Inside DeSantis’ Plan to Outwork Trump in Iowa

Florida Gov. Ron DeSantis views Iowa as such a make-or-break state for his presidential bid that he’s considering a plan to campaign across all 99 of its counties, insiders familiar with his thinking tell The Messenger.

As the first presidential contest, the Iowa caucuses play a pivotal – and unpredictable – role in presidential nominations, but they take on outsized importance in 2024. Former President Donald Trump is ahead in the polls with a double-digit lead over DeSantis, who in turn is well ahead of a handful of third-tier candidates.

So if DeSantis loses Iowa, it could give Trump an aura of inevitability and a sense of momentum that leads to a cascade of victories that make him the de facto nominee.

If DeSantis prevails, however, it could set the stage for a two-man race heading into New Hampshire’s primary, advisers have privately acknowledged to allies and donors who shared the thinking of the Trump and DeSantis campaigns with The Messenger. 

DeSantis’s team is almost as heavily focused on New Hampshire – which he visits Friday – and his advisers have privately acknowledged he would need to win this second state just to stay alive. Both campaigns agree this scenario could lead to a prolonged battle across more than a dozen states leading up to a March 19 primary showdown in the home state of both men, Florida.

But it all hinges on DeSantis winning Iowa, or coming so close it looks like a Pyrrhic victory for a damaged Trump.

DeSantis’ Iowa playbook 

A political committee backing DeSantis called “Never Back Down" already has an operating budget of about $100 million and is embarking on a hiring binge in the first 19 states, according to a senior adviser who discussed the plans on condition of anonymity with The Messenger. That includes an Iowa carveout of about $10 million for field operations and up to 80 full and part-time staff, two sources briefed on the plans told The Messenger.

“DeSantis is in it to win it,” said Bob Vander Plaats, an Iowa evangelical leader who is neutral in the race so far. 

Vander Plaats dined with DeSantis and his wife, Casey DeSantis, on May 8 in Tallahassee at the Governor’s Mansion. And he got the impression that DeSantis would campaign as hard as Iowa’s iconic Republican Senator, Chuck Grassley, visiting every county.

“It will not surprise me if he does the ‘Full Grassley.’ It won’t surprise me if he does every Pizza Ranch stop in Iowa,” Vander Plaats told The Messenger. 

In an example of DeSantis’s Iowa work ethic, Vander Plaats pointed out that the governor was in the state Saturday at two events across the state, but he added a third stop in Des Moines after Trump canceled a nearby rally in the city due to the threat of tornadoes. That left Trump grounded at home in Palm Beach, Florida, while DeSantis had Iowa to himself. 

“What you saw Saturday was the contrast he’s going to show in Iowa,” a DeSantis confidant who recently spoke to the governor told The Messenger on condition of anonymity to discuss the campaign’s thinking. “Ron is basically gonna move to Iowa. He’s a 44-year-old Navy vet and former [college Division 1] baseball player. He’s a machine. Trump is 76. And it shows. Iowans will see it with their own eyes when Ron is doing the ‘Full Grassley’ while Trump is playing golf like some retiree at a resort back home.”

But, the confidant said, DeSantis won’t actively mention Trump’s age during the primary, in part because the GOP electorate tends to be older than the average American citizen.

Trump’s theory of the case

Trump’s campaign — which is taking the DeSantis threat in Iowa seriously — has focused on Iowa for months after its early launch in November.

The Trump campaign has begun contacting more than 40,000 Trump voters it identified by combing through precinct data, political contributions and rally-goer information it collects from cell phones that attendees furnish the campaign to go to the events, a senior Trump adviser told The Messenger on condition of anonymity to discuss internal efforts.

About 200,000 people could turn out for the Iowa caucuses, meaning the 40,000 people the Trump campaign has already identified could make up 20 percent of his voters prepared to caucus already. With a crowded field, that would get him close to a winning margin. In 2016, during the multi-candidate Republican primary, Texas Sen. Ted Cruz won the caucuses with 28 percent of the vote when more than 180,000 people turned out.

As in 2016, this cycle’s Republican primary field could be packed with candidates, but this time there’s widespread agreement in GOP circles that more candidates gives Trump an advantage, preventing any other single candidate from consolidating enough support to compete with Trump’s unshakeable base, which makes up at least a quarter of the electorate.

If non-Trump candidates divide the non-Trump vote, the looming campaigns of South Carolina Sen. Tim Scott and Vice President Mike Pence become more threatening to DeSantis, especially in the early states.

“DeSantis can campaign all he wants in Iowa, and it’s not going to change the facts that we’re way ahead and Ron’s got multiple problems with Scott or Vivek [Ramaswamy],” a Trump senior adviser said. “Trump heard all this stuff about how he was going to get outworked in 2016 in Iowa and he damn-near won even though the campaign was a total shitshow then. It ain’t now. We’re ahead in the polls and ahead on the ground. And Ron knows it. But we know it, too.”

A different Trump campaign

Indeed, in 2016, the Trump campaign was widely derided as such a disorganized mess that 10,000 pledge cards for Trump were found in its Des Moines office, the data unused and the voters never contacted. 

Never Back Down and the Trump-supporting political committee MAGA Inc., have already spent millions on ads and mailers, and DeSantis’s team boasts it has more endorsements from Republican leaders in Iowa and New Hampshire so far.

DeSantis’s early state endorsements, rolled out in recent days, took on added significance after the buzz over his potential candidacy died amid Trump’s constant criticisms of personality, questions about his retail politics skills and doubts about how he answered questions about the war in Ukraine and how to Trump’s indictment on business fraud charges in New York City in March.

Trump then surged ahead in polling over DeSantis, though DeSantis’s favorability ratings remained almost as strong or stronger than Trump’s in many states, according to presentations that DeSantis pollster Ryan Tyson made to top donors who flew to Tallahassee earlier this month for briefings with the governor and top staffers.

Barack DeSantis?

One donor who spoke on condition of anonymity to describe the meetings said the briefings were persuasive but it was clear that Trump was in a commanding position.

“The takeaway I got is we have to win Iowa and New Hampshire to stay alive, but no one has done that before [who’s not an incumbent],” the donor said. Others who have discussed the DeSantis campaign’s potential path said his team sees Trump as particularly strong in Nevada and South Carolina, the last two early states before the March run of primaries.

No Republican has secured the nomination without winning Iowa or New Hampshire since 1976, when the GOP followed Democrats’ lead and first made the Iowa caucuses the first contest. And since then, Iowa and New Hampshire have never picked the same nominee when a non-incumbent runs in Republican contests. 

“This year could be different if DeSantis doesn’t stop Trump,” said Patrick Hynes, a top Republican consultant in New Hampshire who’s not aligned with any candidates.

“If Trump wins Iowa he’ll enter New Hampshire with a head of steam almost impossible to overcome, despite the history of New Hampshire going a different direction, so barring something utterly unforeseen he’ll probably be the nominee,” Hynes said.

“If DeSantis wins in Iowa – or comes unexpectedly close that it looks almost like win -- then it’s on,” Hynes said. “It’s going to be a brutal fight in New Hampshire because Trump is strong here.”

Jeanita McNulty, who chairs the Scott County GOP in Iowa, said the dynamic in the 2024 Republican race has echoes with the 2008 Democratic caucus, when Sen. Hillary Clinton was the favorite to win and Sen. Barack Obama was seen as a longshot, who shocked the political class by winning.

“Obama has Iowa to thank for making him president. It really skyrocketed him,” she said, noting that a Clinton win would have snuffed out his candidacy.

If Trump is in the Clinton position today, can DeSantis pull an Obama?

“It’s a strong possibility,” she said. “But it’s anybody’s game. It’s still early.”