Organizing is key to the Iowa Caucuses. Who has the ground game to take on Trump?

Florida Gov. Ron DeSantis is quadrupling down on his all-in Iowa strategy by shifting a third of his campaign staff into the state over the coming weeks.

Former U.N. Ambassador Nikki Haley is growing her campaign in the state — adding experienced Iowa hands to her team and opening a Clive headquarters.

And former president Donald Trump is dramatically ramping up his campaign calendar. Five public rallies have been scheduled during the first three weeks of October as his operation seeks to ensure its supporters show up on caucus night.

The focus on Iowa's ground game comes as the caucus cycle enters its final months — the make-or-break time when past winners have tapped into their organizational strength to surge ahead of their competitors and claim victory in the crucial first-in-the-nation contest.

So far, Trump has maintained a steady and robust polling lead over his Republican primary opponents. And his Iowa operation is far more sophisticated than it was when he placed second in the 2016 Iowa caucuses.

But candidates like DeSantis and Haley are investing in their ground games to try to make up the difference and lock in supporters in these critical final months.

“They need to have enough staff and structure, which includes volunteers, to be able to really capture the support that they're starting to get,” said David Kochel, a Republican political operative who has worked for multiple Iowa caucus campaigns. “You need to have enough people to help you turn that support into actual identified caucusgoers. And then you've got to organize it by precinct.

“It's labor intensive. It's a lot of that blocking and tackling that can't be done by a couple of national political staffers. You've got to have some people on the ground.”

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In some cases, candidate have been building relationships in the state for years. But many have been slower to build out their physical infrastructure with staff and offices than in past cycles, some observers say.

As candidates look to grow their Iowa footprints into the fall and winter, it raises the question: Is it already too late to create a winning ground game — particularly when Trump leads in polling by such large margins?

“That infrastructure can't be built overnight,” said Drew Klein, a Republican operative and the Iowa state director for Americans for Prosperity. “And so I think not having it right now does not completely eliminate you, but you don't have a whole lot of time to start building.”

Five of the past six winners of the Iowa Caucuses didn’t lead a Des Moines Register Iowa Poll until November or later (Barack Obama, Mike Huckabee, Ted Cruz and Pete Buttigieg) or never led one (Rick Santorum). The only exception was Hillary Clinton, who consistently led the Iowa Poll throughout 2015 and early 2016, but with a shrinking margin. She ultimately won the caucuses by just a fraction of a percentage point over Bernie Sanders.

It's a fact that helps fuel the belief among candidates and operatives that the door is still open to major shifts in the 2024 race.

“It feels like the race has been going on for a long time,” Klein said. “But we know, historically, the caucuses are going to break and kind of take their final form more in November and December. And so I think what we've seen so far is really just the laying of the foundation.

“The question is who's actually going to build on that foundation for the next couple of months?”

Ron DeSantis leads in scale of Iowa caucus infrastructure

Between his campaign and super PAC, DeSantis leads the field in terms of the sheer scale of his Iowa operation.

His campaign is expected to have about two dozen staffers on the ground following a shift in resources from his Tallahassee, Florida, headquarters into Iowa.

And his Never Back Down super PAC has 22 full-time Iowa staffers spread across five offices in West Des Moines, Cedar Rapids, Council Bluffs, Davenport and Sioux City.

Never Back Down started organizing early, building out its Iowa operation in March and launching a five-day canvasser training program at a Des Moines area office nicknamed “Fort Benning” after an army base originally named for Confederate Gen. Henry L. Benning and renamed in 2023.

Never Back Down canvassers began knocking on doors in April and have since tallied more than 465,000 doors, the group said.

“We anticipate there's going to be around 217,000 Republican caucusgoers on Jan. 15. So we have knocked on the door of every single one of those at least once,” Never Back Down Chief Operating Officer Kristin Davison said. “We will probably knock on them a total of five times throughout the state.”

Never Back Down has also taken over as the driving force behind DeSantis’ Iowa visits, organizing bus tours and inviting the governor as a “special guest.” DeSantis has committed to visiting each of Iowa’s 99 counties as he courts Iowa votes, and his campaign said he is nearly two-thirds of the way there.

But so far, the massive investment in both time and resources has not resulted in a bump in the polls. A Real Clear Politics rolling average of Iowa polling puts DeSantis at 16% — about 33 percentage points behind Trump and only about 7 points ahead of Haley, his next-closest competitor.

“The great news is, we're certainly not where we want to end up, but we are exactly where I had hoped we would be at this point,” said DeSantis' campaign manager, David Polyansky. “Meaning we've got, by far, the only meaningful and significant caucus operation in the state.”

The PAC has assembled a list of 99 county captains, plus a coalition of Iowa parent activists, and it has collected more than 18,000 commit-to-caucus cards. The campaign has launched endorsements from 40 state legislators, including some legislative leaders, and announced coalitions of faith leaders and the “Mamas for DeSantis group.”

Kochel said campaigns should have identified leaders in all or most of the state's 99 counties by now, and they should be able to identify volunteer leaders in a significant chunk of the state's nearly 1,700 precinct locations to help supporters navigate the process on caucus night.

"A lot of these campaigns will have kind of a national volunteer network of people working phones for them," he said. "Some will be able to sustain a lot of that in-state with volunteers they recruit or with super PAC support. But it needs to be happening all through this fall. It's not late yet, but it's definitely high season for recruiting people into the organization."

Former New Jersey Gov. Chris Christie, who is focusing on New Hampshire, has hired no staff, opened no offices, knocked on no doors, aired no television ads and made no campaign appearances in Iowa.

Political newcomer Vivek Ramaswamy spoke aggressively at the start of his campaign about building a grassroots organization, but his staff declined to speak to the Des Moines Register for this story.

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Nikki Haley builds out ground game more slowly in Iowa Caucus 'marathon'

Haley has been slower to build out an Iowa field operation than DeSantis and some others. A Haley campaign spokesperson said the focus has been on growing relationships in the state, respecting donors’ dollars and building out an operation at the right time.

“We're in a marathon, not a sprint,” the spokesperson said. “And we have made no secret about the fact that we are a leaner machine but also a meaner one. So our efforts on the ground are growing with us.”

But Haley announced on Monday she is expanding her Iowa footprint following a pair of well-received debate performances that have prompted fresh interest among some Iowa Republicans as well as national donors who see her, rather than DeSantis, as the best candidate to take on Trump.

The Haley campaign is opening its first headquarters in Clive, adding two staffers with Iowa political experience and hiring others as it seeks to capitalize on the momentum.

New on the team are Hooff Cooksey, who managed Republican Gov. Kim Reynolds’ winning 2018 race, and Troy Bishop, who was U.S. Sen. Chuck Grassley’s 2022 field director. They join a core group of leaders that includes state Sen. Chris Cournoyer and state Reps. Austin Harris and Shannon Latham.

Haley has also launched her Women for Nikki coalition in Des Moines. The Iowa coalition is co-chaired by Emily Sukup Schmitt and Rachel Gellenfeld.

Her allied Super PAC, SFA Fund, has run about $7 million worth of TV ads supporting her in Iowa.

Donald Trump campaign: ‘We will win Iowa’

Hundreds of people wearing “Make America Great Again” apparel waited in a long line that snaked through a chilly Waterloo parking lot on a recent Saturday morning as they waited hours to see Trump take the stage.

The challenge for Trump’s campaign is not in getting Iowans to attend his events and learn his positions. It will be in ensuring they know how and when to caucus and will commit to turning up to support him in January.

Volunteers stood with clipboards, taking in attendees’ information as they signed “commit to caucus” pledge cards. Campaign adviser and state Rep. Bobby Kaufmann promised the crowd that a caucus is no more intimidating than voting.

And Trump himself has been urging his event attendees to turn up on Caucus Day.

“So it's 7 p.m. on Monday, Jan. 15,” Trump told the Waterloo crowd soberly. “And we are asking you to bring five or six or seven or 10 people with you — as many as you can. Get them loaded up. And we want to have a big beautiful send-off.”

Alex Latcham, the campaign’s early states director, said the Iowa campaign has secured caucus pledge cards from more than 33,000 Iowans who are entered into a database within 48 hours and contacted again by the campaign.

The campaign has identified 1,600 unique in-state volunteers who have turned up to support the campaign, as well as 200 county chairs representing all 99 counties, he said.

And the campaign has recruited 1,100 caucus precinct captains who will represent Trump at about 850 of the state’s nearly 1,700 precinct locations, Latcham said. So far, the campaign has prioritized the larger precincts where they know significant numbers of Trump supporters are located, but they plan to have every precinct covered by December.

Unlike DeSantis, Trump’s efforts are mostly run through his campaign, which has more than a dozen staffers and at least two campaign offices, in Des Moines and Cedar Rapids. His super PAC, MAGA Inc., has been airing ads in Iowa but declined to comment.

Although the campaign is trying to persuade people to support Trump, Latcham said a major focus is on keeping existing supporters engaged and ensuring they turn up to caucus.

At the Waterloo event, Kaufmann asked attendees to raise their hands if they’d never participated in a caucus before. About a third indicated that 2024 would be their first time — presenting both an opportunity and a challenge for the campaign.

“People know who President Donald Trump is,” Latcham said. “They know what he stands for. And it's up to our staff to go out and just constantly remind voters of his accomplishments and organize them and make sure they are educated about the caucus process, where they need to go, when they go, etcetera.”

Trump campaign officials dismiss their opponents’ hopes for a late-breaking surge in the polls, regardless of their field operations. Trump's 30-point polling lead is historically large, they say, and his challengers have so far failed to eat into it in any meaningful way.

“We will win Iowa,” Latcham said. “And, quite frankly, if you can't organize and win in a state like Iowa that's tailor-made for candidates with its low advertising costs and basically no barriers to participate — we don't have a filing fee in Iowa, there's no signature requirements — then it does beg the question of how can candidates feasibly make a claim to be competitive elsewhere?”

Ron DeSantis, Mike Pence, Tim Scott lean on their super PACs for Iowa field organizing

In a state where organizing is key, candidates are outsourcing more of that work to super PACs than ever before, experts say.

DeSantis is the prime example, with his Never Back Down PAC organizing and hosting his statewide bus tour. The move allows DeSantis to lean on his well-funded PAC while freeing up his campaign, which has faced cash flow problems, to focus on other things.

But he's not alone. U.S. Sen. Tim Scott and former Vice President Mike Pence have also begun delegating things that previously had been staples of a presidential campaign, such as door-knocking, to their associated super PACs.

“The way that campaigns are largely shifting costs off to these super PACs for events and grassroots and a lot of those ground game components — I mean, it has flipped 180 degrees, it seems, from 2016,” Klein said. “They are the ones leading in that space now, and the campaign is definitely kind of the lagging indicator on where the super PACs are spending money.”

Unlike campaigns, super PACs can raise and spend unlimited amounts of money supporting a candidate, so long as they don’t directly coordinate with the candidate or the candidate’s campaign.

That can lead to situations where the PAC and the campaign are signaling their intentions to each other through the media or other ways. DeSantis was embarrassed earlier this year when a firm associated with his super PAC posted a memo on its website, outlining to the candidate and his campaign how DeSantis could secure a debate victory.

The Federal Election Commission has said PACs can host events for candidates, but it has not yet weighed in on whether they can run a field operation for a campaign, said Shanna Ports, senior legal counsel for campaign finance with the Campaign Legal Center.

But Ports said the FEC has been weak on enforcing its anti-coordination rules, perhaps emboldening candidates and outside groups to push the boundaries of what PACs can legally do.

"I think certainly the more a super PAC's activities begin to mirror what campaigns traditionally do, the more it raises the question of whether any of those sort of prohibited contacts are going on behind the scenes," she said.

Pence’s campaign employs three Iowa-based staffers, an adviser said, but much of the ground game — including grassroots door-knocking and pushing people to attend events — is being handled by the super PAC.

His campaign manager, Stephen DeMaura, was an early adopter of the super PAC strategy when he was part of Carly Fiorina’s 2016 presidential campaign. Fiorina’s PAC drew attention in Iowa when it began hosting events for her ahead of the 2016 caucuses.

Today, Pence’s Committed to America PAC has about 40 people who are hired through a subcontractor to staff its voter contact efforts, PAC spokesperson Mike Ricci said. The PAC says it has knocked on more than 530,000 doors in Iowa, and it has collected data from nearly 50,000 likely caucusgoers. It’s also aired about $400,000 worth of TV ads.

"We've been so aggressively focused on door-to-door voter contact because it is the most effective and cost-efficient way to identify persuadable caucusgoers for (get out the vote) efforts," Ricci said.

Scott’s campaign declined to answer questions about its Iowa operation. But his associated super PAC, TIM PAC, has “almost a half-dozen full-time staff” in Iowa and nearly 50 canvassers, who are a mixture of paid and unpaid workers, a PAC official said.

The PAC said it had knocked on more than 300,000 doors and had spent more than $5 million on digital and TV ads as of Sept. 22.

Polyansky, who worked on DeSantis’ Never Back Down PAC before transitioning to serve as his campaign manager, described Never Back Down as the “offensive line” for the campaign.

But he said the campaign will likely take on a larger role in Iowa in the final stretch before the Iowa Caucuses.

“Our hope is that they continue, on the other side, to show up at our events, to sign people up, to motivate them and get that caucus turnout operation going,” he said.

Des Moines Register reporters Katie Akin, Stephen Gruber-Miller, William Morris, Phillip Sitter and Amanda Tugade contributed to this article.

Brianne Pfannenstiel is the chief politics reporter for the Register. Reach her at bpfann@dmreg.com or 515-284-8244. Follow her on Twitter at @brianneDMR.

This article originally appeared on Des Moines Register: Trump, DeSantis, Haley: Who has the strongest Iowa Caucus ground game?