For DeSantis, an Unforced Error Amplifies a Daunting Debate Challenge

MIAMI — The first Republican presidential debate next week was already looking like a stern test for Gov. Ron DeSantis of Florida, who is battling to overcome sagging national poll numbers, a fundraising crunch and an overhaul of his top campaign staff.

Now his tall task appears towering.

On Thursday, key details about how he might approach the crucial debate were revealed in a report from The New York Times about a trove of documents posted online by a political consulting firm associated with Never Back Down, the super political action committee that has in many ways taken over his campaign.

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The advice on display, which included potential attack lines and debate tactics, could be somewhat condescending — reminding DeSantis, for example, that he should be “showing emotion” when discussing his wife and children. Other parts were perhaps too revealing: suggesting that the governor attack entrepreneur Vivek Ramaswamy, who has been gaining on him in the polls but had otherwise not been widely seen as a candidate on DeSantis’ level.

The disclosure of the documents seemed to leave DeSantis in something of a no-win situation. Follow the advice too closely, and he risks walking into a political buzz saw, with his rivals painting him as overly rehearsed, inauthentic or beholden to political consultants. Ignoring it may be the likelier route — but could also leave DeSantis open to criticisms that he failed to meet expectations, for instance, by not taking down Ramaswamy.

“I don’t think anybody is going to have a harder job at the debate than Ron DeSantis,” said Alex Conant, a Republican strategist who worked on the 2016 presidential campaign of Sen. Marco Rubio, R-Fla. “He’s fighting a lot of skepticism and a lot of hungry challengers.”

As for the documents, Conant described their exposure as an unforced error: “The less you say about your strategy ahead of a debate, the better off you’re going to be.”

DeSantis’ campaign suggested late Thursday that Never Back Down’s advice had revealed nothing about his debate strategy.

“This was not a campaign memo and we were not aware of it prior to the article,” Andrew Romeo, the campaign’s communications director, said in a statement. “We are well accustomed to the attacks from all sides as the media and other candidates realize Ron DeSantis is the strongest candidate best positioned to take down Joe Biden.”

Onstage Wednesday, those attacks, and DeSantis’ response to them, could be the gravest risk: He has appeared prickly in past debates and had gaffes exploited by his opponents. Current rivals like former Gov. Chris Christie of New Jersey, a notoriously pugnacious debater, could pose a threat.

So could other challengers seeking to dethrone DeSantis as the race’s No. 2, including Sen. Tim Scott, R-S.C.; the smooth-talking Ramaswamy; or even former Vice President Mike Pence, a longtime conservative talk radio host accustomed to verbal sparring.

DeSantis’ allies still hope that the governor will use the debate in Milwaukee to break out from the wide field of contenders who have prevented him from coalescing broader support. The debate, they say, is the first time that many Americans will tune in to the 2024 campaign, allowing DeSantis to tell his story to the largest audience he has ever faced.

DeSantis has been preparing for the debate with practice sessions at least once a week. He is expected to highlight his policy proposals on immigration, the economy and countering China. He has also been doing a steady round of interviews with mainstream news outlets, where he has faced tougher questions.

Much has depended on whether former President Donald Trump, the spotlight-grabbing showman, shows up. On Friday, The New York Times reported that Trump had told people close to him that he had made up his mind to skip the debate. Instead, he is said to be planning to hold an online interview with former Fox News host Tucker Carlson.

Regardless of Trump’s attendance at the debate, taking him on remains a problem.

The documents from Never Back Down advise DeSantis to defend Trump when Christie, a Trump critic, attacks him but to tell voters that he is the candidate “who will keep the movement that Donald Trump started going.”

DeSantis has walked a similarly fine line in his criticisms of Trump this summer, chiding him for not debating and failing to “drain the swamp” as president. But he has also been careful not to offend the former president’s legion of supporters.

Without Trump onstage, DeSantis will be the de facto front-runner, meaning he could face a barrage of attacks.

Wearing the bull’s-eye could prove uncomfortable for DeSantis, a 44-year-old Harvard-trained lawyer known to bristle under criticism. His opponents will hope to score viral moments highlighting his defensiveness and casting him as awkward and robotic. A meme-able gaffe, no matter how transitory, runs the risk of overshadowing any strength he might project as a policy expert or a decisive young leader.

DeSantis’ most prominent debates — in his contests for governor against Charlie Crist, a former Republican governor of Florida turned Democratic member of Congress, and Andrew Gillum, at the time the mayor of Tallahassee, Florida — do not necessarily offer hope to his supporters. They are now largely remembered for encounters that left DeSantis angry or tongue-tied.

Last year, as DeSantis ran for reelection with his sights already set on the presidential race, Crist asked his rival if he would “look in the eyes of the people of the state of Florida” and pledge to serve a full term.

“Yes or no?” Crist said, turning to DeSantis, who stood silent and stone-faced, refusing to answer.

“Yes or no, Ron?” Crist asked again, taking advantage of the dead air.

(By the debate rules, candidates were not allowed to question each other directly — a prohibition Crist ignored.)

Finally, DeSantis spoke. “Is it my time?” he asked the moderator.

“It’s a fair question,” Crist continued. Then he turned to the audience. “He won’t tell you.”

By the time DeSantis broke the awkwardness to deliver a seemingly rehearsed counterpunch, calling Crist a “worn-out old donkey,” the damage had been done.

It was exactly the kind of moment the Crist campaign had been gunning for.

“DeSantis doesn’t take punches well,” said Joshua Karp, a Democratic strategist who led Crist’s debate preparations. “And his fundamental problem as a communicator is that he’s either attacking or explaining. He’s never telling a story. He’s never reaching people from the heart.”

Karp, who also led Gillum’s debate preparations four years earlier, said DeSantis struggled with a challenging aspect of debating: “Listening to what your opponent has to say and then deploying the right amount of warmth and strength and dexterity to counter it.”

That weakness was on display against Gillum in 2018.

At the time, DeSantis was under fire for having said that voters should not “monkey this up” by electing Gillum, who is Black. His comments were widely criticized as racist.

Confronted by the debate moderator, DeSantis angrily interrupted, his voice rising as he said he had stood up for people of all races as a military lawyer and prosecutor. “I am not going to bow down to the altar of political correctness,” he added. “I am not going to let the media smear me.”

Gillum, known as a gifted public speaker, seized on the opportunity.

“My grandmother used to say, ‘A hit dog will holler,’ and it hollered through this room,” he said of DeSantis, before landing a strong blow: “Now, I’m not calling Mr. DeSantis a racist. I’m simply saying the racists believe he’s a racist.”

DeSantis visibly winced and scoffed.

He had prepared for the confrontation, according to tapes of his debate practice sessions that were leaked this year and first reported by ABC News. One of his advisers, Rep. Byron Donalds, R-Fla., a DeSantis ally who has since endorsed Trump, had urged him to express regret to those who had been offended. (Donalds is Black.)

But DeSantis insisted on an aggressive response.

“If I show any weakness on that, I think I lose my base. I think that I appear to be less than a leader,” he said. “And so, I just think I’ve got to come at it full throttle and say that’s wrong.”

Separately, in an echo of the advice offered by Never Back Down, the tapes show an adviser telling DeSantis that he should write the word “likable” in capital letters at the top of his notebook as a reminder.

Despite the debate stumbles, DeSantis won both elections, squeaking past Gillum and then crushing Crist four years later. And his showing in the 2018 Republican primary debates, when he was able to cast himself as a Trump-backed insurgent, received better reviews.

Next week, Trump’s campaign will be paying close attention to the most minute aspects of DeSantis’ performance.

“There will be an entire war room team that will be watching and highlighting each awkward thing DeSantis does,” said Steven Cheung, a spokesperson for the Trump campaign. “He needs to be on his best behavior.”

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