Iowa was supposed to be make-or-break for Ron DeSantis. 

The Florida governor essentially moved his campaign there late last year, and Never Back Down, his allied super PAC, spent tens of millions of dollars knocking on doors in the state. 

We’re going to win Iowa,” DeSantis declared on NBC’s “Meet the Press” on Dec. 2. 

But in the week before the all-important caucuses, Scott Wagner, the recently installed head of the super PAC, was doing something that aides found puzzling: He was literally doing a puzzle. 

In the headquarters of Never Back Down in West Des Moines, Iowa, Wagner was, according to some of his staff, spending a significant amount of time in the precious final few days constructing a peaceful 1,000-piece jigsaw puzzle of a landscape.

In a photo taken on Jan. 9, shared with NBC News by a Never Back Down team member, others in the room were hunched over their laptops. 

Everything that went wrong with Ron DeSantis' campaign
Scott Wagner does a puzzle at Never Back Down headquarters in West Des Moines, Iowa.Obtained by NBC News

“Staffers are putting their dedication and devotion to electing Gov. DeSantis and they come in and the CEO, the chairman of the organization, is sitting there working on a puzzle for hours,” said a Never Back Down staffer who was there.

Another Never Back Down staffer also said Wagner worked on it for “hours” in the week before Iowa. 

The fact that one of the top people in charge of securing a win for DeSantis in Iowa was spending time on something unrelated to the caucuses was emblematic of the mismanagement and wasted efforts that many of DeSantis’ own supporters say have plagued the campaign from the very beginning. 

In a comment to NBC News, Wagner noted that the “office puzzle” was “there when we arrived” and “became a sense of pride for the entire team and everyone chipped in a few minutes a piece to get it done.”

“I could not be more proud of every person in our Iowa office. I came out to work with our Iowa team and our incredible COO Jordan Wiggins in person for the final two week push in Iowa and I came away with a group of people I would go to war with any time, anywhere. We worked non-stop together on operations in terrible weather conditions,” he said, adding, “The operation worked nearly 24/7 throughout for the Gov and was absolutely seamless. I am so proud of what we achieved in Iowa and will achieve beyond.”

DeSantis came in second in Iowa, but he was still 30 percentage points behind former President Donald Trump, who captured more than 50% of the roughly 110,000 votes and had a historic margin of victory. Still, DeSantis tried to argue it was a huge win for him — and he has worked to lower expectations in New Hampshire, a state where he was never expected to be a strong competitor.

“I faced a barrage of $50 million attacking me and that — leading into Iowa, and we were able to scrape a second, which, under the circumstances, I think was good. However, Donald Trump posted the victory. So I think he’s benefiting from momentum here,” DeSantis told Fox News during an interview in New Hampshire Friday. “So we haven’t spent very much money here. Nikki Haley is spending an inordinate amount of money here.”

DeSantis is now battling with the former U.N. ambassador to be the last person standing against Trump. But in the early part of 2023, this isn’t where he was supposed to be. DeSantis was widely seen as a formidable governor, a bright star of the Republican Party who could possibly take down Donald Trump — particularly after his landslide re-election victory in 2022. 

Instead, DeSantis is now facing a likely blowout in New Hampshire and massive public polling deficits in most of the early states — a near impossible path forward to hang on in his presidential bid.

NBC News spoke to dozens of DeSantis’ current and former staffers, as well as other supporters, about where the governor went wrong. They painted a picture of missteps from the very beginning: 

  • DeSantis’ campaign hired dozens of staffers in the earliest stages of the race, sapping the operation of much-needed early cash. Within the first two months, 40% of initial hires were fired to conserve resources.
  • A cash-strapped campaign elevated the role of Never Back Down, which promised to spend $200 million boosting his bid but ended up mired in in-fighting that often spun off negative headlines overshadowing the campaign itself. 
  • A near singular focus on culture war fights cost DeSantis donor support, as many of the biggest anti-Trump GOP donors who originally supported him eventually decided to give to other candidates or sit out the 2024 election cycle. 
  • DeSantis’ decision to wait for six months after his massive re-election win to announce his run for president cost him valuable momentum.

NBC News reached out to both the DeSantis campaign and Never Back Down for comment for this piece.

A DeSantis adviser said that while the campaign did make a number of blunders, in the end, none of that may have been enough to overcome Trump. 

“I think you have a combination of strategic errors throughout along with bad, bad early management, along with a candidate just too set in his ways,” said the adviser, who was granted anonymity because they still work for him. “At the end of the day, I would say that all mattered less than Trump. He was an overall force of nature. For all the Monday morning quarterbacking that is coming, I don’t know a scenario where he would have lost.”

‘I knew they were stupid’

DeSantis’ presidential campaign was a mess from the moment it launched.

The Florida governor decided to do something different from the usual tightly choreographed announcement speech: He turned to the unpredictable social media platform once known as Twitter. 

DeSantis’ May 24 rollout was widely panned and full of glitches. Twitter’s servers apparently couldn’t handle the traffic, and the Twitter Spaces app repeatedly crashed. The event with CEO Elon Musk was audio-only — depriving the candidate of photographs he could use in ads and fundraising pitches — and by the time of DeSantis’ big announcement, much of the audience had clicked away. 

It was intended to bolster his support with right-wing Twitter users, but the tech issues dominated the day. 

Even at the time, doubts were starting to creep up. Not everyone in DeSantis’ inner circle agreed with the decision to launch with Musk. 

“When they decided to do the Twitter Spaces launch, maybe then at that point, I knew they were stupid,” one former Never Back Down adviser told NBC News. 

And after the failed launch, supporters — and even some of its staffers — started to wonder whether the campaign was the juggernaut it had promised to be. 

“What harmed the campaign the most off the bat was that it didn’t have a clear purpose and message,” a former DeSantis campaign staffer said. “No one really could articulate ‘why Ron.’” 

“We were never given any idea of what the message we should be pushing was,” one early DeSantis social media personality said of the campaign’s lack of communication and strategy. “It was a mess from the start.”

The fight club

It was just two weeks into the campaign, and already, the squabbling had begun.

The campaign’s top brass, including then-campaign manager Generra Peck, top adviser Ryan Tyson and Christina Pushaw — who was the architect of DeSantis’ communications strategy — held a conference call with those tapped to be the social-media knife fighters on DeSantis’ behalf. The group of roughly a dozen influencers was informally dubbed the “fight club” by the campaign. They were willing to combat members of the media and DeSantis’ political foes, but from the very early weeks of the campaign, many were flummoxed by leadership’s direction, or lack thereof. 

“The conference call was a sh– show, just an absolute sh– show,” said a former fight club member who was on the call. “People [top staffers] were pressed on the message and, especially after the failed rollout, they had no answers.”

During a particularly bizarre portion of the meeting, Bill Mitchell, a DeSantis supporter with a large social media following, asked the top DeSantis campaign staff if they could call Musk because he was concerned that the site was limiting visibility of his posts — a practice commonly referred to as “shadow banning.”

“He cut me off — I’ll remember this to my dying day — and asked the top people on the campaign if they could call Elon Musk and ask why he is being shadow banned,” a second person on the call recounted. “That was the level of people we were working with. It was just kind of embarrassing to a point.”

Mitchell did not return a request for comment.

The call is a snapshot of what some of even DeSantis’ closest advisers viewed as a campaign that was chaotic, rudderless and often without a coherent message. And when a message would briefly emerge, they told NBC News, it was often washed out by a tidal wave of self-inflicted negative headlines.  

This pattern would play out over and over on the campaign. In early December, when DeSantis finally completed his tour of all 99 counties in Iowa — a moment that should be nothing but good press — he instead had to deal with turmoil at Never Back Down, which was then naming its third CEO in two weeks.  

The organization was set up to fund a massive ground game, but as the official campaign started to run low on cash it became the driver for nearly all campaign activities, including coordinating events and running TV ad campaigns it never expected to have to fund.

Chaos sets in

The internal messaging chaos in the beginning was happening as the campaign also grappled with massive early spending problems exacerbated by Peck’s decision to hire dozens of staffers much earlier than normal. Roughly 40% of those initial hires were let go just two months into the race.

“They realized the finances were a train wreck,” one DeSantis adviser said. “She built a juggernaut for the general election without considering they had a primary to get through.”

Peck was out by August, just three months into the campaign, in another in what had become a long line of debilitating “resets” that helped define DeSantis’ early efforts. Peck declined to comment for this piece. 

DeSantis’ camp realized its early “long-haul” strategy to map out a plan going deep into the primary season was not sustainable after it stumbled out of the gate, and officials quickly shifted their focus and resources to Iowa. 

Never Back Down spent tens of millions of dollars building a ground game that ultimately included 1,500 precinct captains. It’s that intense focus that makes DeSantis’ significant loss in Iowa so damning to his ability to project viability moving forward. 

Several people interviewed by NBC News also pointed to the nearly seven months between DeSantis’ re-election victory in November 2022 and the late May launch of his presidential campaign. 

“It was a total failure to launch,” one former DeSantis adviser said. “This thing blew up on the launch pad. They had six months to get ready for very serious strategic questions, the most important of which was how to deal with Donald Trump. They had no answers. We are nine months in, and they still have not figured it out.”

Some in DeSantis’ early political orbit did press him to attack Trump from the get-go because they thought there was no way to beat him without engaging, but DeSantis’ inner circle had other ideas. There was a continued belief that the support at that time was “soft” for Trump and that if DeSantis did not anger Republican primary voters who previously supported Trump, those supporters would come over to them.

This lack of strategy dealing with Trump played out early on — even before his presidential launch — when DeSantis commented on a possible Trump indictment in New York. 

He criticized the investigation there as politically motivated, but he also repeated the allegations — albeit without naming the former president. 

“​I don’t know what goes into paying hush money to a porn star to secure silence over some type of alleged affair, I just, I can’t speak to that,” he said at the time, a swipe that was seen as clumsy and criticized by both Trump allies and critics. 

The former Never Back Down adviser said this was the first point at which they became concerned that there might be problems. 

“If you’re going to pick a fight, pick a fight,” this person said. “Don’t throw a punch and then run away and say you’re not fighting. … He had no idea how to be a candidate.”

‘Losing Ken was big’

An early indicator of what would become DeSantis’ campaign trajectory was when hedge fund billionaire Ken Griffin decided he would no longer be backing DeSantis after he had given $10 million to his past gubernatorial campaigns. DeSantis’ heavy focus on culture war fights, Griffin said, eventually turned him off.

“Losing Ken was big,” a DeSantis donor said. “And the bigger problem was it sent a signal to others.”

As Haley began to strip supporters from DeSantis and his poll numbers stagnated, money became a significant struggle. DeSantis reported raising more than $20 million for his campaign during his first reporting period, but that number came with some flashing red lights — including the huge number of donors who had already given the maximum amount of money legally allowed. 

After that first wave of cash flowed into his official account, DeSantis struggled to raise money directly for his campaign. Instead, he relied on the Never Back Down super PAC to fund much of his early operations. The dynamic raised questions about the legality of using a super PAC, which can not legally coordinate with a campaign, to run most important functions, including the campaign’s ground game, most events and a bus tour that took DeSantis to all 99 counties in Iowa.

“Never [Back Down] PAC has for months coordinated its activities with and made in-kind contributions to DeSantis and his campaign committee, contravening the explicit legal requirement that super PACs must remain ‘independent’ of—i.e., not coordinate with or make contributions to—federal candidates or their campaigns,” the complaint filed with the Federal Election Commission stated,” read a complaint filed in December by the Campaign Legal Center.

A veteran Florida-based Republican operative who did not work for DeSantis said that he had conversations with those who did work for Never Back Down about being careful of the appearance of coordination.

“Yeah, there were those of us warning people who got involved with them late that it’s a good idea to try and stay away from Never Back Down,” a veteran Florida GOP operative said. “It was clear they were playing with fire, and got much closer to — if not clearly — surpassing the fire wall you’re not supposed to go past. It’s a dangerous situation, and I’m not sure if Trump gets elected that his Department of Justice won’t come knocking.”

“He’s not going to let DeSantis off the hook for anything,” the person added.

The attempt to fund a presidential campaign almost exclusively through a super PAC was a fairly novel concept, and one that gave outsized power to Jeff Roe, a longtime Republican political operative who became a controversial figure as he continued to get in squabbles with members of the super PAC who were perceived to be closer to DeSantis’ inner circle. 

It created a sort of Tallahassee vs the world dynamic, with DeSantis’ greatest amount of trust left in the hands of the consultants and operatives he had known the longest. No one in that group, however, had ever been involved in a presidential campaign. That team initially tried to replicate the playbook for DeSantis’ massive 2022 re-election win, a move that seemed naive to outsiders brought in early in the campaign.

“The blunt truth is that DeSantis’ presidential campaign was sabotaged through early incompetence in Tallahassee,” the person said. “There was a brief chance to reset things, but additional missteps mortally wounded the campaign in its infancy.”

Conversely, there was a growing sense among other DeSantis advisers that Roe and Never Back Down wasted more than $100 million in donor cash with little to show for the effort.

Eventually the power struggle started to center on Roe versus Wagner, the South Florida attorney and longtime DeSantis ally who sat on the group’s board. NBC News reported the two openly feuded at times before Roe finally left the organization he helped build in mid-December. 

The difference between the Tallahassee set and the wider Never Back Down world often played out in media interactions, with the former significantly more distrustful of engaging with the traditional press.

But DeSantis has already started to look back on his campaign and admitted that some things could have been done differently — including adjusting the earlier strategy of shunning much of the media.

“I came in not really doing as much media. I should have just been blanketing,” he told conservative host Hugh Hewitt Thursday. “I should have gone on all the corporate shows. I should have gone on everything. I started doing that as we got into the end of the summer, and we did it. But we had an opportunity, I think, to come out of the gate and do that and reach a much broader folk.”

Knock, knock

Never Back Down banked on a massive door-knocking effort being the lynchpin of an effort to dethrone Trump. It was so confident in the plan that it invited reporters to Iowa to show off its training center there

It didn’t work.

Three people who worked on the door-to-door effort in early states told NBC News they ran into staunch resistance from Trump voters who showed no sign of budging. They also said the super PAC focused too heavily on targeting rural voters as opposed to zeroing in on the suburbs, which may have been warmer to DeSantis’ campaign. And by dispatching door-knockers from all over the country, the effort lost the kind of local feel that grassroots activists said is key to a successful canvassing campaign.

“I’m not saying it’s not possible, but most of these guys that are getting down off of their tractor, when our guys pull it up on their property, they’re voting for Trump,” one person who formerly worked on the effort said. “And they’re not going to change their mind.”

As of late last month, Never Back Down boasted of knocking on nearly three million doors across Iowa, New Hampshire and South Carolina. Jess Szymanski, a spokesperson for the PAC, said DeSantis’ opponents would “stop at nothing to undermine the fact that we’ve built the largest, most advanced grassroots and political operation in the history of presidential politics.”

What’s next?

Headed into New Hampshire, DeSantis was polling in the single digits and Trump had a commanding lead in South Carolina, a state where Haley previously served as governor and held a significant lead over DeSantis in most public polling.

Now, DeSantis’ best path to the nomination isn’t through Trump, but around him. Three people in DeSantis’ orbit told NBC News that the most logical path for the governor of Florida, at this point, is to block Haley from winning in New Hampshire, beat her in South Carolina and position himself as the clear lead alternative to Trump in the event his legal peril or age prevents him from making it to November.

“I think that’s the case,” a DeSantis supporter said. “He believes there are multiple scenarios where Trump wouldn’t be the nominee.”

A second DeSantis ally said they’re “not totally convinced” it’s not a good idea for DeSantis to “stay in as long as humanly possible just because of the unknown that is Trump in his situation.”

“Their path forward is to stay in and hope that something either legally, or from a health perspective, occurs that removes Trump from the race,” the person who was involved with the Never Back Down effort said. 

In any case, the campaign and its aligned committees are on cash fumes, a point made clear by the fact that it did not have any TV ad reservations in New Hampshire or South Carolina in the closing weeks of January, and had drastically scaled back its ground game efforts in both states.

In another sign of dysfunction, a person who was involved with the Never Back Down effort — and who still supports the governor — said that in recent days, a staffer tried to contact a firm to buy lists of voters in South Carolina. The problem was they already had voter lists in that state.

“They were trying to buy the file from a different company because either they don’t know that they own it or they don’t know how to access it and they’re afraid to ask,” the person said. 

The campaign, at times, felt like it was starting to ramp down even as DeSantis and his team tried to continue to project a long-haul strategy they likely could not afford to executive unless Haley drastically underperformed in both South Carolina and New Hampshire. 

Even before Iowa, there was a sense of resignation setting in over large swaths of the DeSantis’ campaign and aligned super PACs, but after his drubbing in that first-in-the national nominating contest, an exhaustion and hope for the end started to settle in amongst his top advisers.

DeSantis spent months plotting out a presidential campaign on the heels of his 2022 win, and he had all the momentum and the money as the 2024 election cycle started in earnest. But none of those best-laid plans came to fruition.

“Hopefully, it’ll be over soon,” the operative who formerly worked on the Never Back Down effort said. “I’m just really tired of all the infighting and all the folks going back and forth about this. It’s done. He’s not going to win it. If you are serious about not wanting Trump to be the nominee, as much as it pains me to say this at this point, I think all the energy goes to Nikki Haley. And I guess you try to ride that train.” 

“But,” they added, “that’s probably not going to work out too well, either.”

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