In Jacksonville, Florida, Republican politics were relatively subdued about nine years ago. Donald Trump was still a shocking figure to many in the “chattering class,” with people questioning why Susie Wiles—a level-headed moderate respected by those who don’t usually embrace populist figures like Trump—was working for his campaign. During a quiet lunch, I asked her why she supported Trump. She calmly explained how he was a viable nominee and would eventually become president.
Conventional wisdom suggested that Wiles was wrong, but as often happens, the conventional wisdom proved to be outdated garbage. Wiles joined Trump’s campaign just before a Jacksonville rally largely ignored by the city’s GOP elite, who believed in Jeb Bush or Marco Rubio—two candidates she referred to as “incrementalists.” Wiles was proven right by the voters, much like she had been when she worked for then-candidate Rick Scott in 2010.
Like Trump, Scott was an independently wealthy political outsider who overcame primary opposition that had every meaningful endorsement and won the election. In 2016, history repeated itself as Wiles took on more crucial roles within the campaign. Her organization skills and ability to attract volunteers helped her succeed in Florida, setting the stage for Republican victories ever since.
In September 2018, Wiles was tasked with rescuing another underperforming candidate: Ron DeSantis, who appeared unlikely to defeat Andrew Gillum in the polls. Despite a Trump endorsement that powered him through the primary against Adam Putnam, DeSantis still found himself down by as many as 9 points after the August primary. However, Wiles’ work helped turn things around for him.
Unfortunately, DeSantis failed to appreciate her efforts and eventually removed her from his orbit for unfounded reasons. As he began his book tour/presidential campaign—an attempt to clear the field and a bet that Trump wouldn’t be able to run for legal or health reasons—DeSantis soon found himself in a precarious position, unable to win any counties in Iowa.
As we look ahead to the 2024 presidential election featuring a rematch between Trump and Joe Biden, it is clear that the conditions on the ground reflect those of 2016’s battle with Hillary Clinton. While much of the media still runs cover for Biden, Trump doesn’t have to manage a pandemic against the backdrop of Black Lives Matter demonstrations in every major city. People are starting to remember when their dollar bought more and the relative foreign-policy stability that existed during Trump’s presidency but is absent today due to ongoing conflicts in Ukraine, Chinese aggression in the Pacific, and Russian provocations off the Florida coast.
For the first time in years, Susie Wiles has a lead as Trump’s fundraising continues to surge. He is building new and unexpected coalitions, so underestimating him—and his top operative—is unwise.
