Ron DeSantis is never going to beat Donald Trump this way

Playing nice doesn't work.

(Donald Trump and Ron DeSantis)

In the wake of Donald Trump’s CNN town hall last week, Never Back Down, a super PAC aligned with Florida Gov. Ron DeSantis, tweeted out a full frontal assault on the former president.

It read¹:

On CNN tonight, Trump spent an hour talking about:

- What he did or didn't do on January 6, 2021

- Whether he will pardon people who harmed police officers - How the 2020 election was rigged

- Whether he supports terminating parts of the U.S. Constitution or the whole thing because the 2020 election was rigged

- The sex abuse case he was just found guilty in

- A cat named "Vagina"

- His defense of his comments about grabbing women by their genitals

- The federal investigation into his stash of taxpayer-owned classified documents at Mar-a-Lago

- The investigation into his efforts to reverse his 2020 loss to Biden in Georgia

How does this Make America Great Again?

It was a pretty damn effective message. And a sign — I thought — that DeSantis and his team were taking the gloves off against Trump. Finally.

Except…

A story in Semafor Tuesday morning suggests that DeSantis world thought that the tweet was a mistake — having gone too far in its negativity against Trump.

Here’s the key bit from the piece:

One DeSantis ally familiar with their thinking told Semafor that the group’s leadership “100%” recognized it as an error. A second source familiar with the situation added that they were told the tweet was sent without the approval of the PAC’s senior communications team.

“That post was a massive mistake,” the first ally said. “It sounded like it came from CNN, and I think people inside realized that that was a massive mistake, and I hope it won’t be repeated again.”

Wait, what? Have Republicans learned nothing from the last 8 years of Trump dominance?

The simple fact is that playing nice with Trump has never worked. He will not reciprocate. He will view your niceness — or, at least, willingness to pull punches — as weakness. He will sense you aren’t willing to do what needs to be done — and he will pounce.²

This is a man who said, in the course of the 2016 campaign, that a) Ted Cruz’s wife was ugly b) Ted Cruz’s father may have been involved in the assassination of John F. Kennedy and c) Ted Cruz had a birther issue and d) Hillary Clinton was hiding some sort of terminal illness from the public.

There’s a million more examples but you get the idea: Trump will say and do anything in service of winning. Literally, anything. He will not apologize. He will not second guess himself. He will just attack — and let the chips fall.

That situation is exacerbated further in the 2024 election by the fact that Trump is the clear frontrunner for the nomination. Unlike 2016, he isn’t starting in the middle of the pack. He is at the top of the heap — by a lot. The Real Clear Politics polling average puts him ahead by 34(!) points.

In order to overcome a gap like that, you need to find a way — or, ideally, ways — to peel a large number of voters away from Trump.

And it’s very hard to imagine DeSantis doing that unless he is willing to fight like hell.

The simple fact is that saying — as DeSantis is doing now — that he is everything good about Trump without any of the negatives (Trumpism without Trump) isn’t going to be enough to beat Trump.

The former president’s lead is just too big. And his followers are just too devoted to him.

Now, going negative, of course, does carry risk — for DeSantis or anyone else who does it.

Trump appears to be held to a different standard than all of his opponents by voters. He can say and do stuff that likely would be seen as unacceptable by any of the people running against him.

Witness the fact that in the last few months, Trump has been indicted on allegations of paying hush money to a porn star to cover up a relationship they had and been found liable of sexual abuse and defamation in another case.

That would end — or severely hamstring — most candidate’s campaigns. For Trump, it has managed to boost his standing in the polls.

There is then a real possibility that negative attacks on Trump boomerang back on the person making them.

But it’s a risk you have to take! Because if you don’t go after Trump, he is going to win the nomination.

Right now it seems as though every one in the race — including DeSantis, who will formally enter the contest soon — is waiting for everyone else to take the first sustained negative run at Trump.

I get the “why” there. There’s a pervasive sense that being the one to go after Trump in a real and aggressive way amounts to a sort of kamikaze mission. That you might hurt Trump but you will doom yourself.

But, history is instructive here. In the 2016 campaign, every campaign waited for the other campaigns to be the ones who crashed themselves into Trump. By the time any did — Marco Rubio and Cruz took runs at it — the race was already effectively over.

Running against Trump represents an asymmetrical — and deeply unorthodox — challenge. He is a street fighter. He will poke you in the eye. He will kick you in the groin. He will smash a chair over your head. He will do whatever it takes to win.

My sense is that to beat him, you have to be willing to match him blow for blow. You have to show him that you are also willing to do anything to win.

Backing away from negative attacks — as the DeSantis team is doing —is a mistake. The only path around Trump is through Trump. The sooner someone realizes that, the better their chances of actually beating Trump.

1. Still annoyed that Twitter is blocking tweets from being embedded in Substack. So dumb.

2. The opposite is also true. When Marco Rubio went after Trump’s hand size in 2016, Trump respected him more! “I also happen to call [Rubio] a lightweight, OK, and I have said that,
Trump said at the time. “So, I would like to take that back. He’s really not that much of a lightweight.”