantis credibly attack the former president on that score after coming to his defense for just such behavior at the time?

For all of these reasons, it seems extremely unlikely that DeSantis can defeat Trump. Unless, of course, the former president ends up in jail before the primary is over.

At that point, however, the governor will face a new set of challenges: The country will have gotten to know him, he will have had to take radical positions that further alienate many voters to try to win the primary, and there is no way Trump will ever endorse a man who defeated him.

All of that being said, we think it’s great that DeSantis jumped into the race and that deep-pocketed donors are filling his campaign coffers with millions of dollars.

For the sake of America and the world, may this primary be long-lasting and as revelatory of the two participants as possible.

The cartoon above was created by DonkeyHotey for WhoWhatWhy from these images: Donald Trump caricature (DonkeyHotey / Flickr – CC BY-SA 2.0), Ron DeSantis caricature (DonkeyHotey / Flickr – CC BY-SA 2.0), books (cottonbro studio / Pexels), burning book (Екатерина Шумских / Pexels), and Mar-a-Lago (Trump White House Archived / Flickr).


  • DonkeyHotey

    DonkeyHotey creates art to illustrate news articles and opinion pieces. His current work is a combination of caricature, photo collage, and photo manipulation.

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  • Klaus Marre

    Klaus Marre is a writer, editor, former congressional reporter, and director of the WhoWhatWhy Mentor Apprentice Program. Follow him on Twitter @KlausMarre.

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