When will Ron DeSantis call Trump a loser?

To this point in the early days of the Republican primary, all the major potshots have been coming from just one candidate, directed at just one other: Donald Trump taking aim repeatedly at Ron DeSantis. Much of the media conversation about this has focused on DeSantis’s unwillingness to respond to any of these attacks: a deliberate choice that hasn’t lowered the temperature or frequency of Trump’s barbs, which now include comparing the Florida conservative to, gasp, Mitt Romney. But consider the possibility that at this moment, both men are making a political mistake.

For DeSantis, the risks of non-response are that Trump defines him before he defines himself. Republican primary voters generally know who Ron DeSantis is and have an overwhelmingly positive view of him. But he’s still limited in that definition as a Covid stalwart and culture warrior, someone who has yet to truly introduce himself to the nation and tell the story about who he is and what he could bring to the presidency. That’s presumably waiting until his announcement, which likely won’t happen before his state’s legislative session ends in May. 

The interim leaves plenty of time for Trump to define him in uncomfortable terms. There are shades of Rudy Giuliani 2008 in this — a candidate with high polling numbers saying “just wait until we really get going,” only realizing too late how quickly those numbers can soften. Glory fades, especially electoral glory — and the power of being able to say that you won bigly in Florida when your opponent was tied directly to three losing cycles in a row will fade as well. 

For Trump, the risks are more plentiful. First, his solo targeting of DeSantis clearly shows that the governor is the only potential candidate Trump truly fears — sending a signal to donors and to conservatives who want to move on from the former president that he is their best bet for success. It helps coalesce his opposition instead of keeping it diffuse, which ought to be an early priority for the campaign.

There’s also the risk, especially in the “workshopping” period of the Trump insult comedy machine, that a series of jokes, insults and opposition attacks that don’t perceptibly bring DeSantis down from his solid second position in the polls could be a sign that Trump has lost his fastball. The trouble with being a candidate who thrives on entertainment is what you do when you’re not giving audiences what they want. And since Trump’s approach has been an aggressive series of insults and allegations of globalism, fraudulence and stupidity — when he could have instead approached DeSantis as a Rubio type, patting him on the head as young and immature — it’s more telling when those punches don’t land.

Clearly DeSantis and his team think that letting Trump wear himself out this way is the best approach to trading blows in the early stages. But you can only do that for so long — so how long does he plan to keep this up? The Florida governor did offer comment on the Mar-a-Lago raid and Trump’s potential arrest. But those are bigger stories tangentially related to his state: they’re political, not personal, unlike the Donald’s broadsides.

Does DeSantis intend to avoid any pushback against Trump until the first debate in August? That seems like a clear mistake. Getting pushed around by a bully for months is no way to introduce yourself as the new alpha commander-in-chief candidate. At some point, DeSantis will have to hit back — and he’ll need to be sure to land the right blow when he does. Calling Trump a loser is pretty much the worst thing you can say to him — but it may be what someone has to do in the lead-up to 2024 to beat him.