Experts weigh in on whether DeSantis' Iowa strategy will be enough to topple Trump: 'Hail Mary'

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Many of DeSantis’ eggs are in the Iowa basket: Lanhee Chen

Lanhee Chen and Caroline Downey discuss how Florida Gov. Ron DeSantis picked up a key endorsement for president on ‘FOX News @ Night.’

Florida Gov. Ron DeSantis recently earned two key Iowa endorsements as he continues to push campaign resources into the state, a move that political experts tell Fox News Digital is an "all in" strategy as he looks to upset former President Trump in an uphill battle that could make or break his presidential ambitions next year.

Shortly after receiving the endorsement of Iowa Gov. Kim Reynolds, DeSantis was endorsed by influential Iowa evangelical leader Bob Vander Plaats who said "there’s definitely a shot that the former president can be beat here" despite Trump leading DeSantis by at least 30 points, according to the Real Clear Politics average, with just over six weeks until the Iowa caucus. 

"Americans like winners and want to be part of winning," David Avella, chairman of GOPAC and a veteran Republican strategist, told Fox News Digital. "History tells us that the nominee will be the individual who wins at least two of the first three contests. While history also tells us that an Iowa victory is not essential, it is clear that Team DeSantis is seeking a victory to counter the inevitability of former President Trump being nominated again. It may prove effective, yet it has to work given the resources and attention Team DeSantis has put into Iowa."

DeSantis and his primary Super PAC, Never Back Down, have poured a vast majority of their resources into Iowa in a strategy that GOP strategist Alex Conant, founding partner at Firehouse Strategies, told Fox News Digital is a strategy born out of "necessity" and that recognizes the "political reality that if Trump wins Iowa" it is "hard to see how he is stopped anywhere."

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Former President Donald Trump and Florida Gov. Ron DeSantis (Getty Images)

"This is the equivalent of a Hail Mary," Conant said. "It could work like when John McCain went all in in New Hampshire in 2008, and he shocked the political world by emerging as the nominee. Barack Obama did the same thing in 2008 in Iowa when he was going up against Hillary Clinton when he went Iowa or bust, and he won Iowa and went on to win the nomination. There is plenty of precedent for a candidate going all in on one state."

Despite the historical precedent of late Iowa surges and candidates using Iowa as a springboard to the nomination, Conant said 2024 is not a "normal primary" with Trump in position as a "de facto incumbent" where he says the other candidates have so far failed to effectively explain why he should be unseated.

"The good news for Ron DeSantis is he is the front-runner in Iowa if former President Trump was not competing to win Iowa," Avella told Fox News Digital. "The bad news for Ron DeSantis is former President Trump is organizing to win Iowa. For DeSantis to win, he needs to get [there to] caucus those voters who are still keeping their options open and those voters who are only considering candidates other than Donald Trump. It is going to take him convincing voters with a clear, concise message that his ideas are the best solutions."

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Ron DeSantis speaks to members of the media after an event in Chariton, Iowa, on July 27, 2023. (Sergio Flores for the Washington Post via Getty Images)

In terms of the messaging needed for a late surge, Conant told Fox News Digital that the DeSantis campaign has been "too much about Florida."

"The truth of the matter is people in Iowa don't care about your record in other states. They want to know what you're going to do for them as president," said Conant, who served as communications director for Florida Sen. Marco Rubio’s campaign that came close to winning Iowa after a late surge in 2016.

"Republican voters are clear that the cost of everyday living and failure with border security are their top concerns," Avella said. "Ron DeSantis has to convince voters with a clear, concise message that his ideas are the best solutions."

Ashley Hayek, executive director of America First Works, told Fox News Digital that DeSantis’s strategy in the next few weeks is "irrelevant" with the outcome "already decided" thanks to Trump’s "significant influence" in the Republican Party.

"Voters are nostalgic for the economic successes under Trump, often referred to as ‘Trumpanomics,’" Hayek said. "It's akin to a company rehiring a former CEO who previously steered them through prosperous times; the familiarity and proven track record are irresistible. The Republican nominee is essentially pre-decided with Trump's rehire on the horizon by early 2024."

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Former President Donald Trump greets supporters as he arrives at the Iowa State Fair on Aug. 12, 2023, in Des Moines. (Fox News / Paul Steinhauser)

Several prominent DeSantis donors told Fox News Digital this month that they were encouraged by how he was campaigning in Iowa and expressed the belief that Iowa voters are just now starting to pay close attention to the January caucus. 

In a statement to Fox News Digital, DeSantis Communications Director Andrew Romeo said the Florida governor is the only candidate who can beat Trump regardless of where the primary is.

"Ron DeSantis is the only candidate with the organization, resources, and message necessary to beat Trump in multiple early states - including the first and most important state on the calendar," Romeo said. "That's why Team Trump continues to attack him every day." 

The super PAC backing Trump's campaign revived attack ads against DeSantis last month, spending millions going after DeSantis in the past few weeks, which Romeo referred to on social media as a public admission that DeSantis is "climbing in Iowa."

DeSantis surrogates have made the case that polling is different from turnout and that responding to a poll is different from actually showing up on a cold winter night in Iowa to caucus for a candidate.

Several prominent DeSantis donors told Fox News Digital that they were encouraged by how he was campaigning in Iowa and expressed the belief that Iowa voters are just now starting to pay close attention to the January caucus. (Scott Olson / Getty Images / File)

"It will take a turnout operation unlike any in electoral history to get voters to show up on a cold night to vote for a candidate who is down 15 points," Avella said.

If DeSantis is to make a late surge, Conant said a "strong third" or "distant second" "isn’t going to cut it against Trump," especially with DeSantis polling as low as fifth in New Hampshire and South Carolina being strong states for Trump and former South Carolina Gov. Nikki Haley.

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Avella concurred and said Trump has "such a commanding lead that even a second-place finish may not be enough to alter the current likely outcome."

"The real question is how much is a second-, maybe third-place finish in Iowa worth?" Hayek said. "Despite rounds of layoffs that were part of a widely publicized ‘reset,’ DeSantis has burned through more primary cash than he raised over the last three months. The DeSantis campaign’s spending strategy shows they see the writing on the wall: there is not enough gas in the tank for New Hampshire or South Carolina, and at this rate, there is not going to be enough for Iowa either."