“I Have Never Seen a Worse Campaign and Candidate”: What Campaign Flacks Think of DeSantis 2024

DeSantis looks downward, his brow furrowed, in front of his bus, wearing a DeSantis for President fleece vest
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Republican Florida Gov. Ron DeSantis’ gentle slide from “serious presidential contender” toward “guy who might end up competing with Doug Burgum to avoid polling at 0 percent” has become less gentle in recent weeks. The first Republican debate, on Aug. 23, could be Meatball’s best and last chance to show primary voters what it might feel like to have a presidential nominee who isn’t Donald Trump. This demonstration would seem, by necessity, to require that he actually, finally, compare himself to Trump directly and explain to voters why he is a better candidate.

How should he go about doing that? What could DeSantis say to Republican voters about Trump’s weaknesses as a candidate (and as, you know, a president and citizen) that would persuade them to leave him behind in the dustbin of history or the dustbin of jail? Slate put the question to four of America’s best-known political strategists. (OK, three of America’s best-known political strategists and a friend of Slate’s who works in Democratic politics and agreed to participate anonymously.) What would they tell DeSantis if they were working for him?

“I would advise Ron DeSantis to thank voters for their consideration and remove himself from the race,” said Alex Castellanos, a longtime Republican consultant (Bob Dole, George W. Bush) and CNN commentator. He elaborated: “There is no good way for DeSantis to attack Trump about Jan. 6 or anything else. There is no point in chaining a goat to a stake in front of a T. Rex, then asking the goat to assault the T. Rex. It has not worked out well for other goats, many stronger and smarter than this one.” Here, Castellanos’ response went into more detail about Trump’s electoral history. “So, no,” he concluded, “I would not advise the candidate who lost to the Mouseketeers to attack the T. Rex.” (Disney’s lawsuit against the state of Florida over DeSantis’ effort to revoke Disney World’s special tax status is ongoing.)

Joe Trippi, a longtime Democratic consultant (Howard Dean, Jerry Brown) who has also appeared on CNN, was more direct: “I would tell DeSantis the hard truth. In my 40 years in presidential politics, I have never seen a worse campaign and candidate. He should withdraw from the race.”

Ha-ha! Indeed, between the strong candidate ahead of him and the ineffectiveness of his own work, DeSantis is in a tough spot. As Slate’s anonymous operative put it, “You have a total charisma-vacuum of a candidate running on a niche message that only makes any sense—let alone appeals—to the very worst people on the planet. If he wants to win, he should try being an entirely different person.”

But, as noted in the Bulwark recently by ex-Republican operative Tim Miller, the potential timing of one or more Trump criminal trials during the 2024 primary season gives even the weaker candidates running against him an incentive to stay in the race and accumulate as many convention delegates as they can. Should the outcome of one of these trials (or the evidence presented therein) cause the bottom to fall out of Trump’s general-election polling, there could be panic in the GOP, and if there’s panic, there could be an effort to nominate someone else at the party’s convention.

I contacted Miller to see what he’d recommend that DeSantis say about Trump, in the meantime, to try to remain viable. With the caveats that he’s “deeply skeptical” it will work and does not personally believe what he’s written, particularly as regards Biden ruining the country or having dementia, here’s the script Miller suggested:

If Donald Trump was able to win the election and beat the deep state, he would’ve done it. There’s a reason he’s golfing every day while Joe Biden is in the White House ruining America. The only reason Jan. 6 happened is because Trump failed us: On COVID, on the border, and in his reelection campaign. It should’ve been easy to wipe out Joe Biden, but Trump couldn’t do it because he was asleep at the wheel.

I won in Florida by 19 points while all the Trump-endorsed candidates were losing. We learned in Florida that the Democrats can’t steal the election when we are kicking their ass. Give me a chance to go toe-to-toe with Dementia Joe Biden and I’ll show you how it’s done. Then when we send him off to retirement, we can actually secure the border, eradicate the deep state, and spend 8 years saving this country.

Adds Miller: “I think the time for this message was after Jan. 6 and again after the midterms.” Indeed, those were the two occasions since his 2020 loss that Trump could have been described, with the most empirical justification, as a loser or a liability to the Republican cause. Motivated either by an assumption that presidential campaigns shouldn’t start until a certain moment on the calendar or a calculated decision to try coming across as inevitable and above the fray, DeSantis chose not to engage at either moment. It’s probably not a mistake a Tyrannosaurus would have made.