'Should we really be doing this?': What went wrong for Ron DeSantis' campaign

In the two weeks since ending his 2024 presidential campaign, Ron DeSantis has returned to Florida and to the duties of his governorship, while still focusing on some of the culture war issues that helped him build a national profile.

At the same time, he's been sharing some intimate, selfie-style videos on social media -- like a conversation with his 5-year-old son about who would win the NFL conference- championship games -- that were rare, if not nonexistent, before and during his presidential run. (His son predicted both winners.)

"Where was this guy during the 2024 campaign?" wrote one social media user, echoing the reaction of other commenters, many of whom were ardent supporters of the governor's presidential run.

DeSantis began 2023 as the best positioned Republican candidate to challenge Trump for the party's presidential nomination, according to polling tracked by 538.

But he begins 2024 as another name on the growing list of rivals who failed to shake the former president's popularity among the GOP -- after his campaign and allied super PAC spent a combined $158,000,000, all to place a distant second in the first nominating contest, in Iowa, before quickly exiting the race.

Among his problems, sources inside and around the DeSantis campaign said, were being hamstrung by the inexperience of key aides, a culture of blinding loyalism, an unusual relationship with his main political group and a strategic failure on how to face the former president who was DeSantis' biggest foe.

"Even if we ran a perfect campaign, I still don't think we would have beaten Trump," one former staffer said.

In interviews with more than a dozen sources close to the campaign -- none of whom would speak on the record, citing professional relationships -- they detailed some of DeSantis' challenges as a candidate as well as what's next for him. (A spokesman for him declined to comment for this story.)

DeSantis' early actions since leaving the race have already sparked speculation that the governor, who is only 45, could make another White House run in the future. A source close to him said that he has privately expressed interest in running again as early as 2028 and has brought it up as a possibility.

DeSantis also plans to keep a small political team around him moving forward, multiple people familiar told ABC News.

His battle with The Walt Disney Co. also reached a recent turning point: A federal judge in Florida earlier this week dismissed a lawsuit filed by Disney against DeSantis and other state officials over the state Legislature's decision to alter the governing structure of the Reedy Creek Improvement District.

Disney had argued in its lawsuit, filed last April, that the change to the district, for which the company was the main landowner, was made in retaliation for criticism of the Parental Rights in Education Act, known by opponents as the "Don't Say Gay" bill. (Supporters of the bill reject that term.)

DeSantis' office applauded the decision to dismiss. Disney, which owns ABC News, is "determined to press forward with our case," a company spokesperson said.

More immediately, said one person close to the governor, he is relishing the break -- pointing to his social media videos.

"He's having fun with it and letting it roll," this person said. "It's hard to be reflective when you're traveling at 200 mph every day on the campaign trail. I think it's him just finally having a free half-hour."

Campaign regrets

Regrets among DeSantis allies about the governor's presidential campaign go beyond his social media presence -- which was dinged as too charmless, too hard-line, too inaccessible, similar to what critics often said, more broadly, about his style as a candidate.

Now in the shadow of his failed bid, multiple sources described strategic, financial and personnel failures during the governor's eight-month run.

DeSantis himself reflected on some of his own missteps shortly before leaving the race.

"I should have gone on everything," he told radio host Hugh Hewitt days before suspending his campaign, referring to a previous decision to avoid many media outlets. "We had an opportunity, I think, to come out of the gate and do that and reach a much broader folk."

DeSantis' first mistake, multiple sources said, was hiring a team of people who were so devoted to him, it sometimes prevented necessary candor.

The governor was surrounded by "loyalists," according to one person familiar with the inner workings of the campaign.

Another source close to the organization told ABC News that team DeSantis was filled with "yes-men" whose fear of telling him things he didn't want to hear ultimately harmed him.

"It felt like nobody was telling the governor the truth," this person said.

A former senior campaign aide who is still close to the governor said that DeSantis "became a better candidate over the course of the campaign" in part due to "his willingness to consider new ideas and perspectives from a wide variety of staff, stakeholders and supporters" -- including, this person said, an increased mainstream media presence after last summer.

One name whom sources brought up repeatedly in interviews with ABC News: Generra Peck, DeSantis' first campaign manager.

Peck guided DeSantis' successful reelection campaign to the Florida governor's mansion in 2022 but did not have experience running a presidential race and, multiple sources said, she overhired and overspent.

The extent of those decisions became publicly evident in mid-July, when the campaign's first filing with the Federal Election Commission revealed it had hired 92 people -- nearly double the next closest candidate's headcount -- and had burned through nearly $8 million in the first six weeks of his campaign, some amount of which went toward, among other expenditures, flying the governor between events in private jets.

Days after that filing, the DeSantis campaign laid off roughly a dozen people, prompting ABC News to ask him whether he had over-hired, a concern he dismissed at the time.

"We don't do consultants so we do everything in house," he said at a news conference in Salt Lake City.

"It's just a different model of doing more in-house than doing consultants," he added. "We'd rather pay salaries for people to perform a function and do it."

Just four days later, however, the campaign announced it had cut over two dozen more people.

The perplexing spending choices by the campaign went beyond staff and travel, multiple sources told ABC News.

Employees reportedly became frustrated when, one day, Peck announced she had purchased a new email system to replace the widely used Microsoft Outlook and demanded the team switch over. According to two sources, Peck would periodically pop into staffers' offices and hunch over desks and reprimand anyone she caught who was still using Outlook and not the newly purchased software.

FEC filings show the campaign paid more than $92,000 to that company for "web service."

"It was less efficient because people didn't know how to use it," a former senior staffer on the campaign said. "How does a campaign manager on a presidential campaign have time to walk around to everyone's office and check their computer screen? I would expect them to be a bit busier than that."

However, one other former senior campaign staffer told ABC News they found the software useful.

Peck was eventually replaced as campaign manager in early August with James Uthmeier, the chief of staff of DeSantis' gubernatorial office, a move that was welcomed by donors and DeSantis allies.

Peck stayed on as a chief strategist.

She declined to comment for this article and has not publicly addressed any criticism.

"Running a presidential campaign is really hard when you're doing it for the first time," a person deeply familiar with the campaign told ABC News. "I think the campaign got better when James became in charge."

'How to attack Trump'?

DeSantis spent the first few months of his campaign reluctant to attack the former president, only throwing punches when asked by voters or the media.

The strategy clearly was not working in building more support for DeSantis or eroding Trump's own standing. Instead, Trump's lead in national and early state polling continued to widen, even as he was under multiple indictments (for charges he denies).

In August, when Trump was charged by special counsel Jack Smith over efforts to overturn the 2020 election, senior DeSantis staffers huddled to discuss how the governor should respond, multiple sources said. DeSantis had seen his numbers decline with each of the other Trump indictments, and some top staff believed a stronger, more aggressive tone toward the former president was needed if the governor was ever going to have a chance in the nominating race.

The meeting got heated, with some senior aides arguing DeSantis should not defend Trump -- while others pushed back, arguing the governor could not afford to upset the former president's base, multiple sources told ABC News.

"Nobody could ever come to an agreement over how to attack Trump," one of the sources said.

Warning signs had been going off among DeSantis aides in the months prior to his official presidential campaign launch in May, the same sources said.

Though the governor was coming off his impressive reelection bid in the fall of 2022, his strongest period of polling began to fade after Trump faced his first indictment in March 2023, as though the Republican base was rallying to Trump over the other options. Some senior aides back then had thought to themselves if it wouldn't be better for the then-popular governor to sit the 2024 campaign out.

But sources told ABC News that the aides were too scared to even mention the option.

"Frankly, there was nobody who would be brave enough to ask, should we really be doing this?" one campaign source told ABC News.

DeSantis, in an NBC News interview not long before he ended his campaign, suggested voters were telling him that he remained a popular No. 2 -- which wasn't enough.

"I had people come up to me saying, 'I love you, man. I'm going to do Trump this time and you next time.' That's not what I wanted to hear, but being there we did make an impression and it's important," he said.

An unusual campaign structure

From the start, the DeSantis team structured its campaign in a way that bucked the precedent for major political bids.

He deferred on key pieces of what would be a standard political operation -- perhaps most notably, many on-the-ground events which he attended -- and his allied super PAC, Never Back Down, which was able to raise unlimited amounts of money but was prevented by law from coordinating with his campaign, instead took over those functions.

"It was presented to us like, 'It's going to change the game and revolutionize how presidential campaigns are done," a senior-level person involved in the campaign told ABC News." We were told, basically, we're outsourcing most of the things the campaign would do to the PAC."

But while the structure was presented as revolutionary, some sources told ABC News that it contributed to headline-making infighting and mishaps on the campaign trail.

At the same time, because Never Back Down was a super PAC, DeSantis could not legally have as much control over how it operated to support him.

Early on, sources said, some staffers were also perplexed by Peck's rate of staffing last year despite her backing a strategy to hand over much of what the campaign did to the political action committee.

"It made no sense why you need to hire 100 people and have them all uproot their lives from other states and come down to Tallahassee -- signed leases, you promised them, like, a stable job -- just to outsource their jobs to the PAC," a person deeply familiar with the campaign told ABC News.

Never Back Down largely took over major parts of what are traditionally campaign operations, pouring millions into the ground game, hosting training sessions, conducting internal polling and releasing memos on strategy -- things that other super PACs do to aid their candidates, but to an extent not seen in other 2024 bids.

By August, with the official campaign struggling financially and having a high cash burn rate, Never Back Down was hosting the vast majority of DeSantis' events, with the governor as a "special guest."

To comply with campaign finance laws, representatives of the super PAC would reach out to the DeSantis campaign to invite the governor to its events. The campaign could either accept or decline the invitations.

DeSantis took part in a total of 180 campaign events in Iowa, with 110 of those events being organized by Never Back Down.

In October, the super PAC carried out all of the governor's campaign events in Iowa, holding a total of 25 that month in the state, while his official campaign held none.

Meanwhile, as part of the normal funds super PACs often set aside for shutdown costs after a campaign ends, Never Back Down also reserved more than $2 million to handle potential legal costs, three sources with direct knowledge told ABC News.

Senior officials for Never Back Down called such a move a normal practice.

"It was just kind of like a general understanding that in the operation of a super PAC, there was a certain small percentage of funds that were set aside to deal with possible legal issues," one of the officials told ABC News.

By the fall, an FEC complaint had already been filed alleging an illegal transfer of funds to Never Back Down from another pro-DeSantis super PAC, but the sources with direct knowledge said the organization anticipated even more challenges, with one source pointing to what they described as an "unprecedented" operation.

In December, a campaign watchdog group filed a complaint with the FEC accusing the campaign and the super PAC of engaging in a "textbook example" of illegal coordination, which DeSantis dismissed as a "farce."

"I mean, give me a break," he told reporters in Cedar Rapids the next day. "Trust me, there's a lot of things that happened that I wish I had control over."

A Never Back Down spokesman said, in part, that they fully complied with the law and the allegations in the complaint were "completely false."

An abrupt ending

Discussions about DeSantis leaving the race, which he ultimately did on Jan. 21, began among him and his staff shortly after he underperformed his goals in Iowa, multiple sources told ABC News.

However, his announcement still surprised some of his allies.

In fact, when DeSantis released his announcement on X, members of his finance advisory board were still planning and developing their finance plan leading into Super Tuesday, one of those members told ABC News.

Roy Bailey, one of the chairs of the board, said the group had been raising money and developing their finance plans, which they believed would have raised millions of dollars that the campaign would be able to use leading into Super Tuesday in early March.

Bailey said that shortly after finding out about DeSantis suspending his campaign, he received a call from the governor, who had this message: Thank you for all the work.

ABC News' Mark Osborne contributed to this report.