Florida Governor Ron DeSantis speaks during a book tour visit at Adventure Outdoors gun shop in Smyrna, Georgia, on March 30.
CNN  — 

For much of the past two years, Florida Gov. Ron DeSantis has shaped his political narrative with rapid-fire policy moves and a resounding reelection victory fueling his ascendency as a potential 2024 candidate and top primary rival to former President Donald Trump.

But as he steps out onto the national stage, DeSantis has hit a rough stretch, facing questions about his political strategy, policy stances and personal touch. Some allies have privately expressed concern about his contentious agenda, waffling on Ukraine and reserved response to Trump’s relentless assaults on his record. Several key donors have signaled they may hold back on contributions as he gets his footing. The murmurs reached a crescendo this week when Trump unveiled a series of endorsements from DeSantis’ home state just as the Florida governor traveled to DC to build support for his not-yet announced campaign.

The string of tough headlines continued Thursday morning as his administration scrambled to fire the individual responsible for waking millions of Floridians with a test of the emergency alert system at 4:45 a.m.

The intense scrutiny is illustrative of the expectations facing DeSantis as he positions himself for the biggest challenge of his political career, and it represents the first major test of whether the Florida governor can withstand the chatter and stick to his strategy to knock off the former president.

“Everyone has a plan until they get punched and you have people sort of panicking right now,” one Republican fundraiser in Florida close to the governor’s political operation told CNN.

Despite those concerns, DeSantis remains a formidable political force. His recent travels have attracted scores of Republicans intrigued by the governor’s track record of conservative victories in Florida. Without entering the race, polls continue to show he is currently the candidate most likely to stand in the way of Trump securing a third nomination. And his very presence has helped local Republican groups bring in gobs of money; his appearance in New Hampshire last Friday brought in nearly four times as much for the state GOP than any fundraiser in its history.

Chris Ager, chairman of the New Hampshire Republican Party, said word of the headwinds supposedly slowing DeSantis “just doesn’t match the reality I’m seeing with my own eyes.”

“The more he’s out there talking to people, visiting states, doing retail events like he did in Manchester, all of that misinformation evaporates,” Ager said. “Whatever the real man is will come out and I think we saw some of that Friday night. It was said he wasn’t good at retail and didn’t connect with people. That’s the exact opposite of what I saw.”

Amid those touchstones, DeSantis is not wavering from plans to hold off on launching a campaign until after the Florida state legislature finishes its legislative business next month and a June announcement is more likely, according to people with knowledge of the decision.

“The donor class is extremely concerned,” the fundraiser added. “But (DeSantis’ operation) is moving ahead as planned, believing that if they execute, they’ll be successful, and I don’t think they can be deterred otherwise.”

Meanwhile, the machinery supporting DeSantis’ expected presidential bid is gaining steam without the candidate, including a super PAC that is already building out a field operation and planning to test the boundaries of campaign rules to give the Florida Republican an unprecedented fundraising advantage from the day he announces he’s running.

The super PAC, Never Back Down, has held events in key early voting states as it seeks to erect a fully fledged campaign-in-waiting for Florida’s chief executive. At the same time, the committee – which can raise unlimited sums for its activity from deep-pocketed individuals and corporations – is collecting donations large and small with a goal for DeSantis to break all fundraising records on the day he enters the race, a source familiar with the planning told CNN.

“The former president started early and we want the governor to be competitive and we’re building with that purpose so he’s not starting from a traditional day one,” said Ken Cuccinelli, a former official in Trump’s administration who founded Never Back Down. “We have organizations of this movement put together in the early states and they can pick up and lead from there.”

“It’ll be easier once he’s in,” Cuccinelli added. “And we’re not complaining about it. He has to be governor first.”

Although super PACs technically are prohibited from coordinating their spending decisions with the candidates they support, the early moves by the pro-DeSantis super PAC underscore the changing landscape for presidential campaigns in the years since a pair of federal court rulings – including the Supreme Court’s 2010 Citizens United decision – paved the way for unlimited spending to shape federal candidate elections.

Super PACs traditionally have underwritten political advertising to boost their favored politicians, but that’s an expensive route because independent groups pay a much higher rate for advertising than do candidates. (Under federal law, TV and radio stations are required to offer the lowest advertising rate to candidates.)

Never Back Down has already pumped seven figures into TV advertisements to introduce DeSantis and respond to Trump ads highlighting DeSantis’ past support for privatizing Social Security and Medicare. But the super PAC doesn’t intend to become the advertising arm of the DeSantis political operation. Instead, the group is organizing the kinds of party activists and supporters that campaigns typically mobilize to help run phone banks, knock on doors and organize delegates and caucus-goers needed to capture the nomination. Cuccinelli has already met with local leaders, political operatives and other grassroots organizers in key states.

In 2016, Trump vanquished the well-organized campaign of Texas Sen. Ted Cruz, and the best-funded candidate, former Florida Gov. Jeb Bush. At its most successful, the DeSantis effort would mimic Cruz’s ground game, but with Bush’s money.

In addition to Cuccinelli, who ran Cruz’s delegate operation, Never Back Down has recruited political strategist Jeff Roe, the chief architect of Cruz’s campaign. Meanwhile, DeSantis’ Florida political operation includes veteran election lawyer Charlie Spies, who has pioneered ways for candidates to maximize the use of super PACs in the post-Citizens United era that opened the door to unlimited spending to shape federal elections. Spies served as the legal mind behind Right to Rise, the super PAC that Bush used to raise more than $100 million in the months before formally announcing his candidacy, setting a fundraising record at the time.

A DeSantis political operation is poised to launch with even more money.

The Federal Election Commission, which polices US campaign finance laws, deadlocked last year on a case that centered on whether Rep. Byron Donalds of Florida could transfer money from a state campaign to a federal race. The agency’s inaction in the Donalds case has provided a roadmap for DeSantis and his allies to transfer the $85 million remaining in the accounts of his Florida committee – Friends of Ron DeSantis – to a super PAC, election observers say.

Much of the money is left over from his record-breaking fundraising during his 2022 reelection, but the committee has also brought in more than $12 million since the start of the year, including seven-figure contributions from billionaire GOP donors Jeffrey Yass, Joe Ricketts, John Childs and Jude and Christopher Reyes.

Never Back Down recently announced raising more than $30 million since its launch – giving the Florida governor a potential base of some $115 million months before a formal campaign announcement.

The details on the super PAC’s fundraising won’t become public until July when it files its first disclosure with federal campaign regulators.

In an additional move, Never Back Down is directing DeSantis’ supporters to contribute up to $3,300 – the maximum a candidate can receive from an individual for the 2024 primary – directly to a “Draft DeSantis 2024 Fund.” That money will be transferred to DeSantis’ campaign committee on the day he files to run for office, a source with knowledge of the plans told CNN, with expectations it will be the largest ever first-day sum for a presidential candidate.

In each cycle, candidates and outside groups have increasingly exploited the gray areas of campaign finance law to expand their activities.

In the 2016 presidential campaign, for instance, a super PAC supporting the candidacy of Republican White House contender Carly Fiorina worked to build a campaign infrastructure on her behalf, organizing events and employing staff in early voting states. The Fiorina campaign sought to avoid the appearance of close coordination with the super PAC by posting her schedule publicly on a Google calendar – giving the outside group advance notice of her campaign activity.

“It appears the DeSantis team has learned the lessons from recent election cycles and is now taking advantage of campaign finance laws to maximize his organizational and financial advantages,” said one Republican election lawyer.

However, the strategy is contingent on money continuing to pour into the DeSantis coffers at the pace that allowed him to shatter gubernatorial fundraising records in his last election. Donors have wavered in recent weeks for various reasons – his signing of a six-week abortion ban, his war with Disney over a contentious state law on teaching LGBTQ topics and a general unease about his ability to best Trump.

The growing list of House Republicans from Florida endorsing Trump over DeSantis has added to the unease. The tally reached nine on Thursday as Rep. Michael Waltz – who represents DeSantis’ former congressional district – announced he, too, was supporting Trump.

The episode has exposed what many have long warned is DeSantis’ achilles heel: a lack of people skills. Rep. Greg Steube told Politico that DeSantis has never returned a call during his five years as governor. Nor did DeSantis reach out when Steube seriously injured himself in a tree-trimming accident. Trump did, Steube said.

A source close to one House Republican said that surrogates for DeSantis called members to urge them to stop endorsing before the governor had entered the race. The outreach was poorly received and five Republicans have endorsed Trump since the calls began.

“If the governor wants the endorsement, he should be picking up the phone and calling directly instead of having an aide doing the reach out,” the source close to a House member said. “You know who calls for the Trump endorsement? Trump himself.”

Others, though, have downplayed how much congressional endorsements will matter once DeSantis is in the race.

“It created a good story (for Trump) that Ron went to Washington and got stepped on,” said a Republican operative familiar with GOP fundraising. “But I don’t think sophisticated donors care who (Rep.) Brian Mast is going to support,” the person added, citing one of the Florida Republicans in Congress who endorsed Trump this week.

Even if DeSantis didn’t raise another dollar between now and his launch – an incredibly unlikely scenario – his super PAC would have more money at its disposal than Bush had at the same juncture.

Trump, who has largely relied on small-dollar donors to fill his campaign accounts, “doesn’t have the right message or reach to big donors,” the person added. “There’s a vacuum, and I think Ron is the leader of the race as far as filling the vacuum.”

Within a day of Trump announcing his 2024 White House bid, two billionaires who previously supported Trump – cosmetics heir Ronald Lauder and Blackstone chairman Stephen Schwarzman – said they would not back his candidacy. Another prominent giver, Miriam Adelson – the widow of casino magnate Sheldon Adelson – plans to remain neutral in the GOP primary. Adelson and Lauder had been among the donors to DeSantis’ gubernatorial campaign.

But, in a public blow, another billionaire DeSantis donor – Thomas Peterffy, who founded the electronic trading platform Interactive Brokers – recently told The Financial Times that he was putting his plans to support a DeSantis presidential campaign on hold, citing the Florida governor’s action on social issues, such as signing a ban on abortion after six weeks.

Peterffy declined a CNN interview request through a spokesperson. But he told the Financial Times: “DeSantis seems to have lost some momentum.”

“We are waiting to see who among the primary candidates is most likely to be able to win the general,” he added, “and then put all of our firepower behind them.”