JACKSONVILLE, Fla. — Around nine years ago in Susie Wiles’ hometown of Jacksonville, Republican politics were a bit more muted than they are today.
Donald Trump was still shocking to many, especially those of the chattering class, and there was considerable consternation as to why Wiles — known as a level-headed moderate and widely respected by the kind of people who don’t embrace populist figures like Trump — was working for his campaign, helping to run the Florida operation.
Over a quiet and not terribly expensive lunch not far from City Hall, where she was helping recently elected Lenny Curry with his 2015 mayoral transition, I asked her the obvious question to many: Why Trump?
She calmly and lucidly explained not just why he was a viable nominee — but why he would be president.
Conventional wisdom said she was wrong. But as often happens, the conventional wisdom was outdated garbage.
She was methodical in joining the campaign, just before a Jacksonville rally largely ignored by the city’s GOP elite, who believed in Jeb Bush or Marco Rubio — two worthy men she called “incrementalists.”
And she was proven right by voters. Just as she had been before.
Those who saw the work she did for then-candidate Rick Scott in 2010 shouldn’t have been surprised.
Like Trump, Scott was an independently wealthy political outsider who overcame primary opposition that had every meaningful endorsement and then won, in part because she matched the candidate’s now well-known work ethic on the strategic side.
In 2016, history repeated. And Wiles took on ever-more-important roles, handling “battleground communications” for the campaign by the end of August and then taking sole command of the Florida operation down the stretch — efforts that not only won the state in that cycle by tamping down on unforced errors but set the stage for Republican victories ever since.
“What Susie’s good at is organization. She’s good at getting a lot of people to volunteer. She’s going to do a great job,” now-Sen. Scott told me as she took the leadership role.
And he was right.
In September 2018, Wiles was charged with rescuing another underperforming candidate: Ron DeSantis, who didn’t look like “DeFuture” in polls against Andrew Gillum, a Tallahassee Democrat seen for a moment as a potential national player.
Despite the Trump endorsement that powered DeSantis through the primary against Adam Putnam, polling saw the Republican down by as many as 9 points in the weeks after the August primary.
Again, Wiles worked her magic. Unlike Trump, DeSantis didn’t appreciate her efforts in the same way, and she was soon enough excommunicated from the governor’s orbit for spurious reasons — discarded like so many operatives were along the way.
DeSantis eventually came to regret that, of course.
After a laugher re-election campaign against the enervated Charlie Crist, the bills came due when he began his book tour/presidential campaign, an effort to clear the field and a bet that Trump wouldn’t be able to run for legal or health reasons.
DeFuture soon enough became DePatsy, with Wiles helping to define her former client on Trump’s behalf.
DeSantis World had no counter, and his campaign burned roughly $150 million to win not a single county in Iowa, a state where it ended up betting everything — to no avail.
Though the 2024 ballot features a rematch between Trump and Joe Biden, the conditions on the ground reflect 2016’s battle with Hillary Clinton.
While much of the media still run cover for Biden just as happened in 2020, Trump isn’t having to manage a pandemic against the backdrop of Black Lives Matter demonstrations in every major city.
And people seem to be taking the longer view of his entire presidency, remembering when their dollar bought much more than it does at the end of the current president’s term and a relative foreign-policy stability we don’t see today with ongoing conflict in Ukraine, Chinese saber-rattling in the Pacific and Russian provocations off the Florida coast.
For the first time in years, Susie Wiles is playing with a lead. Trump’s fundraising is surging, and he’s building new and unlikely coalitions.
Underestimate him — and his top operative — at your peril.
