DeSantis, once a rising Republican star, ran a presidential campaign filled with missteps and mistakes

CNN

By Steve Contorno, Jessica Dean and Kit Maher, CNN

(CNN) — In the days leading up to the Iowa caucuses, top advisers to Ron DeSantis steeled themselves for a grim result. The polling that for months told them enough Republicans there were ready to move on from Donald Trump was now predicting that most of them wouldn’t, and they began to consider options for the Florida governor with his political future in mind.

They presented DeSantis with a range of potential outcomes and paths forward. In the event of a dominating performance by Trump, they pitched that DeSantis could bow out, endorse the former president, finish his second term as governor and rebuild his reputation with an eye toward 2028.

He rejected the idea outright, according to a source familiar with the exchange. That was the end of that conversation.

Or so they thought. On Sunday, less than a week after a crushing defeat in Iowa and days before New Hampshire voters are expected to deliver another one, DeSantis bowed out of the 2024 presidential race. In a scripted video statement from Florida, DeSantis endorsed Trump and looked ahead to finishing his second term as governor.

His exit marked a stunning fall for a Republican who for a time appeared singularly positioned to pull the party from Trump’s vice grip. DeSantis once seemed to have it all: money and momentum behind him, a compelling background, a generational argument and a success story to share. Some early polls actually showed him with a lead over Trump.

But what he didn’t have was room for error running up against a popular former president. And the DeSantis campaign made many of them, his advisers, allies and supporters have acknowledged to CNN in interviews.

“Every single thing that could have not gone as we had hoped or planned for went horribly wrong,” one close adviser said.

DeSantis has suggested the race would be different if Trump wasn’t facing four indictments and 91 charges in federal and state courts. Many of his advisers also believe Trump’s legal peril galvanized Republicans just as the GOP presidential contest was about to get underway, closing an opening for an alternative. Former South Carolina Gov. Nikki Haley will attempt to test how wide that opening is in the coming days and weeks.

“I would say if I could have one thing change, I wish Trump hadn’t been indicted on any of this stuff,” DeSantis told the Christian Broadcasting Network in December.

But over a campaign that stretched eight months, there is little DeSantis’ team could point to that they did right – from the disastrous, glitchy kickoff announcement on Twitter Spaces with Elon Musk to the Iowa ground operation that was supposed to overcome Trump’s popularity and arctic weather to deliver a surprise outcome that would shock the country.

It was that final miscalculation that ultimately provided the knockout blow. Not only did the result in Iowa evaporate enthusiasm for his campaign, it also sapped it of credibility. He had promised victory in the Hawkeye State, convinced that the polls hadn’t captured his 99-county tour of the state and insisted the nearly 1 million doors his supporters had touched would be rewarded.

Instead, Iowa revealed how ineffective his effort had been all along — his ground game, his message, his strategy, all exposed as a paper tiger and turning his candidacy into a punchline in Republican circles.

“Historic disaster,” said one veteran Republican fundraiser once hopeful of DeSantis’ chances. “JV team.”

Veteran GOP strategists Curt Anderson and Alex Castellanos called it the “Worst Republican Presidential Campaign Ever” in a blistering audit written for Politico that was devoured Friday by DeSantis allies and enemies alike.

It’s a title DeSantis earned as much for what he squandered as how he fared.

A slow start

DeSantis’ White House bid carried more than just the weight of a political campaign.

“He thinks he’s on a mission from God,” one close confidant described DeSantis’ drive to become president.

It’s an attitude captured in the closing message of his 2022 reelection campaign: A black-and-white video posted to social media by his wife, Casey, that suggested God created DeSantis, “a fighter,” on the eighth day.

After a 19-point reelection victory that November, some in the Republican Party were at least ready to anoint him the inevitable heir to Trump.

“DeFuture,” the New York Post declared the day after, the culmination of two years of Rupert Murdoch’s media empire showering DeSantis with praise for his pandemic contrarianism and cultural battles.

Trump, already a candidate for president once again, was ready for a fight. He called his former ally “an average Republican governor” as the buzz around DeSantis reached new heights and escalated the attacks from there.

But DeSantis, who once donned a Top Gun outfit to declare he would “never back down from a fight,” opted not to punch back. He instead put his focus on the 2023 legislative session in Florida, plotting an agenda of long-sought conservative priorities – universal school choice, a near ban on abortion, fewer restrictions on guns – that would serve as the platform for a policy-oriented presidential campaign. He also escalated his fight with Disney over new state restrictions on teaching sexual orientation and gender identity by taking control of the company’s special taxing district.

He didn’t step foot in Iowa until March to sell his new book. His first earnest swipe at the former president – a dig at the hush money payments allegedly made to adult film star Stormy Daniels – was followed days later by DeSantis defending Trump in the face of an indictment in a New York case related to those payments.

“The war had begun and we were kind of sitting on our backsides,” a source close to the campaign said, describing the time when DeSantis was traveling around the country on a book tour but had yet to formally announce. It left his team unable to push back on his behalf as Trump and his allies pounded the governor, ultimately spending $21 million in ads seeking to define DeSantis when he wouldn’t punch back.

Meanwhile, an emerging super PAC, led by veteran GOP strategist Jeff Roe and Ken Cuccinelli, a former homeland security official in the Trump administration, was given the keys to the DeSantis’ financial coffers. The super PAC, Never Back Down, received $83 million from DeSantis’ former state political committee in a move that a campaign finance watchdog group flagged as potentially illegal, but nevertheless provided an unprecedented financial advantage for the Republican governor.

In an unusual arrangement, Never Back Down was asked to take on many tasks traditionally reserved for campaigns, including training paid canvassers and hosting the governor’s events. Roe and others promised a novel concept that would change presidential campaigns forever.

But Never Back Down’s team of seasoned political consultants clashed immediately with the inexperienced but scrappy Tallahassee team that had just steered DeSantis to a historic gubernatorial victory. The early squabbling, which the media quickly caught wind of, was a precursor to a summer and fall of discontent that ultimately ended with several top staff and advisers leaving acrimoniously, including Roe.

Meanwhile, the Republican donor class that rained six- and seven-figure checks on DeSantis during his reelection bid suddenly had second thoughts. Some voiced displeasure with his contentious second-term agenda and fixation with Disney. Others wanted to kick the tires on other GOP candidates after all.

The DeSantis financial team wrongly assumed the flush times wouldn’t end, and they budgeted for $200 million between the campaign and super PAC at launch with a goal of amassing half a billion dollars by the year. Instead, the super PAC had raised $130 million by June 30 – a historically large amount that nevertheless fell well short of expectations.

“Pick a name,” another fundraiser said. “Every one of them, it was expected they would keep giving.”

His fundraising team downplayed the pull back at the time, with one person telling CNN it would only be a problem if Ken Griffin, the billionaire hedge fund owner who helped bankroll DeSantis’ reelection, decided he wouldn’t donate. They expected $25 million from him.

Griffin ultimately did not give a cent toward DeSantis’ White House bid.

“If you had told me finances would be the problem, I would have hung up on you as needing a mental health check,” the fundraiser continued. “All the dynamics that Trump would be difficult to beat I expected, but I believed there was enough of a coalition of the willing to fund an opposition candidate.”

Ad spending by Never Back Down peaked in mid-April – before DeSantis had officially entered the race.

A glitch-filled launch

By the time DeSantis was ready to announce, his entire political operation was on edge.

“People already felt like it was an uphill battle,” the fundraiser said.

There was a “contentious” debate among DeSantis’s orbit over how best to launch the candidate, with some people pushing for a more traditional announcement from his hometown of Dunedin followed by stops in Iowa and New Hampshire, according to a source familiar with the conversations. But that approach was rejected by the woman who would be announced as DeSantis’ campaign manager, Generra Peck.

Another idea emerged to do something with Elon Musk and X, formerly known as Twitter, which ultimately snowballed into the final idea of the two appearing together on Spaces to broadcast a live announcement. The idea’s supporters argued it was a nontraditional announcement for a nontraditional campaign, according to a source familiar with the discussions.

But donors and other DeSantis allies worried after all the build-up to his candidacy there would be no visual of DeSantis actually announcing his run to air on television stations across the country. A compromise was struck with DeSantis immediately going on Fox News after the Spaces launch to talk about his campaign. An intermediary took the idea to Musk, who agreed.

Musk’s website, though, crashed repeatedly during the announcement, which quickly became the narrative of his introduction as a presidential candidate.

“It could have been cool and successful,” one source familiar with the launch told CNN, “but the glitchiness at the top was perhaps a foreshadowing of the campaign to come.”

Donors gathered in a glitzy Miami hotel for the launch were stunned, and grew more furious when Peck and others tried to spin it as DeSantis breaking the Internet.

As coverage of these early stumbles on mainstream news outlets snowballed, DeSantis stayed inside a right-wing media bubble. He spoke almost exclusively to Fox News, conservative radio stations and right-wing podcasters, ignoring some aides who pushed aggressively for DeSantis to do more with the national media from the very beginning.

DeSantis instead listened to others in his orbit, particularly Christina Pushaw and Bryan Griffin, both of whom joined his campaign from the governor’s office and encouraged him to continue to ignore the mainstream media. He now acknowledges that decision was a mistake.

“I came in not really doing as much media,” DeSantis recently told conservative radio host Hugh Hewitt. “I should have just been blanketing. I should have gone on all the corporate shows. I should have gone on everything.

“We had an opportunity, I think, to come out of the gate and do that and reach a much broader folk,” he added.

Challenges pile up

The abnormalities surrounding DeSantis’ campaign continued to stack from there.

It quickly became apparent that the campaign grew too quickly for its financial situation. In mid-July, the trickle of layoffs began. Meanwhile, DeSantis pulled back plans for a national campaign and refocused his efforts almost exclusively on Iowa.

Yet, as his campaign shrunk, it spent $1.5 million on private planes through September, campaign finance reports show, and held donor retreats at posh locations, like a resort in Park City, Utah.

A bizarre series of events on July 25 illustrated the disconnect. DeSantis flew privately into Tennessee for a fundraiser. Once on the ground, his four-vehicle motorcade was involved in an accident, including the car carrying the governor. That same day, his campaign cut one-third of its staff. And Never Back Down aired its last ad in South Carolina.

Two weeks later, Peck was fired.

Yet, amid the turmoil, DeSantis’ team, led by his top pollster Ryan Tyson, assured donors and operatives that there was an opening in Iowa. Each time they went into the field, their poll numbers showed a growing pool of Republicans open to moving on from Trump. They assumed the surge of support for the former president was a sugar rush from his indictments that would eventually end.

But rather than a coherent message around his candidacy, there was a scattershot of approaches in the ads coming from the super PAC and the campaign. It was largely left up to DeSantis to win over Trump voters through appearances in the state.

Across his 99-county tour of Iowa, DeSantis struggled to articulate a coherent rationale for his candidacy and focused more often on his past accomplishments as a governor than his ideas for the future. He regularly responded to questions from Iowans with actions he took in Florida, rattling off local terms from back home and sometimes leaving crowds perplexed.

His speeches sometimes required a glossary for regular Republicans to understand: woke, ESG, DEI, CRT, Central Bank Digital Currency, social credit scores, Zuckerbucks – all words, phrases and acronyms that were staples of DeSantis’ campaign appearances, media interviews and debate responses.

Still, there were moments when it seemed DeSantis was on the cusp of gaining momentum, such as when Iowa’s popular governor, Kim Reynolds, endorsed him in November.

But that evening also offered a window into his flailing candidacy.

Her involvement represented a momentous coup for DeSantis and a striking break from a tradition from her predecessors. In a stirring speech that night inside a Des Moines event space, she defended her involvement and made an impassioned case for the like-minded conservative governor from Florida.

Yet, during his turn at the mic, DeSantis delivered a largely rote speech filled with familiar lines from his six-month tour of the state, an extended riff off his Florida accomplishments and the “woke” forces he had destroyed. There were only a few passing references to the woman who risked her political capital to back him. He said little that night to suggest he had grown as a politician during his bruising uphill fight for the nomination or had learned much about Iowa or its people despite spending hundreds of hours in the state and meeting thousands of its residents. At times, the crowd could barely muster more than polite cheering.

After stepping off the stage, he shook hands and posed for pictures for 10 minutes from behind a barrier, leaving Reynolds to mingle with his supporters.

The night laid bare the promise and the shortcomings of DeSantis as a presidential candidate. An exacting and relentless leader, DeSantis could execute a game plan as well as anyone but lacked a feel for the campaign trail and struggled to stir a room. He could summon the energy to barnstorm across the state for weeks on end but often appeared disinterested in the people who showed up to hear him.

In the end, a politician who had seemingly done everything necessary to win Iowa – shown up, spent money, secured endorsements – could not win over Iowans.

DeSantis himself acknowledged the limits of the key endorsements he often touted on the trail.

A day before suspending his campaign, he told reporters in Myrtle Beach, “Iowa Republican leadership lined up behind me, and we came in second,” in response to a question about Trump’s new support in South Carolina.

And yet, in the face of this overwhelming rejection of his pitch to Make America Florida, DeSantis refused to change gears. The contours of his stump speech stayed the same as he half-heartedly moved on to South Carolina. Vote for me, he told Republicans there, because I have already done the stuff you supposedly like.

Even in defeat, DeSantis vowed to continue to take on “woke ideology.”

“While this campaign has ended, the mission continues down here in Florida,” DeSantis said as he signed off. “We will continue to show the country how to lead.”

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