Ninety-one criminal charges spanning four cases later, it has become clear Trump was stronger than ever. He
broke fundraising records off of his Georgia mugshot, sailed in poll after poll and campaigned on an adopted martyr persona. DeSantis was left to all but defend Trump, while attempting to persuade Republicans he had become a more viable option in a general election.

The Florida governor, known nationally as a bulwark against federal Covid policies, also found himself defined by the former president. Trump’s campaign and political action committee went after DeSantis in a highly organized, effective — and expensive — way, months before the Florida governor even got into the race and at a time when he was legally barred from responding to criticisms under federal elections laws.

Then DeSantis, 45, botched his May 2023 entrance into the presidential campaign by launching in
a glitch-saddled appearance on X rather than showcasing his young, telegenic family at an in-person event.

DeSantis lost traction in the months ahead. By July, his campaign had to announce rounds of layoffs, leadership shake ups and what they described as a “
reload.” November carried leaks about the
internal drama that surrounded Never Back Down, the super PAC supporting his candidacy. Several news outlets closed out the year with DeSantis’
political obituary.

“There’s a lot of false narratives that are out there,” Scott Wagner, chair and CEO of Never Back Down, told POLITICO during an interview when asked about campaign missteps after the Iowa caucuses were called for Trump. “And there’s a lot of false narratives that are pushed by people who have different agendas. I don’t think the governor’s campaign has been a bad campaign. I think it’s been a good campaign. He’s done things the right way.”

The DeSantis campaign did not immediately respond to a request for comment.

DeSantis’ biggest miscalculation may date back to 2019, when he fired his political operative, Susie Wiles, during his first term under accusations that she leaked a
fundraising document, which she denied. Trump later hired Wiles, a seasoned operative deeply connected in Florida, to run his presidential campaign alongside Chris LaCivita. Together,
they wielded a disciplined, orderly and decidedly un-Trumpian campaign.

They also had the advantage of bringing in seasoned experts
DeSantis had dumped, including former aide Justin Caporale, former deputy chief of staff James Blair and
Florida director Brian Hughes. In an early sign of how they planned to embarrass the governor on his home turf, the Trump campaign collected endorsements from Florida’s congressional delegation right as DeSantis was
set to visit DC and before he had the power to court endorsements because he hadn’t formally entered the race. After that, they began aggressively wooing Florida’s grassroots Republicans.

While the endorsements may not have had any effect on the average Republican caucus goer in Iowa, they showed an intimate knowledge of what made DeSantis tick and gave the impression that he was unprepared and disconnected from his home state.