DeSantis, all-in on Iowa, finishes 99-county tour where he started: Far behind Trump in a critical state

Newton, Iowa (CNN) — Florida Gov. Ron DeSantis completed his tour of Iowa’s 99 counties on Saturday, a milestone he pursued with dogmatic zeal as his White House aspirations grew closely tied to his performance in the Republican Party’s first presidential nominating contest.

DeSantis marked the occasion with a rally in Jasper County, just east of Des Moines at a venue called the Thunderdome – a fitting host for a candidate in a fight for political survival.

“I don’t think doing the 99 counties is just about the caucus. … The fact that I’m willing to do this, that should show you that I consider myself a servant, not a ruler. And that’s how people that get elected should consider themselves,” he said at the rally Saturday.

With just over six weeks until the January 15 Iowa caucuses, DeSantis remains well behind the party front-runner, former President Donald Trump, and is running out of time to catch a spark. Meanwhile, the surging campaign of former South Carolina Gov. Nikki Haley has turned its attention to the Hawkeye State, further complicating DeSantis’ path to a victory in a place he is all-in on winning.

Now, DeSantis’ presidential bid hinges on how Iowa Republicans, who have long prized retail campaigning, respond to the early and persistent connections he has made while logging thousands of miles through the state’s cornfields and wind farms.

“I think you have to do that to win Iowa,” DeSantis said Thursday about visiting the state’s 99 counties. “I think that’s what voters want to see. I think they want to be able to meet you, they want to be able to ask your questions.”

On the road to appearing in every Iowa county – a feat known as “the full Grassley,” named after the state’s well-traveled senior senator, Chuck Grassley – DeSantis has regularly appeared in parts of the state Trump is unlikely to visit. He has shaken countless hands and answered questions from potential supporters in dozens of small shops, bars, manufacturing plants and similar venues, from the Missouri River to the west and Mississippi River to the east as well as the borders of Minnesota to the north and Missouri to the south.

It’s an undertaking DeSantis first embarked on this summer to stabilize a campaign that was struggling to break out and was dealing with cost overruns caused in part by an overly ambitious national push out of the gate. Doubling down on Iowa with stops in all corners of the state became a guiding star for the revamped effort behind DeSantis, which also involved moving most of his staff from Tallahassee, Florida, to Des Moines, replacing his campaign manager and adding David Polyansky, a seasoned Iowa operative who previously worked for Never Back Down, a super PAC supporting the Florida governor.

He got 99 counties but doesn’t have Iowa won

While he has struggled to find his footing in the art of retail politics, completing “the full Grassley” is the latest accomplishment by a candidate who, on paper, appears to have checked off everything a presidential contender is supposed to do to win the Iowa caucuses.

Never Back Down has spent more than any other entity on advertising in Iowa and is building out a ground operation it insists is “historic” in its size and early deployment. DeSantis also earned the endorsement of the state’s popular Republican governor, Kim Reynolds, and Bob Vander Plaats, one of Iowa’s most influential faith leaders.

But in the months since DeSantis first set out to visit every county, polls show Trump’s lead in Iowa has only grown. DeSantis’ attempts to engineer momentum by blanketing the state have yet to materialize into a groundswell of new support. Haley’s competing campaign recently received a boost when she was officially backed by Americans for Prosperity Action, the network associated with billionaire Charles Koch that has vowed to spend tens of millions of dollars to ensure Trump doesn’t win the nomination.

Further complicating his efforts in Iowa is the tension between his political operation and Never Back Down. DeSantis and his wife, Casey, a top adviser to him, have been unimpressed with Never Back Down’s advertisements in Iowa, particularly those focused on Haley. A new pro-DeSantis super PAC has emerged in recent weeks, Fight Right, led by several longtime advisers with a goal of airing ads more critical of Haley as she seeks to make inroads in the state.

Amid the fallout, Never Back Down’s chief executive, Chris Jankowski, stepped down, saying the current environment there made it “untenable for me to deliver on the shared goal” of electing DeSantis to the presidency. Adam Laxalt, DeSantis’ former roommate and one of his closest friend in politics, departed the super PAC this week as well after serving as its board chairman.

DeSantis, who regularly reminds Iowans how much time he has spent with them, has said he believes the work he has put in will pay off in the coming weeks as caucus goers begin to pay attention to the race in earnest. The hope is that the Iowa caucuses, which have a history of breaking late and producing unexpected results, will once again produce a surprise.

Internally, however, advisers recognize DeSantis has few outs if the outlook in Iowa doesn’t improve soon.

“If it doesn’t, it was a major miscalculation and then I don’t know what will happen,” said one DeSantis adviser, who asked not to be named to speak openly about the Republican’s campaign. “We need a strong showing in Iowa in order to build momentum and show viability going into early primary states. We have enough money to do that.”

A Republican fundraiser close to DeSantis’ political operation added: “There’s gotta be movement in the next month or there’s serious trouble for him.”

A mixed track record for candidates who go full Grassley

Visiting all 99 counties has become a perennial fixture of the presidential election cycle for many Republican candidates as they try to replicate the annual tour that Grassley, 90, has done for decades.

It’s a fairly inexpensive way for candidates to reach the more passionate Republicans likely to trek to a voting site in the dead of winter, given that a caucus is simply a neighborhood meeting held in more than 1,000 precincts across the state.

“The expectation among voters is that they get a chance to see and talk to candidates up close, and kind of make that personal connection,” said Christopher Larimer, a University of Northern Iowa political science professor. “So going to 99 counties helps develop that relationship and it shows to voters that the candidates are willing to make the effort to go to all parts of the state to develop those relationships.”

Former Iowa Gov. Terry Branstad and Grassley started the tradition of visiting all the counties in Iowa – which is one of the top 10 states with the most counties – in the 1980s, according to Larimer. Iowans became used to seeing their politicians around their state, generating expectations that presidential candidates would do the same, Larimer said.

The 99-county tour appeared to work for Republican Sen. Ted Cruz in the 2016 cycle as he placed first in the Iowa GOP caucuses ahead of Trump, who flew into the state for large rallies rather than engaging in retail politics. The Texas senator was cramming in stops to Iowa’s less populated counties in the last week before the caucuses and didn’t hit 99 until the day of.

Hitting the 99th county in early December provides more flexibility for DeSantis’ calendar going forward, the campaign believes. Nor does it wed him to only campaign in Iowa down the stretch. DeSantis, for example, spent Friday in South Carolina.

“The beauty of wrapping up the 99 counties this early is that while every single caucus-goer in the state will already have had the chance to meet Ron DeSantis, we will no longer have the map dictate where we go, but now we can allow our targeting dictate where we go,” Polyansky told CNN.

The DeSantis campaign shared a statement Friday from the namesake of the 99-county feat complimenting the governor’s efforts.

“I have found it is the best way to show Iowans everyone is important to hear from and no one is forgotten by their senator,” Grassley said.

Steve Scheffler, a Republican National Committee member from Iowa, said courting Iowans takes more than appearing once in their part of the state and DeSantis can’t be seen as merely visiting to cross off another county.

“I’m not downplaying it. It’s good,” Scheffler said. “But you know, sometimes, especially if you’re not the favorite in the race, going to those counties umpteen times until you’re blue in the face probably is not a bad idea.”

Other 2024 contenders have downplayed the impact of DeSantis reaching the milestone. Trump’s campaign this week needled DeSantis by pointing out that Ryan Brinkley, a little-known Dallas pastor also running for the GOP nomination, had already visited all 99 counties but his support was virtually non-existent.

Entrepreneur Vivek Ramaswamy predicted he will have completed the “full Grassley two times and then some” but it wasn’t something he intended to celebrate.

“I’m not a ‘check the box’ guy,” he told reporters at his new headquarters in Iowa. “We’re organically going to where people want to hear from us.”

A visit to every corner of the state does not necessarily translate to a win in Iowa, as the success rate for a candidate who completes the so-called full Grassley has shown.

Former Pennsylvania Sen. Rick Santorum finished the 99-county tour in 2012, which may have helped him notch a win over well-funded Mitt Romney’s campaign. But Michele Bachmann did the same and finished in sixth place. Santorum was out in Iowa early and often while Bachmann hustled to finish her 99-county tour in 10 days.

In 2016, Santorum and former Arkansas Gov. Mike Huckabee both completed the full Grassley, hoping to repeat their 2012 and 2008 Iowa caucuses wins, respectively. But Huckabee ended his presidential bid the night of the caucuses after a poor showing of less than 2%. Santorum fared even worse in the caucuses than Huckabee.

But Cruz, Huckabee and Santorum did not turn their success in the Iowa caucuses into a presidential nomination. The DeSantis campaign is banking that he is uniquely positioned – thanks to solid fundraising and campaign work in early primary states – to turn a victory in Iowa into a springboard toward the nomination.

History, however, says that’s a risky proposition and signs of trouble are already appearing in New Hampshire and South Carolina, where Haley appears ahead of DeSantis.

“Look, either the full Grassley and all the money the super PAC has put into the ground game, the millions we’re putting into advertising there, and all the personal contact he’s making, either it works or it doesn’t,” the DeSantis adviser said. “But we won’t know until caucus day.”

The last time a Southern governor won the Iowa caucuses and went on to become the Republican nominee was 2000, when George W. Bush waged a far more modest campaign in Iowa. He did not complete a full tour of Iowa’s 99 counties – but he made it to the White House.

This story has been updated with additional developments.

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CNN’s Kit Maher contributed to this story.