Ron DeSantis Had a Tough Summer

While summer isn’t quite over yet, it’s been a rough one for Florida Gov. Ron DeSantis.

Since his campaign announcement back in May, it’s been a treacherous slog battling Donald Trump for the 2024 Republican nomination.

As of last week, when the top GOP candidates met in Milwaukee for the first debate, DeSantis had a make-or-break opportunity to come out swinging and cement his position as the best Trump alternative.

By most accounts, he did not.

Recent DeSantis news hasn’t been good since the debate, either. For example, there’s the story about the DeSantis Super PAC desperately in need of $50 million before the next GOP debate at the end of September, according to the New York Times:

The DeSantis Super PAC issued an urgent plea to donors that the campaign needs $50 million by the end of the year, during a private meeting on August 23 in Milwaukee right before the last Republican primary debate, according to reports.

“The day after Labor Day we’re launching and we need your help to stay up and go hard the rest of the way. We need 50 million bucks,” he reportedly said.

Roe said he needed the $50 million “in the next month” before the second Republican primary debate, on September 27 — which would include $5 million per month just to sustain Iowa operations, the Times reported.

“We just need your help getting $50 million more by the end of the year, and $100 million more by the end of March,” he said. “I’m not worried about the second 50. We need the first 50.”

Roe painted the situation as dire, according to the Times’ report.

He said DeSantis needed to beat former President Donald Trump “in the next 60 days” and separate from all of his other rivals “now.”

Exactly how does DeSantis “beat” Trump in the next 60 days when he hasn’t been able to beat him in the previous 60 days? Nothing is going to change much between now and then, aside from another debate, that could alter the trajectory of the campaign.

Trump’s mugshot proved to be a boon for his coffers raising nearly $10 million in a matter of days. How is DeSantis to compete with that level of intrigue and interest from small-dollar grassroots donors?

Beyond the super PAC problems, which are more of an embarrassment than a campaign problem, DeSantis is also still looking sketchy at times on the campaign trail.

Take this example of a question from a 15-year-old high school student that DeSantis should be able to handle by now, per the Daily Beast:

It all started with a straightforward question. In June, when DeSantis stopped for a town hall event in Hollis, Mitchell raised his hand in the crowd.

“Do you believe that Trump violated the peaceful transfer of power,” the teenager asked the governor, “a key principle of American democracy that we must uphold?”

DeSantis dodged the question and said Americans shouldn’t get stuck in the past, but not before remarking—in a somewhat impressed, incredulous tone—on Mitchell’s age. “Are you in high school?” the governor asked.

The moment went viral, with DeSantis’ non-answer encapsulating how even Donald Trump’s lead primary rival could not bring himself to acknowledge the former president’s efforts to undo the 2020 election. CNN even played it during an interview with Chris Christie to tee up a question to the Trump foe.

Was DeSantis not prepared to take this question? It’s been a mainstay of journalists to trip up the candidates and force them to either defend Trump or deny him.

DeSantis could have shot back pointing out that Trump didn’t interfere with any peaceful transfer of power, Joe Biden took over and Trump left the White House like every president before him. Or, he could’ve pointed out that questioning election results or investigating fraud is not the same as questioning the free transfer of power or interfering with democracy.

There are a number of ways DeSantis could’ve handled it, but he deflected, and the questioner, 15-year-old Quinn Mitchell, followed him to more campaign events during the summer, eventually being man-handled by security:

For Mitchell, however, the exchange kicked off a series of events that deeply rattled him and his family.

Speaking about it for the first time in an interview with The Daily Beast, Mitchell says that he was grabbed and physically intimidated by DeSantis security at two subsequent campaign stops, where the candidate’s staffers also monitored him in a way he perceived as hostile.

The experience, Mitchell said, was “horrifying” and amounted to “intimidation.”

At a Fourth of July parade DeSantis attended, Mitchell was swarmed by security and physically restrained after a brief interaction with the governor—with his private security contractors even demanding Mitchell stay put until they said so.

It’s an illustration of the tightrope DeSantis is walking, and it’s not working for him. He’d be better off staking out one position but deflecting the question is akin to showing fear of angering one constituency or another, the anti-Trump or pro-Trump factions of the GOP.

All-in-all, DeSantis is in a precarious position heading into September, the typical period when more voters start paying attention. Maybe that’s good for him if he can start putting points on the board soon when more voters are tuning in.

Can he recover with a third or fourth campaign reboot? Stay tuned.