Look him in the eye.
Get him to start whining.
Don’t assume he’s that prepared.
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Watch out for his canned lines.
But most of all, keep looking him in the eye, especially after attacking him. He doesn’t like prolonged eye contact.
These are but a few of the tips—offered by a longtime Democratic operative—for the seven Republican presidential hopefuls who will find themselves on a debate stage Wednesday night with Florida Gov. Ron DeSantis.
For two elections in a row, Joshua Karp steeped himself in DeSantis debate prep as an adviser to Andrew Gillum and Charlie Crist, the Democrats who ran and lost against DeSantis in 2018 and 2022, respectively.
More than perhaps any Republican on the debate stage in Milwaukee, Karp has an intimate knowledge of DeSantis’ strengths and weaknesses as a debater.
The Democratic operative told The Daily Beast he’s spent countless hours “watching film” on DeSantis, as if he were a college football scout fixated on a blue chip recruit.
But what surprised Karp the most after extensively preparing two very different Democratic candidates for debates against DeSantis was the lack of polish from the Republican, who otherwise came across smoothly on TV in the right setting.
“Basically from the jump, it was clear he hadn’t prepared at all,” Karp said.
It seems unlikely the same will be the case for DeSantis ahead of the first GOP presidential debate, which is crucial for his 2024 aspirations. The event is the Florida governor’s best chance yet to kickstart his stalling campaign, currently on its third reboot in not quite as many months.
Former President Donald Trump’s decision to skip the debate also gives DeSantis—who will be standing in center stage—the opportunity to manifest a vision of the GOP he is trying to forge into reality, said Karp.
“A win for DeSantis is coming out of the debate looking like the frontrunner on a stage that doesn’t have Donald Trump,” Karp said. “Like, give the Republican Party a picture of a party that doesn’t have Donald Trump in it.”
But the governor’s 2024 bid has been dogged by scrutiny and punditry spotlighting his awkwardness on the campaign trail and his apparent discomfort in unscripted interviews and interactions.
For the other GOP presidential hopefuls on stage, DeSantis—and his diminished yet still substantial share of the primary electorate—is ripe for the taking. Even the governor’s allies have admitted he will likely bear the brunt of the attacks flying across the stage on Wednesday night.
For candidates willing to go the extra mile and set a trap for DeSantis based on his past behavior, the spoils of a campaign-defining moment at the expense of the field’s clear number two could be all theirs.
“Ron DeSantis has never learned how to take a punch,” Karp said. “He can’t counterpunch with more force. The big test of this debate is whether he is able to control those bad instincts that he's got.”
The DeSantis campaign did not respond to a request for comment for this story.
Karp had a front row seat to the early DeSantis debate moments his GOP rivals may be closely reviewing now. Yes, his candidates ultimately lost to DeSantis both times, Gillum by just 0.4 percent of the vote in 2018, and Crist by more than 19 points in a 2022 blowout.
But Karp remains adamant those signs of DeSantis’ future struggles were obvious all along in his gubernatorial debates.
Perhaps the most glaring example was DeSantis’ deer-in-the-headlights moment against Crist in 2022. In their only debate, the governor was caught completely off guard by his Democratic opponent, whom Karp described as “not naturally a good or poor debater, but a hard worker.”
Having watched his film, Crist knew where and how to strike: at DeSantis’ obvious presidential ambitions.
“Why don’t you look in the eyes of the people of the state of Florida and say to them, if you’re re-elected, you will serve a full four-year term as governor?” Crist asked, while keeping his gaze focused on DeSantis, who stayed frozen. “Yes or no?”
Staring ahead intently, DeSantis remained silent for a very long 10 seconds. His eyes began to twitch before he glanced at the moderator and referenced the rule that he did not have to answer questions from his opponent.
When the awkwardness subsided, DeSantis eventually got back to his more polished attack line on Crist, which neatly doubled as a jab at President Joe Biden. “The only worn-out old donkey I’m looking to put out to pasture,” he said, “is Charlie Crist.”
The semi-viral moment marked perhaps the high point of any optimism behind Crist, a former Republican governor who always faced long odds to topple DeSantis.
But things were different in 2018, when DeSantis was a relatively unknown quantity who was locked in a toss-up race against Gillum, then the popular mayor of Tallahassee. (He has since been indicted on corruption charges; they were dropped in May after a mistrial.)
Then, Karp looked at DeSantis’ resume as a Navy JAG officer with a pair of Ivy League degrees—not to mention his competitive streak, which eventually led him to four varsity letters at Yale—as indicators he would put up a strong fight.
Instead, they got the DeSantis the rest of the GOP has become more acquainted with since launching his 2024 campaign in late May.
Karp predicted DeSantis would come at Gillum hard on culture war issues such as defunding the police, a contentious issue at the time. But DeSantis kept picking fights with the moderators and appeared not to know the rules of the debate format.
“What we didn't predict was how whiny, argumentative, and ineffective he would be at that,” he said.
Then DeSantis laid a trap for himself and gave Gillum his viral moment.
After cutting off the moderator’s question about appearing at four events hosted by a white supremacist who used racial slurs to refer to former President Barack Obama and called him a “Muslim,” DeSantis’ voice cracked as he avoided condemning the rhetoric. “How the hell am I supposed to know every single statement somebody makes?” he asked.
Gillum had a knockout blow ready to go.
“My grandmother used to say a hit dog will holler,” Gillum said. “And it hollered through this room… Now, I’m not calling Mr. DeSantis a racist, I’m simply saying the racists believe he’s a racist.”
“Everyone credits Andrew Gillum with amazing delivery of those lines,” Karp said. “Andrew Gillum is an amazing debater, but it’s DeSantis who set himself up for that.”
In the GOP primary, for a skilled debater like former Gov. Chris Christie, DeSantis may prove to be an ideal target the second he gets flustered, Karp said.
“I think the biggest threat to Ron DeSantis on the debate stage is Ron DeSantis, but right over his shoulder is Chris Christie,” he argued.
Christie comes into the debate with some of the hottest anticipation around his performance, leaving a high bar after exiting the 2016 race with an evisceration of Sen. Marco Rubio (R-FL), who inadvertently kept repeating a line about Obama.
Then there’s the brewing feud between DeSantis and entrepreneur Vivek Ramaswamy, who, as The Daily Beast reported last week, has decided to mostly skip conventional debate prep, save for a few foreign policy briefings and a three-hour topless tennis session.
Ramaswamy has slowly climbed in the polls and is close to surpassing DeSantis nationally. The pro-DeSantis PAC Never Back Down took notice: In a lengthy debate memo reported by The New York Times, the PAC telegraphed to DeSantis a strategy of taking “a sledgehammer” to Ramaswamy.
For the non-Christie candidates, Karp said the best way to get under DeSantis’ skin is to keep it simple.
“It depends on the chemistry in the room, but one of the things that Charlie did that was particularly effective was he made eye contact with the camera and the viewers back home, and when Desantis was attacking him, he looked at DeSantis,” the Democrat said.
Still, there’s a silver lining for DeSantis, even in the eyes of a hardened opponent who’s watched him like a hawk.
“The bar for Ron DeSantis is in the basement right now. Everyone knows this is not a format in which he excels,” Karp said. “So it wouldn’t surprise me if a lot of commentators view him as doing well in the debate just because expectations are so low.”
But the brutal 2024 GOP presidential primary is hardly a breezy 2022 Florida re-election campaign, where a bad viral moment was a mere speed bump for DeSantis on the way to a landslide victory. With the world watching the stage in Milwaukee, even a minor misstep could cement the governor’s reputation.
“What his opponents need to do is trigger the same responses that Andrew Gillum and Charlie Crist were able to,” Karp said. “The whiny, off-putting, bratty demeanor that comes off whenever he’s challenged.”
