Ron DeSantis' genius plan goes sideways: Is his 2024 campaign suddenly in trouble?

Martha's Vineyard gambit looks worse every day — and down at Mar-a-Lago, an embattled orange man loves to see it

By Heather Digby Parton


Published September 23, 2022 9:55AM (EDT)

Florida Gov. Ron DeSantis (Jeff Swensen/Getty Images)
Florida Gov. Ron DeSantis (Jeff Swensen/Getty Images)

Last week when I wrote about Florida Gov. Ron DeSantis' sadistic little trolling exercise — coercing asylum seekers to board a plane for Martha's Vineyard, purely to own the libs — I speculated that Donald Trump must have been gnashing his teeth over  his former protégé stealing the idea from him. That was true, as it turned out. Rolling Stone reported that Trump was furious, claiming that he'd tried to do something similar as president but the bureaucrats wouldn't let him. Of course, Trump was also livid that DeSantis was getting all the attention on right-wing media.

Well, he needn't have worried about losing the spotlight. This week all the attention pivoted back to Trump as numerous legal crises descended upon him and DeSantis faded into the background. Which was a lucky break for the Florida governor, honestly. Some rather unsavory facts have emerged in the last few days about his Martha's Vineyard stunt, shedding light on who may have profited from it as well as what he had hoped to achieve with an aborted flight to Delaware — President Biden's home state — that was supposed to happen a few days later.

This story is still unfolding, but the more we learn, the uglier the whole thing looks. Payments for the Martha's Vineyard flight apparently went to some big-donor cronies with connections to the DeSantis administration, and no one has yet figured out who hired the shadowy characters in Texas who made all kinds of false promises to asylum seekers to get them on the plane. The Miami Herald is all over this and I'm sure their reporters will dig up more very soon.

As for the Delaware flight, it was originally scheduled to take off from San Antonio on Tuesday, with the same shady characters luring unsuspecting migrants onto the plane. Then it was abruptly canceled, possibly because word got out and authorities in Delaware government were prepared to receive them. Some in the press have swallowed the line that the plan was to "punk" the Delaware libs by making them get ready for a bunch of migrants and then landing an empty plane in New Jersey, which strikes me as ridiculous. Potential passengers had already been recruited, who were left high and dry when the plan was canceled at the last minute. It seems far more likely that DeSantis and his accomplices started to feel the heat and decided to call the whole thing off.

There are various questions about the legality of this scheme. A sheriff in Texas has opened a criminal investigation and a nonprofit has filed a lawsuit against DeSantis on the migrants' behalf. When it became clear that these migrants were asylum seekers fleeing the dysfunctional left-wing government in Venezuela, DeSantis likely became worried about the political optics, and about upsetting an influential Republican constituency. Florida has a lot of Venezuelan immigrants opposed to the current regime in their home country.

This whole ruse was designed to get the media talking about immigration and the border just ahead of the midterm elections, and I suppose it may have achieved that end. But it also exposed DeSantis, once again, as a snotty troll, and his act may be wearing thin with people who don't have the emotional development of 12-year-old bullies. Naturally, the hardcore Trump base loved it. But can he sustain that love the way Trump has?

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The New York Times' Jamelle Bouie wrote recently about DeSantis' culture-war stunts, from his war on Disney for being "woke" to ordering Florida schools to indoctrinate students with the right-wing propaganda version of American history. It seems to be pretty much the only thing DeSantis does these days, and he certainly attracts tons of attention flitting from one invented battleground to another without pausing for breath.

But Bouie pointed out that DeSantis' most recent maneuvers haven't work out the way he hoped. Sure, he got his photo-ops and national media attention, which he craves more than anything, but the results weren't likely to play well with normal people. His "election police" arrests of alleged illegal voters turned out to represent failures by his own officials, who had registered a small number of voters who weren't eligible. And the Martha's Vineyard ploy, rather than showing horrified liberals screaming to get the Latinos off their lawns, instead showed a small community responding with empathy and compassion, which undercut the desired narrative about hypocritical liberal elites. In Bouie's view, DeSantis isn't ready for prime time:

Yes, when viewed from the perspective of partisan media, DeSantis looks almost unstoppable. But to a typical person — someone who may have heard about these stunts but doesn't know much about DeSantis otherwise — he looks a lot like a bully, someone willing to play high-stakes games with people's lives for the sake of his own ego and advancement.

Well, you might say, Donald Trump is a bully, too. Yes, he is. But Donald Trump is also a lifelong celebrity with a public persona that is as much about "The Apprentice" and even "Home Alone 2" as it is about his political career. What's more, Trump has the skills of a celebrity. He's funny, he has stage presence, and he has a kind of natural charisma. He can be a bully in part because he can temper his cruelty and egoism with the performance of a clown or a showman. He can persuade an audience that he's just kidding — that he doesn't actually mean it.

That's an astute observation. Trump is a nasty piece of work: a crybaby, a braggart and an ignorant fool. To his large and devoted following, he's also wildly entertaining, which is a huge part of his appeal. In fact, that's the most important part of his appeal. Yes, he has given former fringe elements on the right permission to let their freak flags fly and flaunt their hatred. But when he says "there's nothing more fun than a Trump rally," for his fans that's absolutely right. Trump's roadshow is their rolling Woodstock, their Grateful Dead.

Now tell me if this guy has an ounce of fun in him:

DeSantis gave a speech to big donors about two weeks ago in which he telegraphed his plans to send migrants to Martha's Vineyard and made clear that he plans to run for president in 2024 as an unreconstructed culture warrior. His speech sounds like Pat Buchanan, back in the latter's glory days of the '80s and '90s. But Buchanan in person could be garrulous and funny, a classic Irish-American backslapper and glad-hander, which made up somewhat for his hardcore hate-mongering. DeSantis has none of that personal charm:

DeSantis did not joke with the crowd, or thank his hosts, or even wait for applause at times as the audience cheered him, according to multiple people familiar with the gathering. In a private roundtable with top donors, he mainly gave the same speech he gave to the larger group. He was at the retreat for about three hours. Several people familiar with the event said he received mixed reactions from donors, who liked his broader message but wished he would connect more personally.

Say what you will about Trump, but his celebrity glamour definitely works on some people and no one would claim he lacks a gift for showmanship. DeSantis, on the other hand, is a creepy, dour, unlikable jerk. While the Trump cult does love an asshole, they want one in the vein of a wrestling "heel," who makes them feel good about being bad.

Ron DeSantis wants to be president and he's adopted the latest right-wing ideological fad, "Orbánism," meaning the doctrines of "illiberal democracy" borrowed from the current regime Hungary. That's definitely dangerous. But there is a political graveyard full of Republican Great White Hopes who felt sure they could be elected president until they came face to face with actual voters: Scott Walker, Fred Thompson, Lamar Alexander, Rudy Giuliani; the list goes on. Ron DeSantis may well be the next member of that ignominious club. 

Read more on the Jan. 6 committee:

By Heather Digby Parton

Heather Digby Parton, also known as "Digby," is a contributing writer to Salon. She was the winner of the 2014 Hillman Prize for Opinion and Analysis Journalism.

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Commentary Donald Trump Elections Martha's Vineyard Republicans Ron Desantis