Trump prepares an extensive opposition file on ‘Ron DeSanctimonious’

Florida Gov. Ron DeSantis has not yet officially entered the 2024 presidential arena but former President Donald Trump’s campaign is preparing a grenade to launch his way.

Trump’s team and his allied PAC are preparing an expansive opposition research file by poring over DeSantis’ record as a prosecutor, member of Congress, and Florida governor. Among the items a Trump-allied group has drilled into is DeSantis’ record while serving as an assistant U.S. Attorney before running for congressional office, with plans to accuse him of being an “extremely lenient prosecutor” in cases involving, among other things, child pornography.

They have recently conducted focus groups and looked at polling to hone in on the best messaging to take on DeSantis. And they’re wasting no time to get organized and scoop up talent in key primary states.

“The team itself has felt like he has had a free ride without scrutiny for a number of years,” said Bryan Lanza, who worked on Trump’s 2016 campaign and remains close to Trump’s team. “Just because he’s aggressive and willing to fight doesn’t make him MAGA. MAGA is the policies and there is a tremendous amount of sunlight between Trump policies and DeSantis policies. The more and more that gets highlighted the more DeSantis is going to get exposed as just another member of the establishment and compared to Jeb Bush.”

The preparations are the latest sign of a bruising primary fight to come, one that could make the 2016 primary fireworks look tame in comparison. It’s a high-risk, high-reward play. The child pornography charges, for one, mirror those used by Republican Senators against then Supreme Court Justice nominee Ketanji Brown Jackson. And in the case of DeSantis, his contemporaries have insisted that the plea deals he signed were not unordinary.

“To make any allegation that he was soft on any kind of case, especially child pornography, is just ludicrous. It defies the logic of what I saw in the office or what my office would let happen,” Ronald Henry, a retired assistant U.S. Attorney who served as supervisor to DeSantis when he was special assistant U.S. Attorney, told POLITICO. “He wasn’t a lone wolf on his own making deals without the entire weight of the U.S. Attorney’s office overseeing what he was doing.”

Already, Trump has seen several notable defections from his camp, with former allies citing the ex-president’s “childish” antics.

“Trump was a good policy guy and I’d put him up there with Ronald Reagan on policy, but presidentially he was a disaster the way he acted, the calling people names,” said former congressman Tom Marino, who co-chaired Trump’s 2015 campaign in Pennsylvania but is now supporting DeSantis. “He’s just not a nice person…If he thinks he had trouble getting elected before, there are more and more people out there across the country who said I was for him the first time, the second time, but what’s going on and his problems I don’t think I can support him.”

Trump hasn’t waited to get started on what is expected to be a major anti-DeSantis broadside. He’s made digs at the Florida governor’s backpedaling on raising the retirement age and privatizing Social Security and Medicare, has floated unsavory questions about DeSantis’ time as a teacher in Georgia, and has considered different nicknames for the governor including “Ron Establishment” and “Tiny D,” which he told reporters he likes. For now he is settling on “Ron DeSanctimonious,” or, for short, “DeSanctus.” Trump denied he was ever considering another oft-mentioned nickname — “Meatball Ron” — and told reporters it is “too crude.”

“I’m a very loyal person,” Trump told a small group of reporters on his way to Iowa on Monday. “There’s no hostility but I think it’s a strange thing he was out of politics, he was dead…I don’t think it’s nasty. I’m a very loyal person so I don’t understand disloyalty but you do see it in politics.”

Trump even released a video on Tuesday praising past Florida governors and claiming the state was “doing fantastically” before DeSantis. “Sunshine and ocean are very alluring, it’s not too hard to work with those factors.”

The Trump campaign’s goal is to capitalize on the months before DeSantis announces by rolling out new attacklines on the Florida governor and painting him as the handpicked establishment favorite, not the heir apparent to the MAGA throne.

DeSantis himself has brushed off Trump’s attacks as mere noise.

A spokesperson for DeSantis declined to comment.

“DeSantis doesn’t need to promote himself,” Marino said. “He’s a leader. He doesn’t call people names. He doesn’t make fun of women. That’s an easy one. I truly meant Trump was a genius on policy and he really blew it. I told him about it. He knows it all.”

In public remarks, DeSantis has drawn a contrast with Trump without naming him by emphasizing his overwhelming win in 2022, noting that he doesn’t rely on polls — a favorite tool of Trump’s — to dictate decisions, and that his administration is leak free.

But the rivalry that has been simmering for months could start to boil over as the two men criss-cross the country, hob nob with donors in the wealthy enclaves of Palm Beach, and start to unveil key campaign support.

On Friday, DeSantis made two stops in Iowa as part of a tour for his book, “The Courage to be Free,” and visited Nevada on Saturday. Trump visited Iowa on Monday for a roundtable on education policy.

As DeSantis spoke to Iowans, Trump went after the Florida governor on Truth Social, taking aim at his “very small crowds,” his support for ending an ethanol mandate, and his votes on Social Security and Medicare.

DeSantis did not mention 2024 during his speech in Iowa, but his decision to visit the state that holds the first contest in the Republican nominating calendar indicated he is doing more than flirting with a run. DeSantis is not expected to make a presidential announcement until Florida’s legislative session ends in May.

DeSantis’ Iowa visit came as a new aligned group, Never Back Down PAC, launched on Thursday. That group is being led by Ken Cuccinelli, one of Trump’s former administration officials. And in a potential sign of defections to come, Marino and another former Trump booster, Lou Barletta from Pennsylvania, also announced they plan to support the committee.

Some Trump allies acknowledge DeSantis has been able to attract deep-pocketed donors and some establishment Republicans who are eager to move on from the constant chaos of Trump. They say it could be challenging for him to bring together that cohort and some of the populist, right-wing voters who have been a part of the ex-president’s base in the past.

Trump’s team has tried to drive a wedge between the two by highlighting DeSantis’ voting record in Congress on support for military involvement overseas and entitlement cuts. They’re also keen to go after DeSantis’ response to Covid, although it is unclear how potent of an attack line that will be to voters who saw thousands flock to the Sunshine State during the pandemic.

But they also plan to highlight what’s described as the “personality factor.” Trump allies say the Florida governor can be awkward and mechanical in public, and note he has largely avoided the press. To contrast that, Trump’s team organized a trip to East Palestine, Ohio to bring attention to the train derailment there and interact with residents affected by the crash. They have given local and national media opportunities to ask Trump questions, and have scheduled unannounced stops in places like McDonald’s where he can interact with the public.

Trump’s team also sees an inherent advantage within their ranks. The top lieutenants for Trump’s campaign and aligned PAC, including Susie Wiles, Jason Miller, Taylor Budowich, Justin Caporale, and Tony Fabrizio, all of whom have past experience working for DeSantis.

One of Trump’s aides noted that it was a reflection of DeSantis’ high staff turnover, although Trump himself has cycled through dozens of top aides over the years, often in very messy and public ways — a fact DeSantis has referenced. Indeed, some of Trump’s top administration officials like Haley, Pence, and Pompeo, have announced a presidential run or are actively considering it.

“You look at my administration, part of the reason we’re able to do well, they’re not leaking to the media, we don’t have palace intrigue, we don’t have any drama. It’s just execution every single day, and we end up beating the left every single day for four years,” DeSantis said in Des Moines.

When asked by POLITICO at the recent CPAC gathering what that might say about his own leadership, Trump described his former cabinet officials as “ambitious” and said he was “proud” of their accomplishments working under him. “The more the merrier,” he added of them entering the campaign.

Alex Isenstadt contributed to this report from Davenport, Iowa.