What Went Wrong for Ron DeSantis in 2023

Gov. Ron DeSantis of Florida woke up in Iowa with a familiar political headache.

The man he is chasing in the polls, Donald J. Trump, had just been disqualified from the ballot in Colorado in yet another legal assault that Mr. Trump leveraged to cast himself as a victim. And so Mr. DeSantis trod carefully the next morning outside Des Moines when he called Mr. Trump a “high-risk” choice, alluding to “all the other issues” — 91 felony counts, four indictments, the Colorado ruling — facing the former president.

“I don’t think it’s fair,” Mr. DeSantis said. “But it’s reality.”

He was talking about Mr. Trump’s predicament. But he could just as easily have been talking about his own.

Boxed in by a base enamored with Mr. Trump that has instinctively rallied to the former president’s defense, Mr. DeSantis has struggled for months to match the hype that followed his landslide 2022 re-election. Now, with the first votes in the Iowa caucuses only weeks away on Jan. 15, Mr. DeSantis has slipped in some polls into third place, behind Nikki Haley, and has had to downsize his once-grand national ambitions to the simple hopes that a strong showing in a single state — Iowa — could vault him back into contention.

For a candidate who talks at length about his own disinterest in “managing America’s decline,” people around Mr. DeSantis are increasingly talking about managing his.

Ryan Tyson, Mr. DeSantis’s longtime pollster and one of his closest advisers, has privately said to multiple people that they are now at the point in the campaign where they need to “make the patient comfortable,” a phrase evoking hospice care. Others have spoken of a coming period of reputation management, both for the governor and themselves, after a slow-motion implosion of the relationship between the campaign and an allied super PAC left even his most ardent supporters drained and demoralized.

The same December evening Mr. DeSantis held a triumphant rally in celebration of visiting the last of Iowa’s 99 counties — the symbolic culmination of his effort to out-hustle Mr. Trump there — his super PAC, Never Back Down, fired three of its top officials, prompting headlines that undercut the achievement.

The turmoil at the super PAC — which followed a summer of turbulence inside the campaign — has been almost too frequent to be believed. The super PAC’s chief executive quit, the board chairman resigned, the three top officials were fired and then the chief strategist stepped down — all in less than a month, enveloping Mr. DeSantis’s candidacy in exactly the kind of chaos for which he once cast himself as the antidote.

The New York Times interviewed for this article more than a dozen current and past advisers to Mr. DeSantis and his allied groups, most of whom spoke on condition of anonymity to discuss a candidate they still support and a campaign that is still soldiering on. Those advisers paint a portrait of a disillusioned presidential candidacy, marked by finger-pointing, fatalism and grand plans designed in a Tallahassee hotel in early spring gone awry by winter.

Cash is scarce as the caucuses near. Never Back Down, which spent heavily to knock on doors in far-flung states like North Carolina and California last summer, canceled its remaining television ads in Iowa and New Hampshire on Friday, though new pro-DeSantis super PACs are picking up the slack.

Federal records show that, by the time of the Iowa caucuses, the DeSantis campaign is on pace to spend significantly more on private jets — the governor’s preferred mode of travel — than on airing television ads.

Andrew Romeo, Mr. DeSantis’s communication director, denied the governor’s candidacy was in disarray. In addition, the campaign provided a statement from Mr. Tyson denying his remarks about making the patient comfortable.

“Different day, same media hit job based on unnamed sources with agendas,” Mr. Romeo said. “While the media tried to proclaim this campaign dead back in August, Ron DeSantis fought back and enters the home stretch in Iowa as the hardest working candidate with the most robust ground game. DeSantis has been underestimated in every race he’s ever run and always proved the doubters wrong — we are confident he will defy the odds once again on Jan. 15.”

Mr. DeSantis, in other words, is still hoping for a turnaround in 2024. This is the story of how he lost 2023.

Miscalculations, mistakes and missing the moment

The governor started the year as the undisputed Trump alternative in a Republican Party still stinging from its unexpected 2022 midtermlosses.

But behind the scenes, the DeSantis candidacy has been hobbled for months by an unusual and unwieldy structure — one top official lamented that it was a “Frankenstein” creation — that pushed the legal bounds of the law that limits strategic coordination and yet was still beset by miscommunications.Those structural problems compounded a series of strategic miscalculations and audacious if not arrogant assumptions that led to early campaign layoffs. Profligate spending and overly bullish fund-raising projections put the campaign on the financial brink after only two months.

The candidate himself, prone to mistrusting his own advisers, did not have a wide enough inner circle to fill both a campaign and super PAC with close allies, leaving the super PAC in the hands of newcomers who clashed with the campaign almost from the start.

Mr. DeSantis’s decision to delay his entry into the race until after Florida’s legislativesession concluded meant he was on the sidelines during Mr. Trump’s most vulnerable period last winter. Then, once Mr. DeSantis did hit the trail, he struggled to connect, appearing far more comfortable with policy than people as awkward encounters went viral.

“You’re running against a former president — you’re going to have to be perfect and to get lucky,” said a person working at high levels to elect Mr. DeSantis and who was not authorized to speak publicly. “We’ve been unlucky and been far from perfect.”

In Mr. Trump, the governor has also found himself running against a rival who filled the upper ranks of his operation with veteran consultants that Mr. DeSantis had discarded. The Trump team used its insider knowledge of his idiosyncrasies and insecurities to mercilessly undermine him, from his footwear to his facial expressions, starting months before he entered the race.

Mr. DeSantis tacked to the right to win over Trump voters, undercutting his own electability case with hard-line stances, including on abortion. For many Republicans, President Biden’s weak standing tempered any urgency to pick a so-called electable choice. And when the debates began, Mr. DeSantis underperformed initially in the bright glare of the national spotlight.

Remarkably, in a race Mr. Trump has dominated for eight months, it is Mr. DeSantis who has sustained the most negative advertising — nearly $35 million in super PAC attacks as of Saturday, more than Mr. Trump and every other G.O.P. contender combined.

Among other early errors: The DeSantis team had penciled in that Ken Griffin, the billionaire investor, would give his super PAC at least $25 million and likely $50 million, according to three people familiar with the matter. Mr. Griffin neither gave nor endorsed, and by the fall, the super PAC’s chief strategist, Jeff Roe, had recommended searching for more than $20 million in spending cutbacks — a remarkable budget shortfall for a group seeded with $100 million only months earlier.

Never Back Down bragged about knocking on two million doors by September — but more than 700,000 were households outside the key early states of Iowa, New Hampshire and South Carolina.

Mr. DeSantis’s popularity rose during the coronavirus pandemic because he made enemies of the right people — in the media, at Martha’s Vineyard, at the White House — clashes that were invariably amplified by conservative news media. Suddenly, he found himself in the cross hairs of the country’s most popular Republican.

“I used to think in Republican primaries you kind of could just do Fox News and talk radio and all that,” Mr. DeSantis told the Iowa conservative news host Steve Deace in October. “And, one, I don’t think that’s enough but, two, there’s just the fact that our conservative media sphere, you know, it’s not necessarily promoting conservatism. They’ve got agendas, too.”

Running against a former president would require an insurgent campaign. But Mr. DeSantis had grown accustomed to the creature comforts of the Tallahassee governor’s mansion, where a donor had installed a golf simulator for him, and even his rebranded “leaner-meaner” campaign that slashed one-third of his staff wouldn’t give up private jets.

Some allies still hope Never Back Down’s door-knocking will carry the day in Iowa, reinvigorating his run by defying ever-diminished expectations. Of late, Mr. DeSantis has resorted to parochial pandering, promising to relocate parts of the Department of Agriculture to the state.

“He’s come into his own now — it took a while,” said Mr. Deace, who supports Mr. DeSantis and campaigned with him in recent days. “The question is now: Is there enough runway to manifest that on caucus night?”

From the start, the DeSantis theory had been that undecided Trump supporters would have one other ideological home, with a governor running as an unabashed Trump-style Republican. Once Mr. DeSantis was the only Trump alternative, the thinking went, the smaller anti-Trump faction would come along to forge a new majority.

But after the first indictment, soft Trump supporters returned en masse to the former president. And Mr. DeSantis soon lost ground to Ms. Haley in courting the moderate anti-Trump wing.

His standing in national polling averages has steadily declined, from above 30 percent in January 2023 to close to 12 percent today.

Mr. DeSantis himself has begun to look back at what might have been. “If I could have one thing change, I wish Trump hadn’t been indicted on any of this stuff,” Mr. DeSantis recently told the Christian Broadcasting Network. “It’s sucked out a lot of oxygen.”

Some questioned the wisdom of running even before the campaign began. Shortly after Mr. Trump was indicted in late March, as Republicans rallied around the former president, one adviser called Mr. DeSantis’s soon-to-be campaign manager, Generra Peck, to suggest that maybe this cycle was not his time.

The concern was quickly dismissed.

A closed-door strategy session

The DeSantis team had banked more than $80 million by the spring of 2023 — left over from his re-election effort — and needed to figure out how to use it.

Federal law did not allow a direct transfer to a campaign account. So they decided to fund an allied super PAC that would be led by Mr. Roe, a polarizing operative who had managed the presidential campaign of Senator Ted Cruz of Texas in 2016, and served as a top strategist for Gov. Glenn Youngkin of Virginia. Ms. Peck told people at the time that recruiting Mr. Roe would help keep those rivals, especially Mr. Youngkin, on the sidelines. It didn’t hurt either that Mr. Roe had led Mr. Cruz to win the Iowa caucuses.

The first week of April — days after the first Trump indictment — all the top strategists involved in Mr. DeSantis’s soon-to-be presidential campaign gathered inside a conference room at the AC Marriott in Tallahassee. On one side of the table was the team that would eventually run his campaign, led by Ms. Peck. On the other were the operatives running his allied super PAC, led by Mr. Roe and the super PAC’s chief executive, Chris Jankowski. One person, David Polyansky, attended the meeting as a super PAC official but later became the deputy campaign manager.

Then there were the lawyers, patched in by phone to make sure the conversation did not veer into illegality. Federal law prohibits campaigns and super PACs from privately coordinating strategy but technically, at that moment,there was no formal Ron DeSantis presidential campaign. A goal of the April 6 gathering, which has not previously been reported, was to establish what the DeSantis team called “commander’s intent” — a broad vision of responsibilities in the battle to come.

The two sides even exchanged printed memos about hypothetical divisions of labor in a would-be 2024 primary. The upshot: The campaign would focus on events in the early states, and the super PAC would organize March contests, and invest in an unprecedented $100 million ground operation across the map. The super PAC was also expected by the DeSantis team to raise huge sums from small donations online, and direct them to the campaign. That program would go on to raise less than $1 million.

The close ties between Mr. DeSantis’s campaign and Never Back Down have already prompted a formal complaint from a watchdog group that accuses the relationship of being a “textbook example” of coordination that is illegal under campaign finance laws.

In late May, Mr. DeSantis formally entered the race in a glitch-plagued Twitter announcement that came to symbolize his struggles. Relations with the super PAC were soon just as troubled.

In Tallahassee, the campaign team could not understand why the super PAC was positioning itself so prominently in news stories. When Mr. Roe said in late June that