How Trump dominated Iowa — and held back DeSantis and Haley

DES MOINES — Donald Trump recently began telling dinner guests at Mar-a-Lago about a haunting memory from the 2016 Iowa caucuses.

His daughter Ivanka and her husband, Jared Kushner, had shown up to speak at a Des Moines caucus site, not really understanding what to expect. They discovered a Trump campaign in disarray, without organized volunteers or staff.

“Daddy, I don’t think you’re going to win,” Trump recalled Ivanka telling him in a phone call that night, according to someone who heard the story more than once. “These people don’t know what they’re doing.”

Sen. Ted Cruz (R-Tex.), powered by a high-tech turnout machine, defeated Trump that night, causing the furious future president to call for his first election do-over. Cruz “illegally stole it,” he falsely claimed.

But as Trump told the story to friends and aides late last year, it took on a new meaning. Trump signaled that he had come to accept his 2016 Iowa loss — and that he was singularly determined not to be embarrassed again. “It’s the only time I had a minor defeat,” he told a crowd a few weeks ago in Ankeny, Iowa, ignoring other losses, including the 2020 election. “But I learned a lot.”

The point of Trump’s tale was that he would approach 2024 differently, a strategy that succeeded Monday night when he won the favor of 51 percent of caucus-goers, more than twice the share he scored eight years ago. He trounced Florida Gov. Ron DeSantis (R) by 30 points and former U.N. ambassador Nikki Haley by 32 points.

Iowa had once again succeeded in its historical role, pruning an unwieldy field of nine major candidates down to a dominant front-runner and two remaining challengers with very different paths ahead of them.

For Trump, the night produced an ideal result, forcing DeSantis to underperform his own ambitions while denying Haley the clear boost she sought before the New Hampshire primary, where she now polls within striking distance of Trump. Both vowed to stay in the race, while neither could claim to have consolidated the Trump opposition behind them.

Top strategists for each of the three campaigns, many of whom spoke on the condition of anonymity to talk frankly about their experience, described the road to the Iowa result as a grueling one, filled with major miscalculations, surprise indictments, psychological warfare and internal campaign squabbles.

The former president proved he could learn to play a game he once ignored. The all-star Florida governor struggled with a national-league learning curve. And the former diplomat overcame long odds with a big bet on her own charisma. The race had begun.

“I want to congratulate Ron and Nikki for having a good time together,” Trump declared with sarcasm in his victory speech Monday night. “We’re all having a good time together.”

As the caucuses approached, DeSantis made a point of outworking his opponents, with more events, more time taking questions and a buzzing ground operation he and his allies had been building longer than anyone else. No GOP campaign had ever invested more, earlier in the state, with a small army of paid canvassers knocking Republican homes about 1 million times and the eventual endorsement of the state’s popular governor, Kim Reynolds (R).

But in the final weeks, a gloom hung over his operation. A leader in Iowa of the DeSantis super PAC, Never Back Down, greeted anyone who flew in with the same warning: Focus on the work. “Anyone who comes here with a negative attitude, I don’t need you,” newcomers were told.

DeSantis had started with a grand plan to compete across the country, launching summer paid canvassers in states such as Texas and California. But in the end, Iowa was their last stand, and he was polling 10 points lower than where he had started in the high 20s.

From the beginning, the effort was hobbled by major miscalculations, competing advisers, wooden interactions with voters and a series of indictments against the former president that DeSantis could not control, his staff and confidants quietly admitted.

DeSantis waited nearly 200 days after his big 2022 reelection win to make his campaign official, giving Trump time to drive his poll numbers down. His campaign launch on X — a decision DeSantis made at the last minute after talking with Elon Musk — crashed, dismaying donors and allies. He started slow, largely limiting his media outreach to conservative networks like Fox News that he later said would abandon him.

“He missed his moment,” one person close to the governor later concluded, a sentiment shared by five others in touch with him or his campaign.

Some of the big donors the governor had bet would fund his effort, such as billionaire hedge fund magnate Ken Griffin, grew frustrated with his initial rollout, including a policy shift to the right on Ukraine and abortion. A $20 million donor to Never Back Down, Robert Bigelow, complained publicly about DeSantis’s support for a six-week abortion ban. As Bigelow later told Trump and his advisers, DeSantis never called to address his concerns. The Nevada businessman, who did not respond to a request for comment, switched his support to Trump.

By summer, the DeSantis campaign was approaching insolvency, prompting what one aide feared was a “Scott Walker situation,” referring to the once-high-flying Wisconsin governor whose 2016 campaign went broke after a couple of months. DeSantis was criticized even by some people close to him for extensively using private planes while making other cuts, forcing a revamp of the plans for both his own campaign and Never Back Down, which abandoned its national effort.

A group of allies and advisers had an intervention of sorts with the candidate at a ski lodge in Park City, Utah, in July. DeSantis installed as his second campaign manager his longtime gubernatorial chief of staff James Uthmeier, who announced at a staff meeting on his first day that anyone caught leaking would be fired on the spot.

But the public airing of internal drama would only get worse. People close to DeSantis described searching in vain for messages against Trump with focus groups — his comments about abortion, his failure to finish the border wall or overturn Obamacare. All the while, Trump trounced the campaign in news coverage, an advantage that DeSantis’s team tracked closely. Even when DeSantis did a televised town hall, “half of that event is still [Trump’s] because the questions are about him,” a DeSantis adviser said.

“The indictments crushed us,” said one person who regularly talked to DeSantis. “We sort of joked that he needed to get a mug shot to compete with Trump.”

The setbacks exacerbated a flaw in the DeSantis campaign’s architecture. He had few close confidants who knew him well beyond his wife, and he sometimes distrusted experts who told him what to do. His operations were run instead by competing fiefdoms, including major parts of two Republican consulting empires, Jeff Roe’s Axiom Strategies and Phil Cox’s GP3 network of companies. Both answered to a shifting third group of aides in Tallahassee.

In practice, the arrangement gave everyone someone to blame as the effort stumbled, with no one taking responsibility for the failures. The Tallahassee team was furious with stories of discord at the super PAC, while the super PAC kept finding its mission changed to compensate for the failures of the campaign. Cox moved in and out of both worlds.

DeSantis loyalists and campaign officials said they didn’t trust some super PAC staff and voiced frustration that the outside group was not spending more to attack Haley. Some pushed for the creation of a new PAC, called Fight Right. Top Never Back Down officials — two CEOs, a board member, Roe and other staff — resigned or were fired.

“What really do we have to lose?” said one person close to the campaign. “If you’re going to go, you know, leave it all on the battlefield; you have to trust the full team.”

But the late disorder did have a cost. DeSantis’s foes shifted millions in television ads to highlight the dysfunction, aiming to undermine his campaign’s closing message of competence — “No Excuses, Just Results.”

Internally, the new structure also failed to end disagreements, as the outside group’s remaining advisers battled over what ads were working and how to measure their effectiveness. Some viewed the attack ads run by the new group, Fight Right, as helping Haley more than they hurt her, as her polling support rose while her favorability rating fell.

“The original leadership that was established by the governor and his team at Never Back Down had a plan that if it was implemented was headed to success,” said one person familiar with the effort from the beginning. “But unfortunately, the changes that began with the reorganization of the board in October changed our trajectory.”

Another person involved in the effort dated the problems to personnel decisions at the start of the campaign, suggesting the governor did not adequately prioritize “competence and loyalty.”

Fight Right, for its part, took credit for keeping Haley from overtaking DeSantis, an outcome that could have been catastrophic given his investments in the state. “When Iowa Republicans learned the truth, Nikki’s favorables plummeted and she had to enlist Iowa Democrat support in her failed attempt to ‘punch her ticket out of Iowa,’” Taryn Fenske, a spokeswoman for the group, said in a statement.

DeSantis told some conservative activists that having the backing of Reynolds and evangelical organizer Bob Vander Plaats would guarantee significant support in Iowa, according to a person familiar with the conversations.

DeSantis tried to stay upbeat, telling allies that he would keep his campaign going no matter what, predicting that Trump’s legal troubles would make it more difficult for him and that Haley could not win her home state of South Carolina. In the final days in Iowa, he privately predicted to allies that he could still win, and he relied on dozens of Florida volunteers, including lobbyists and lawmakers, who flew in and turned the Sheraton in West Des Moines into a Tallahassee reunion spot.

One of the lobbyists, a Tallahassee stalwart, posted a picture of his black Jeep Cherokee broken down in the snow on the side of the road. “Rental has an ice scraper, but no shovel,” he wrote.

With polling showing DeSantis in the single digits in New Hampshire and with half of Haley’s vote in South Carolina, his finance team focused Tuesday on finding a way to refill his coffers for the long road ahead — and allies conceded the polling in New Hampshire has been mixed at best. Unlike his rivals, DeSantis has abandoned his television ad campaign for next week’s New Hampshire primary.

“While it may take a few more weeks to fully get there, this will be a two-person [race] soon enough,” DeSantis campaign spokesman Andrew Romeo said in a statement. “Despite spending $24 million in false negative ads against Ron DeSantis, Nikki Haley couldn’t buy herself the kill shot she so desperately wanted last night, and she will be out of this race after failing to win her home state on February 24.”

Haley’s own ad-makers watched the final months of the DeSantis campaign with bafflement. They thought his attack ads helped her reputation among moderates in Iowa, while appealing to Trump voters they viewed as unlikely to move anyway.

“I just don’t think that there is a single Republican who believes that Nikki is Hillary Clinton,” said Mark Harris, the lead strategist for SFA Fund Inc., a pro-Haley outside group. “Whereas people absolutely do believe that Ron is running a chaotic campaign.”

At nearly every point in the campaign, Haley had chosen to adopt a strategy diametrically opposed to what DeSantis was doing. Her team, at both SFA and the campaign, was led by a single crew of old friends and partners who operated as a whole, without leaks. Even the Iowa press spokespeople sought approval from Charleston headquarters before talking to national reporters.

While DeSantis leaned heavily on policy, Haley focused on big themes of generational change and political style. As the Florida governor’s allies announced a $100 million ground game, Haley ran on a shoestring, flying commercial for months, sometimes with just a single adviser. The DeSantis operation rented and wrapped three different buses — two for the super PAC and one for the campaign — while she had none.

But the charisma that drove her campaign was not without fault. It was a simple question that threw Haley off: What caused the Civil War? She rambled and did not mention slavery as a cause until the next day.

People who knew her in South Carolina said she had always been cognizant to appeal to voters who might be skeptical of an Indian American woman. Republicans and Democrats alike panned the answer. Even Trump mocked her, calling it “three paragraphs” of hokum, though he used another more colorful word.

She also struggled to broaden her coalition beyond moderate, affluent and college-educated voters. When former New Jersey governor Chris Christie left the race, he declined to endorse Haley and was overheard on a hot mic denigrating her. “She’s going to get smoked — you and I both know it. She’s not up to this,” Christie said, explaining why he was not backing her.

Still, she gained endorsements and attracted major donors who viewed her as the last hope against Trump as DeSantis struggled. By the final weeks of the campaign, Haley was spending nearly $1 million more a week than DeSantis was on Iowa television ads, while still flooding the New Hampshire airwaves where DeSantis had gone dark.

In a major blow to DeSantis, Americans for Prosperity Action, a political operation funded by the Koch donor network with field operations across the country, jumped in.

The endorsement of a hawkish candidate by a historically noninterventionist group took a moment to explain to many of AFP’s own activists in Iowa. But it instantly gave Haley a late presence on the ground there. The group knocked on 250,000 doors between Nov. 28 and the caucuses, it said, while activating its networks in the next nominating states headed into Super Tuesday.

“For us, it was who can win the nomination and who can beat Joe Biden?” said AFP state director Tyler Raygor. “Nikki Haley is the only candidate who can do both.”

On Monday night in Iowa, though, she still came in third, just behind DeSantis.

Trump, meanwhile, focused mostly on DeSantis, the opponent his campaign originally feared most.

At least eight advisers to the larger Trump effort had previously worked for the Florida governor, including Susie Wiles, his de facto chief of staff. Taken together, they had spent hundreds of hours with him.

At one point, Trump marveled to his aides that they disliked DeSantis even more than he did, according to a person who heard the comments.

Their early goal, multiple Trump advisers said, was to get into DeSantis’s head. They attacked him for wearing heeled boots because they believed he was insecure about his height. The pastry chef at Mar-a-Lago began making high-heeled chocolate cowboy boots to serve to guests for dessert, a lawmaker who visited Trump said.

They knew DeSantis could be a messy eater, prompting an ad attacking him for allegedly eating pudding with his fingers on a plane. They knew about how he liked to fly private, his love of playing luxurious golf courses, his enemies in Florida and his personality quirks — including that he often avoided interacting with others.

“If you didn’t know DeSantis, you’d think he was the conservative second coming in 2022,” one of these people said. “But those of us who really knew him, we knew better.”

Trump’s team knew what people who worked for DeSantis shared among themselves: The social media network once called Twitter could get the boss’s attention, in the same way Trump aides had used cable news appearances. The governor was known to follow certain reporters online, including local Florida bloggers.

“He was obsessed with Twitter and what the conservative influencers thought — he was always scrolling to see what those people were saying — so we tried to use them against him,” one Trump adviser said.

The campaign started social media battles with Roe, hoping to drive a wedge between him and DeSantis. Sympathetic provocateurs also got in the game, elevating obscure issues, challenging the governor from the right and insulting DeSantis aides.

“The whole macro strategy from the beginning was to bait them into fights that were not important,” said one of the agitators, Alex Bruesewitz, an online consultant who works with Trump’s son Don Jr. and spent his personal time taunting the DeSantis team. “They lower themselves to respond to a Twitter troll, and that is a terrible thing to do.”

DeSantis himself usually did not respond to the attacks, but people close to the former governor said he grew frustrated with them. Another adviser pushed back. “There’s not really that much you can go after him on when it comes to policy and results. … So, you know, they turned to the personal,” said one DeSantis adviser.

Others in the Florida governor’s orbit came to view the attacks as a growing burden, subconsciously wearing down voters, in the same way Trump nicknames like “Little Marco” and “Low Energy Jeb” stuck in 2016 for Marco Rubio and Jeb Bush.

“They were trying to run a policy campaign,” a former DeSantis staffer said of the operation. “And they’re assuming that normal voters are like policy wonks and technocrats. That’s not how normal voters think, and the Trump people got that very intuitively.”

Also key to weakening DeSantis was taking away his perceived stronghold of Florida, where he had come to dominate, with a 20-point reelection victory in 2022. Trump and his advisers took particular glee in having dinners, plane flights and other public events with Florida lawmakers.

Trump flew in several Tallahassee Republicans to walk with him at the Iowa State Fair. In total, Trump’s organizations spent more than $23 million attacking DeSantis, matching the more than $24 million spent by Haley, according to Federal Election Commission records.

Trump’s supporters on the ground in Iowa eagerly parroted the attacks on DeSantis. “They’re like baby birds; they eat whatever’s stuffed in their mouth,” said Matt Wells, an Iowa activist and county chair for DeSantis.

But the attacks on Trump’s opponents were just a part of his Iowa strategy this time. Following his dinnertime pleas, his team in the state focused on checking all the Iowa boxes he didn’t know about in 2016.

“Our experiment is whether we can get a lot of people to caucus for the first time,” one Trump adviser said. “They like the Trump merchandise.”

Like DeSantis, Trump planned for a record turnout of over 200,000 voters, not the 110,000 who ended up braving wind chill temperatures well below zero on Monday. Trump printed gaudy white hats with gold letters for top volunteers and created a Trump-loving cartoon character named Marlon to tell supporters how the process worked in a video. His team conducted more than 300 trainings. Top volunteers were also told that if they hit targets given by the campaign, they could attend a party in Milwaukee with Trump this summer.

Aides then convinced Trump to attend smaller “Commit to Caucus” rallies despite his initial preference for larger arena events, people close to him said. They explained that 700 or 800 people who would actually attend a caucus were more valuable than thousands who might not. “Commit to caucus,” Trump would repeat in private, in a sarcastic tone, they said.

In a conference room at the hotel in recent days, Trump called 20 different caucus captains, who erupted with surprise and glee to learn that Trump was on the phone.

As a blizzard descended on Iowa, Trump campaign aides asked members of the “Farmers for Trump” coalition to use their tractors to clear rural gravel roads so their voters could get to the polls.

By the final weekend, Trump had amped up his pleas, telling his supporters at an event Sunday in Indianola that nothing should stop them from showing up Monday night.

It was a smaller room than Trump usually populates, but the crowd flowed into an overflow space. Denise Nelson, a volunteer handing out paraphernalia in the hallway, said Trump had more volunteers than in 2016 when she first started supporting him, drawn by his defiance and cries of martyrdom.

“It helps him when they say fabricated and fake things about him,” she said. “So to those people, I say thank you.”

As he flew back to New York in the wee hours of Tuesday, Trump blared music videos on a big screen on the plane — beginning with “November Rain” by Guns N’ Roses and then listening to James Brown, Lionel Richie and Sinéad O’Connor, among other artists.

Hours later, he was back in court for the penalty phase of a civil defamation trial, following a jury verdict that found he sexually attacked a woman in a department store in the 1990s.

Marianne LeVine and Dylan Wells contributed to this report.