Deja Vu All Over Again

Less than two weeks ago, Jacksonville political consultant and lobbyist Susie Wiles got tasked with another in a series of political reclamation projects.

Her latest gig: saving Republican Ron DeSantis’ campaign for governor.

Polls in September showed DeSantis down. The worst had him nine points behind Democrat Andrew Gillum. And the momentum of the campaign reflected those polls. DeSantis was tanking with women and No Party Affiliation voters.

The DeSantis campaign was getting its butt kicked in every meaningful way. Message discipline? It didn’t exist, in part because the campaign is still figuring out its platform beyond MAGA and in part because the skeleton crew running the campaign wouldn’t have been enough even to win the primary without the president’s endorsement.

Wiles has been aboard only a couple of weeks, but the early results are positive for
her client.

The campaign’s messaging has moved from charging Gillum with “socialism” to more direct attacks, including spotlighting issues he’s faced as mayor of Tallahassee (such as slow-walking power restoration after Hurricane Hermine in 2016).

Is this stuff working? Polls say so.

We saw a few surveys last week that showed the race tightening up. A big part of that tightening is the classic Republican tactic: driving up the negatives of an opponent who has yet to effectively fully define himself.

Gillum was an unknown quantity to many even when he won the primary. Democratic campaigns saw him polling fourth and didn’t bother to push oppo; they cannibalized themselves, and Gillum went from being a candidate who couldn’t fund-raise to the titular head of the Democratic Party without being vetted beyond whisper campaigns (of the “I need to be off-off record here, on deep background” variety).

If you don’t take the shot, you don’t win the game. And Democratic rivals, underestimating Gillum in a way third-party groups and out-of-state money men didn’t, failed to take that shot.


Susie Wiles will not be so cavalier. And neither will DeSantis.

Consider her track record. She handled business for Rick Scott in 2010, then came
in to the Florida Trump campaign and turned that disorganized mess into a general election win.

Scott was a flawed candidate: not a ton of charisma, and lingering questions over pleading the Fifth six dozen times during a trial about his corporation’s Medicare fraud. Nasty business. You might have heard about it.

Trump? Likewise, not the best candidate. Believe me.

From the Access Hollywood blooper reel to summoning Russian spies to produce Clinton campaign emails, Trump presented like Rodney Dangerfield doing a tribute to Rodrigo Duterte. But it didn’t matter. He won. And Wiles got him over in Florida.

Wiles, unlike many Republican operatives, actually knows how to organize a campaign. When I asked Rick Scott about her going to TrumpWorld in 2016, he noted her ability to get people to volunteer.

DeSantis needs that. He had no field in the primary. Like Adam Putnam said, he was the “Seinfeld candidate,” with no reason to run beyond Being Trump’s Guy. He didn’t even have yard signs worth mentioning—a flaw about which GOP volunteer types across the state have complained, even recently.

Bet your bottom dollar: The DeSantis campaign will look like a real campaign by
the end.

In this space two years ago, I warned Clinton backers that things could get ugly for them.

“Wiles will make sure the field operations are on point. Trump putting her over Florida is a calculated decision, like giving the ball to a running back in the last drive of the fourth quarter,” I wrote.

“Whatever you may think about Trump and his batshit quote of the day,” I added, “keep in mind that the person running his Florida operation sees the whole field, and has a career’s worth of experience making chicken salad from _____.”

DeSantis spent much of the first stretch of the general election run making unforced errors. There haven’t been as many lately.

In recent years, races have tended to tighten up in favor of Republican candidates. Gillum could be the outlier here, but the path to victory is now a lot more treacherous than it was before DeSantis hired Wiles.

If DeSantis wins? It bodes well for Mayor Lenny Curry here in Jacksonville, who A) collaborates with Wiles on issues (like the 2016 Pension Tax Referendum) and B) offered a somewhat over-the-top endorsement of DeSantis as a “brother from another mother.”

For most readers, though, being better positioned for state largesse would be a meager consolation prize for losing out on the paradigmatic shift Gillum represents—if his operation can overcome arguably the best stretch-run op in local history.