DeSantis hits Trump below the belt. Will this new strategy work?

For months, Republican presidential candidate Gov. Ron DeSantis (R-FL) has been more willing to attack former President Donald Trump in their escalating 2024 primary race. But this week marked a new level of just how far the Florida governor’s campaign is willing to go in his battle against Trump and the rest of the GOP presidential field.

DeSantis has begun taunting Trump over skipping the Republican National Committee-sponsored primary debates in response to Trump’s recent provocations. “If Donald Trump can summon the balls to show up to the debate, I’ll wear a boot on my head,” DeSantis told Newsmax in an interview this week. His campaign is also selling golf balls that say, “Ron DeSantis has a pair. He shows up.”

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The former president, in turn, has mocked DeSantis, his closest 2024 competitor, over allegations the cowboy boots the governor frequently wears while campaigning have hidden heels that boost his height. But DeSantis’s willingness to hit back at Trump with references to his manhood marks a newer and riskier strategy for DeSantis ahead of next week’s debate in Miami, Florida, and the Iowa caucuses in January.

The Trump campaign, in the meantime, is undeterred by DeSantis’s mockery. “DeSantis’s campaign is now mired in the mud and spending their entire day responding to what we’re doing. They fell right into the trap,” Steven Cheung, Trump’s spokesman, told the Washington Examiner. “Meanwhile, the Trump campaign is releasing new Agenda47 policy proposals and making the case against Crooked Joe Biden. DeSantis’s offering to wear a boot on his head just shows how desperate and pathetic he is. He might as well wear a dog collar with a leash and run alongside golf carts.”

The DeSantis campaign claims the governor is the only Republican candidate who can defeat President Joe Biden, often pointing to Trump’s baggage as a distraction from the 2024 race. DeSantis has made winning the Iowa caucuses the crux of his campaign and pledged to visit all 99 counties in the state, while Trump has noticeably increased the number of campaign stops in the Hawkeye State.

“Ron DeSantis has Donald Trump on defense, and the former president knows it, which is why this week alone, his team is spending nearly $1 million on negative ads attacking DeSantis in Iowa despite previously beating their chest about shifting strategy to focus on the general election and Joe Biden,” said Carly Atchison, DeSantis’s national campaign spokeswoman. “DeSantis is the only candidate who can beat both Trump and Biden and lead America’s comeback.”

Republican experts told the Washington Examiner that it is only inevitable that DeSantis would resort to even harsher excoriations of Trump due to his unceasing dominance in the primary and de facto incumbency status. “There’s this kind of principle that in campaigns, if you’re going to take down the incumbent, you have to go negative. And obviously, Trump’s not the incumbent now, but in the Republican Party sense, he sort of is,” said Steve Hilding, a Republican strategist and vice president of political consulting firm McShane.

Similarly, Christopher Nicholas, a veteran Republican political consultant, claimed: “Months ago, just a few of the other GOP candidates dared to publicly attack the former president. Now, it’s the rare one who doesn’t.”

Hilding pointed to Trump’s ability to overcome an onslaught in ways that other more traditional candidates would have floundered as one reason DeSantis is moving into a more down-in-the-mud fight with Trump. Win It Back PAC, an anti-Trump political action committee linked to Club for Growth, attempted to launch attack ads against Trump and his legal drama only to realize the ads increased Trump’s support, a sign of his continuing hold over the GOP base.

“At this point, though, obviously, it looks every day more and more likely that Trump is going to be the nominee. And I think that the DeSantis campaign kind of realizes that they have to kind of play on Trump’s playing field,” Hilding added. “Even before he ran for president, the kind of Twitter comments that Trump had said, and obviously anytime Trump felt there was an opponent in a political sense, he kind of got down and dirty with them. And I think that the DeSantis campaign are kind of seeing that as the only way to kind of go negative on Trump.”

DeSantis is feeling the pressure to improve his campaign with less than 73 days until the Iowa caucuses, according to another Republican strategist. “Two strategic objectives are probably driving the DeSantis decision to step up attacks against President Donald Trump. First, the election calendar is shortening. The time for movement is now,” said Matt Dole, a Republican political consultant based in Ohio. “And the way to get movement is to broadcast contrast messaging. Whether or not it will be successful is another question, but it’s the best chance for movement.”

There is some evidence that this strategy may not work. Then-presidential candidate Sen. Marco Rubio (R-FL) claimed Trump had “small hands” and implied that suggested things about the size of other aspects of his anatomy. Trump had often derogatory referred to him as “Little Marco” during the primary. Rubio would ultimately drop out of the race roughly two weeks after he made the “small hands” comment, and Trump would go on to win the nomination and the presidency.

Dole also claimed that the second factor DeSantis is facing comes from the anti-Trump faction of the GOP who want one candidate they can support against the former president.

“Remember, part of why they support DeSantis is because they don’t support Trump and they want to see a candidate who’s their mouthpiece for that,” Dole said. “Furthermore, as other Republicans leave the race, DeSantis is hoping that they will come into his camp so that he can solidify himself as the natural alternative — the contrast messaging, in theory, reminds those Republicans why they’re seeking an alternative in the first place.”

So far, the lower-tiered candidates who have dropped out have either endorsed Trump, former United Nations Ambassador Nikki Haley, or, in former Vice President Mike Pence’s case, not endorsed anyone yet. But there isn’t much time left for DeSantis or any candidate to coalesce as the top candidate.

DeSantis aides, some of whom were former Trump aides, have become more willing to get into vulgar fights with Trump’s surrogates on social media, helping give the governor some cover. “There’s a level of cover that’s different. Rubio came out and just said it himself. He said it on a stage,” Hilding said. “Versus DeSantis when he’s on the stump in Iowa, he’s not saying these kinds of things. It’s coming out from the campaign on social media and from campaign surrogates on social media, campaign emails, and things like that.”

Cheung, Trump’s spokesman, mocked the DeSantis campaign for selling the golf balls on social media, prompting pushback. “Ron DeSantis is so broke he needs to sell his balls to strangers in order make rent and keep the lights on,” Cheung said.

Atchison, DeSantis’s spokeswoman, quipped back: “Your boss is in need of some because he won’t show up to debate DeSantis, so we’d thought we’d help out!”

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The GOP experts, however, cautioned that his harsher strategy may or may not work given Trump’s savvy game plan in his third presidential campaign.

“Perhaps this is a strategy that could work for DeSantis. I think it’s way too early to be seen,” Hilding concluded. “And I think that though the primary is getting closer and closer and closer and closer, I think there’s still quite a length of time to see how effective this is going to be.”