How Ron DeSantis won Florida governor

In nearly every way, DeSantis did not win by running a campaign by the book.
Ron DeSantis reacts to a high five during the DeSantis rally at the DeSantis and Scott Hillsborough County Campaign Headquarters on November 2, 2018 in Tampa.
TAILYR IRVINE | Times Ron DeSantis reacts to a high five during the DeSantis rally at the DeSantis and Scott Hillsborough County Campaign Headquarters on November 2, 2018 in Tampa.
Published Nov. 7, 2018

ORLANDO — Ron DeSantis is the Governor-elect of Florida, after a hard-fought campaign based on his sterling biography and embrace of Trumpian populism.

His victory signals the endurance of Donald Trump's Republican party in the nation's most populous swing state, dealing a punishing blow to liberals who were fired up around a potential rebuke of their state's support of the president almost exactly two years ago. But it was not so.

In nearly every way, DeSantis did not win by running a campaign by the book. While both candidates cultivated scores of national mega-donors, DeSantis didn't raise as much as Democrat Andrew Gillum. And after a comeback win in the primary himself, DeSantis faced off against an opponent whose primary victory surprised the entire state — which meant his campaign had to build a strategy against Gillum one day at a time, observers noted.

From the beginning of his career and his campaign, DeSantis, 40, a former Navy prosecutor and Tea Party congressman from Northeast Florida, has represented a rejection of the establishment and a strict ideology based in small government.

Like Trump, DeSantis' victory defied most polls that showed him trailing Gillum. Some Republican Party insiders, before Election Day, warned that the modeling of many polls predicted a too-high percentage of no-party affiliated voters in a race that would instead be more steered by those registered with the parties.

But unlike the 2016 presidential election, Gillum had a swell of progressive enthusiasm hoping for change, which proved a formidable challenge to a candidate advocating for a continuation of the same party that has held the governor's mansion for more than two decades.

In addition, DeSantis skipped his post-primary honeymoon phase when the very next morning he said that Florida voters shouldn't "monkey this up" by electing Gillum, the first black nominee of either major party in Florida's race for governor.

After several weeks of freefall, with DeSantis' connections to alleged racists constantly in the headlines, the campaign brought on Susie Wiles, a legendary Republican campaign manager who helped Trump win Florida.
After Wiles' arrival, DeSantis began to claw his way back up in the polls, though he never fully did until the final outcome told a different story.

But by the time DeSantis walked on stage to debate Gillum for the first time in October — live and in front of a national CNN audience — Wiles said she witnessed one of DeSantis' biggest strengths as a candidate, during his debate preparation.

"It's like watching an actor who can film the whole scene in one take," she said. "He can gobble up a whole issue in one briefing, and when I saw that on my second day, I thought, 'This is a whole different kind of thing.' "
She described DeSantis as a "work horse," who would read policy papers even on his rare nights at home with his two small children, sending her texts with questions all the while.

"If he doesn't have a photographic memory, it's close," Wiles added.
Trump's endorsement of DeSantis skyrocketed him to victory in the primary. In fact, during his victory speech that night in Orlando, one of his first remarks was, "Thank you, Mr. President."

But to win the general, DeSantis needed to do more than have the support of a polarizing president to win over moderates. In addition to DeSantis' resume as an Ivy-League-educated Iraq veteran, as the weeks went on, his campaign also became heavily focused on the economy and public safety — through the lens of Gillum.

Gillum took the risky step early in his campaign of unveiling a plan to add $1 billion in education funding — by raising the corporate tax rate. In the general election race, the economy became the central campaign pillar for DeSantis, who warned crowds across the state that Gillum would undo Florida's post-recession strides and might even impose a state income tax (even though Gillum has said he would not advocate for one). DeSantis also repeatedly referenced Gillum's support for Medicaid expansion, and in the primary, his support for Bernie Sanders-endorsed Medicare for All.

Essentially, DeSantis' message became that if Gillum succeeded in securing more funding to provide healthcare to more people and give teachers a uniform raise, that would cost many others in the state dearly — both in jobs and taxes.

"You've got to have good leadership and you've got to keep taxes low. Andrew Gillum, his great idea is to raise taxes 40 percent," DeSantis told a crowd of about 5,000 people on Saturday at a rally with Trump. "That will cost you your jobs, that will cause businesses to leave Florida … it would be a historic mistake."

Perhaps his earliest backer among state-level politicians was Rep. Jose Oliva of Miami, who is designated to be Florida's House speaker next year. Oliva endorsed DeSantis before the primary, when most state lawmakers were backing Agriculture Commissioner Adam Putnam.

"I would say what I've most been encouraged by is that he knows most what he believes," Oliva said of DeSantis.

He, too, said that DeSantis' victory was best foreshadowed by his debate performances against Gillum, especially when the two sparred on economic issues and DeSantis' low-tax platform was side-by-side with Gillum's proposals.

"Debates have their 'gotcha' moments back and forth… [they test] who knows what this job is, and who knows what the consequences of their decisions are," Oliva said. "The other campaign, they articulated a position of greater involvement of government in your lives and therefore a greater involvement in your wallet."

DeSantis also invariably contended that Florida would be less safe under Gillum, because of Gillum's positions on immigration and policing, as well as by repeating Tallahassee has the highest crime rate in the state. (That's not accurate. However, Leon County, where Tallahassee is located, does have Florida's highest crime rate. Tallahassee is the only city in the county.)
Then there was the drip of stories, two weeks before Election Day, that brought some new revelations about the FBI's probe into alleged corruption involving the Tallahassee city government.

"I'm … the only candidate that can say I've never had my palms greased by an undercover FBI agent while I've been in office," DeSantis said at the Trump rally.

These constant refrains prompted criticism that DeSantis' campaign was too negative, so much so that his campaign privately tried to remind DeSantis to speak about his own positive attributes before he started attacking Gillum on the stump. It was advice that DeSantis found difficult to heed.

"Negative partisanship drove this race," said Alex Patton, a GOP strategist whose client list doesn't include DeSantis. He said that both Gillum and DeSantis appealed strongest to their parties' bases.

Tim Hester, 64, of Pensacola, attended DeSantis' rally with Trump and said his vote for the former Congressman was driven in large part by Gillum's messaging.

"I would've voted for most anybody that wasn't Gillum, but I like Ron DeSantis," he said. "The 800,000 people he [Gillum] is wanting to add to Medicaid, somebody's got to pay for that. Too many people think this stuff is free."

As for the Democrats, DeSantis' win will likely leave the party in shambles, after so much talk of a "blue wave." State Rep. Blaise Ingoglia, who chairs the state's Republican Party, said it's proof yet again that the GOP in Florida is better organized.

"One of the things that helped is turnout that rivaled 2016," both in makeup and size, Ingoglia said of the early statistics based on the days leading up to Election Day. "This win by Ron DeSantis is a referendum to keep on doing what we're doing, because obviously it's working."

Times/Herald staff writer Elizabeth Koh contributed to this report