‘The DeSantis people are rookies’: Even Trump critics say he’s running circles around DeSantis

By comparison, he said, “the DeSantis people are rookies.”

Trump’s onslaught has been disorienting for the nascent DeSantis operation. The Florida governor, who’s expected to announce his candidacy in the coming weeks, plans to make the case that he will counter Trump’s circus with a sense of normalcy that positions him to do what many Republicans fear Trump cannot: Defeat President Joe Biden. But that argument is running head first into the tidy — and muscular — organization the former president is putting together.

In recent weeks, Trump’s team has worked to bank wins before DeSantis officially enters the race. They have rolled out policy videos focused on a second Trump term and made hires in early voting states. They have developed relationships with state party leaders, met with lawmakers at Mar-a-lago and worked the phones to steal endorsements from DeSantis in his home state. Trump is even doing a town hall event with CNN, a former cable news foe of the ex-president, in an effort to reach more mainstream audiences. Now DeSantis — a politician who places a high premium on control – will be forced to catch up.

“This is a campaign run by adults who have excelled at the ‘crib kill’ strategy,” said Michael Caputo, a friend and longtime adviser to Trump, on how the campaign is targeting DeSantis by nailing down endorsements before DeSantis gets into the race. “Trump hasn’t done it before. He absolutely eschewed the congressional endorsements in 2016 and his campaign turned their nose up at it. It’s a completely different world.”

The change in that dynamic, people close to the campaign say, is due in part to Trump’s own knowledge of how the presidential campaign process works. This is, after all, his third time running. But it is also the product of a team of advisers who have had worked with Trump or on Trump-adjacent operations for years, including Susie Wiles and Chris LaCivita, as well as Brian Jack, who served as Trump’s political director in the White House.

Those advisers and others on his team have kept a low profile as they have worked behind the scenes to build out support in Congress, plan state visits and political events, put county-level operations in place, and tend to state party leaders who go on to become influential delegates. State-level GOP officials from places like Nevada and Louisiana have made visits to Mar-a-lago for fundraisers and other events, where Trump has made time to talk to them and follow through with any personal requests they have, like signing hats to auction off at home.

The dueling politicians’ strategies were described in interviews with over a dozen Republicans working for Trump, DeSantis, or in 2024 presidential politics.

Their focus on early blocking and tackling paid off when a majority of the Florida congressional delegation announced Trump endorsements just as DeSantis was visiting Washington, D.C. last month. Lawmakers said Trump had personally called and reached out. Some had only heard from a pollster for DeSantis, or revealed they had no relationship with their own state governor at all.

“The challenge that DeSantis and others face is that Donald Trump has a several years head start on this, they’ve continued to foster a significant organization across states that will make it difficult for later entrants who haven’t built that same infrastructure,” said a Republican strategist who has been in contact with almost every Republican presidential campaign. DeSantis, he said, “has a ton of money and not much organization.”

But, he added, it’s too soon for DeSantis supporters to panic. While some donors are beginning to worry that the Florida governor can’t beat Trump, those in his tightly-controlled orbit are expressing a mix of confidence in his standing as the lead alternative to Trump and hope that the ex-president’s legal troubles and recent election losses puncture his early dominance.

“Coming off of an historical re-election victory, DeSantis has the most robust political apparatus with national reach that no one is aware of,” said one person with close ties to the Florida governor, who was granted anonymity to speak freely before the campaign launches. “If he decides to run, there is no ramp up. The machine is built, full of rocket fuel and ready to launch.”

That machine begins with a deep budget, huge fundraising potential and a team of loyalists hiring staff in critical nominating states.

Never Back Down, a super PAC formed by ex-Trump staffer Ken Cuccinelli, has raised $33 million so far to support DeSantis’ pending campaign, according to a representative for the group, who was granted anonymity to speak about the fundraising ahead of an official filing in July. In addition, the $85 million war chest DeSantis built up during his gubernatorial campaign can likely be transferred into a PAC supporting his presidential bid — giving him an enormous financial advantage heading into the election.

“The energy our team is seeing for Ron DeSantis from Iowa to South Carolina day in and day out continues to build, and we are leveraging all the tools at our disposal to expand this momentum and, ultimately, get Ron DeSantis elected to the White House,” PAC spokesperson Erin Perrine said in a prepared statement.

After Trump announced a slate of congressional endorsements from DeSantis’ home state of Florida, Never Back Down rolled out the backing of 19 state lawmakers from Michigan.

“This is spring ball right now. The campaign will kick off shortly and then people will start putting points on the board,” said one Florida-based political operative who supports DeSantis but would only speak on the condition of anonymity since he is not yet an announced candidate.

The PAC, which has reportedly received $20 million from real estate mogul Robert Bigelow, has been running ads in four early voting states touting DeSantis’ blue-collar roots and conservative record.

The entity has hired operatives in Iowa, South Carolina, New Hampshire and Nevada and is staffing up its Atlanta-based senior team, including former Nevada Attorney General Adam Laxalt. It also recently launched “Students for DeSantis,” which mobilizes college students to phonebank and canvas for the campaign.

Election law prohibits coordination between PACs and campaigns, but Never Back Down has thus far been serving as the vehicle to promote DeSantis ahead of his launch.

“They’re going to use the super PAC as the ground game operation,” said someone else close to the DeSantis team, who was granted anonymity to speak openly about strategy. “The campaign is going to be basically in charge of TV messaging, the candidate’s scheduling and time. Paid media is going to be the campaign and grassroots operation is going to be the Super PAC.”

Meanwhile the governor — who returned this week from an overseas trip intended to bolster his foreign policy chops — is planning to host a dinner at his official residence in Tallahassee next week with fundraisers, according to two people familiar with the event.

Nevertheless, one political strategist working on Trump’s re-election effort said they have an inherent advantage in not having to spend millions simply introducing the public to the ex-president.

“Donald Trump is Donald Trump. We don’t have to spend a single dollar telling people why you should vote for him,” said the strategist, who was granted anonymity to discuss this stage of the race freely. “All we need to do is beat the shit out of DeSantis. So their money has to do a whole lot of different things: their super PAC has to build a ground game, tell who he is, and tell people why they shouldn’t vote for Trump.”

The pro-Trump Make America Great Again super PAC has spent millions over the past five weeks on advertising that targets DeSantis’ record on Social Security and Medicare.

Meanwhile the Trump campaign has worked on staffing in early primary states like New Hampshire. Trump’s campaign was the first to announce any hires in New Hampshire in late January when it brought on the former New Hampshire GOP chair Stephen Stepanek as a senior adviser focused on the state. In late March Trump brought on Trevor Naglieri, an alum of Jeb Bush and Ted Cruz’s presidential campaigns, as state director.

Last week in Iowa, Trump announced the endorsements of 13 state legislators and former elected officials from eastern Iowa. A Trump adviser credited some of those endorsements to the work of Trump’s hires in the state, which includes Bobby Kaufmann, the son of the Iowa GOP chairman Jeff Kaufmann, Alex Latcham, who worked in the Trump White House, and state director Marshall Moreau.

Trump’s campaign is also working on identifying potential donors or volunteers in states based on data they’ve compiled from events or from the previous two campaigns in the state. According to another Trump adviser, they have already identified 192,000 people in New Hampshire who have donated or signed up online to say they want to do something with the campaign, or attended rallies over the last six years.

That’s not to say Trump won’t inject chaos into everything again. He has been discussing the possibility of not participating in upcoming Republican primary debates. But the overall operation’s discipline is now playing out in the polls. A CBS News/YouGov Poll released on Monday showed Trump with 58 percent of support from Republican primary voters, compared to DeSantis with 22 percent.

“Definitely in the last couple of weeks there’s been a growing resignation to the likelihood that Trump may yet end up as the nominee again,” Cullen said.

Lisa Kashinsky contributed to this report.