Boom or Bust: Monday’s Iowa caucuses the biggest test of DeSantis’ political career

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Eight months after Gov. Ron DeSantis officially entered the race for the presidency, a state 1,000 miles from home could determine if it ends soon or has new life.

It all comes down to Iowa.

The state will serve as the first tangible test of whether DeSantis’ influence, clout and popularity in Florida can extend outside its borders, making Monday’s caucuses unquestionably the most important moment to date in his political career.

Iowans who shiver their way to Monday night’s subzero caucuses at places like recreation centers and elementary schools will decide whether DeSantis’ governing, which has left a deep imprint on Florida, is enough to earn their support.

DeSantis has barnstormed the Hawkeye state at a breakneck pace, packing in five or more events per day as he hammers his pitch in coffee shops, sports bars and Elks lodges. At times, his voice has grown hoarse. His campaign’s tone in recent TV ads has turned negative, taking aim at former United Nations Ambassador Nikki Haley, the biggest threat to his hold on No. 2 in the state.

It wasn’t supposed to be this way.

DeSantis started 2023 with soaring expectations, as a governor whose landslide reelection posed a direct contrast to Republicans’ disappointing midterm results that many blamed on former President Donald Trump. Even after his glitchy Twitter campaign launch, the DeSantis team’s confidence seemed boundless.

After spending lavishly, however, his campaign was forced to lay off more than a third of its massive staff. The main pro-DeSantis super PAC, which initially handled a huge amount of his political operation, was so optimistic that it spent thousands in June contacting voters by phone in Oklahoma, a state whose primary isn’t until March.

Now, his team and his donors are hoping that the poll numbers are wrong.

The latest Iowa surveys show DeSantis roughly 30 points behind Trump. Haley is within a few-point striking distance of second place.

DeSantis has said that he will defy the odds to win Iowa, though many Republican operatives say a strong second-place showing that separates him from the other non-Trump candidates could be enough to keep his campaign afloat.

Anything less?

“If Iowa is a bust and he doesn’t do well, I think it’s doom for the campaign,” said Jim Merrill, a Republican strategist in New Hampshire.

READ MORE: How Iowa could spell the end for Ron DeSantis

All-in on Iowa

DeSantis has spent far more time and money in Iowa than in any other state — including New Hampshire, which has its primary on Jan. 23. He’s long been outpolled in the Granite State by not only Haley but former New Jersey Gov. Chris Christie, who dropped out of the race this week.

The two main super PACs supporting DeSantis have spent nearly 15 times more money on Iowa than on all other states combined, according to a Tampa Bay Times analysis of campaign finances. The more than $43 million they’ve spent in Iowa dwarfs the $2 million they’ve spent so far in South Carolina and about $850,000 they’ve spent in New Hampshire.

DeSantis started making appearances in Iowa before declaring to run, first visiting in March to promote his new memoir. His official campaign kickoff was held in Clive, just outside of Des Moines, in late May. Since then, he’s spent at least 50 days campaigning in each of the state’s 99 counties.

DeSantis rode bumper cars at the Iowa State Fair and played catch with son Mason on the “Field of Dreams” baseball diamond in Dyersville. He floated the idea of moving part of the Department of Agriculture to Iowa. He won coveted endorsements from popular Gov. Kim Reynolds, influential pastor Bob Vander Plaats and dozens more legislators, sheriffs and local officials.

“You’ve basically telegraphed to the world your theory of the case is, ‘We’re going to do well in Iowa; we’ve put a lot of time and money there,’” Merrill said. “If voters say, ‘That’s nice, but we’re going to make you a distant second,’ then it’s very hard to come to New Hampshire where he hasn’t put the time in, or South Carolina, Haley’s home state, to turn things around.”

While DeSantis’ campaign has previously claimed that it’s a “two-man race” between him and Trump, its spending shows it is well aware of the threat Haley poses.

From October through December, after Haley started surging in the polls, the two main super PACs supporting DeSantis poured more than $12.2 million into anti-Haley mailers, texts, ads and graphics in Iowa. That’s more than they spent on pro-DeSantis messaging in that period, according to federal paperwork. Prior to October, the groups had barely touched Haley in their publicly disclosed expenditures and spent just a few hundred thousand dollars on anti-Trump messaging.

DeSantis has responded to questions about polling struggles by telling Iowans that polls don’t matter; votes do.

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“Nobody’s leading until you guys get to vote,” he said during a Jan. 5 CNN town hall in Des Moines. “You guys get to make the decision. Don’t let the media or the pundits make the decision.”

The vote could be closer than expected if turnout is low due to bad weather. After a week that has seen nearly a foot of snow in places, below-zero temperatures are expected Monday in Des Moines. Trump, Haley and entrepreneur Vivek Ramaswamy have already altered or canceled events due to the winter storm.

DeSantis supporter Barbara Hovland, president of the Northern Iowa Republican Women, believes public polls aren’t capturing what she’s hearing and seeing at recent “coffee caucuses” she organizes around Mason City. She’s met a handful of Trump supporters who have changed their minds after hearing both candidates speak — the former president at enormous, impersonal rallies, Florida’s governor at more intimate town halls.

“When you look at the independents across the state of Iowa, they can decide the race if they get out and vote,” she said. “That’s a very strong base. Are they going to caucus, or are they going to change their registration to Republican that night, or have they already done it in preparation to vote for somebody like him? I think you’re going to see Ron DeSantis get some independents as well.”

DeSantis has also worked hard to court Iowa’s evangelical vote, touting the endorsement of more than 100 Iowa pastors and faith leaders.

Anytime a pastor decides to endorse a candidate, it can make a real difference in Iowa, said Chad Connelly, president of a group called Faith Wins that connects candidates with clergy and has held events with DeSantis.

“I think it has a lot of sway,” Connelly said.

A crumbling campaign

While DeSantis has had to fend off negative headlines about his poll numbers, an explosion of internal drama just before the end of 2023 marked a self-inflicted wound that couldn’t have come at a worse time.

The driving force behind DeSantis’ strategy was Never Back Down, a Super PAC created nearly two months before he officially entered the race. The group was so integral to DeSantis’ efforts that it drew the attention of watchdog organizations that argued it was closely coordinating with DeSantis’ official campaign, which would be a violation of federal election law.

But between approximately Thanksgiving and Christmas, Never Back Down’s chief executive Chris Jankowski, chairperson Adam Laxalt and senior adviser Jeff Roe resigned; Jankowski’s replacement, Kristin Davison, was fired.

By mid-December, the constant turmoil surrounding the Never Back Down super PAC culminated in the group losing its responsibility to shell out millions for TV ads. Instead, a super PAC called Fight Right was formed by an offshoot group of DeSantis supporters to handle that crucial task. Fight Right has focused almost all of its publicly disclosed spending on bashing Haley.

At a Jan. 10 debate, Haley blasted DeSantis’ campaign management, pointing to heavy turnover and extensive spending, including on private jets.

“You’ve campaigned for president in one state. You’re invisible in New Hampshire. You’re invisible in South Carolina,” Haley said. She noted that his team has spent nine figures on his campaign, yet “gone down in the polls in Iowa. Why should we think you can manage or do anything in this country?”

The campaign has consistently downplayed the drama, with spokesperson Andrew Romeo calling such reports “nonsense,” “tabloid trash” and a “false narrative.”

But for some Iowa Republicans, the missteps have pushed them away from a candidate they once saw as presidential.

A misleading assertion by DeSantis’ wife, Casey, during a Fox News interview that non-Iowans should descend on the state to “participate in the caucus” incensed some Iowans. Only they can vote in the caucuses. One county GOP leader, Kelley Koch, said her phone blew up with 52 people texting her in shock.

“They didn’t research anything — it was bad press for everybody on the DeSantis wagon,” said Madonna Johnson, a Dallas County retiree who’s active in the local Republican Party. “You can’t walk something like that back and have people believe you.”

Johnson has been to five DeSantis campaign events, including one where he signed her copy of his memoir. She’s a Trump supporter but said she would have loved DeSantis to be Trump’s running mate in 2024, and successor in 2028.

But she’s seen enough gaffes and bad decisions that in her mind, DeSantis will leave Iowa with his star dimmed. If he runs for president again in the future, she said, he should pick a different team.

“I think that Ron DeSantis has received some very sketchy advice, justified by his place in polling, and I’m really frustrated because it didn’t have to be this way,” she said. “DeSantis picked the wrong time to run, he listened to the wrong people. That’s it in a nutshell. And it’s not going to change.”