‘Started on third base and stole second’: How DeSantis spent $160M to become less popular

Doing a post-mortem on a man before he dies is certainly unconventional, but in the case of Ron DeSantis, it feels more than appropriate. Vultures have been circling the Florida governor’s purpling presidential corpse for some time now, and for good reason.

He’s had trouble connecting with voters, which has made it nearly impossible for him to upload their consciousness to the mothership. He looks like he learned to smile by watching circus chimpanzees getting their backs waxed. He has the charisma of a falafel and none of the spice. And that laugh! It’s like he bought it as a 99-cent ringtone and immediately discovered the file was corrupt.

But as a new HuffPost story on the meteoric rise and fall of the DeSantis campaign shows, DeSantis isn’t copping to any of that. The biggest reason he’s had trouble getting traction, according to DeSantis and his apologists?

His top opponent, Donald Trump, is (allegedly!) a criminal. And that’s a tough hill for any challenger to climb.


DeSantis’ campaign and super PAC have spent more than $160 million to boost him, and he spent the better part of 2023 on the road. But, he now says, it may not have been enough to overcome the advantage he believes Trump received from getting indicted four times.

The line is working, at least with some.

“The race was decided totally out of their control,” said one DeSantis donor and supporter who spoke on condition of anonymity. “Trump got indicted. And indicted and indicted and indicted. The race was over after the first indictment.”

To be fair, Trump’s fake rakishness, and the perception that he’s being unfairly persecuted, did give the ex-president a boost—largely because Republican voters aren’t the most discerning lot. Everyone from Trump to Nikki Haley to DeSantis to Sen. John Kennedy knows this, and they take full advantage.

A savvier man than DeSantis might have decided it was better to treat Trump’s alleged criming as a vulnerability than a badge of honor. Unfortunately for DeSantis, he went the other way.

As HuffPost’s S.V. Date points out, when Trump’s Florida resort Mar-a-Lago was raided by the FBI because he was holding onto top secret government documents that didn’t belong to him, in defiance of a subpoena, DeSantis—who, again, is running against Trump—rushed to Trump’s defense. 

He used that time-tested GOP technique of making it about Hunter Biden, tweeting, “The raid of MAL is another escalation in the weaponization of federal agencies against the Regime’s political opponents, while people like Hunter Biden get treated with kid gloves.”

See? I stand just like Trump!

DeSantis certainly knew better—as Date notes, his experience as a naval JAG officer “should have given him an understanding of what it takes to get a judge to approve a search warrant”—but he decided to stick with the fake outrage so as not to rouse the MAGA mob against him.

Later, when Manhattan District Attorney Alvin Bragg indicted Trump for falsifying business records in connection with the hush money payment he made to adult film star Stormy Daniels, DeSantis pounced on Trump’s behalf, saying he would steadfastly refuse to extradite Trump from the Florida swamps.

And to this day, DeSantis has remained reluctant to exploit Trump’s alleged crime spree—even after Trump was charged with 91 felony counts across four separate jurisdictions.

“If you can’t learn from history, you can’t change the future,” said one Republican consultant who spoke to HuffPost anonymously, noting that Trump’s 2016 primary rivals also failed to exploit his glaring vulnerabilities until it was far too late. “The only way to take out Donald Trump is to take him on.”

But even though DeSantis carried Trump’s water when he should have been waterboarding him (metaphorically, of course!), there may have still been an opening for the candidate who polled within 8 points of Trump as recently as January. 

But then DeSantis started campaigning. And even $160 million in outlays from his campaign and super PAC weren’t nearly enough to overcome his clear deficiencies.

RELATED STORY: Ron DeSantis’ Never Back Down PAC is … well… backing down

“He started the primary on third base and stole second,” David Jolly, a former Republican congressman from Florida, told HuffPost. “We’ve now witnessed one of the most expensive and embarrassing collapses in Republican history.”

KISSIMMEE, FLORIDA - NOVEMBER 04: Republican presidential candidate Florida Gov. Ron DeSantis speaks during the Florida Freedom Summit at the Gaylord Palms Resort on November 04, 2023 in Kissimmee, Florida. The Republican Party of Florida hosted the summit as candidates continue to campaign across the country. (Photo by Joe Raedle/Getty Images)
Hi! I’m Ron DeSantis!

Some of DeSantis’ detractors noted that he spent too much time attacking Disney and COVID-19 doctors—and not nearly enough calling out the GOP frontrunner. 

“He tried to ‘out-Trump’ Trump among Trump supporters instead of going for the ‘maybe Trump/move on from Trump’ voters, and it was a fatal strategic choice,” said Fergus Cullen, a former chair of the New Hampshire Republican Party.

If those assessments seem harsh—well, there’s a reason. DeSantis has been a uniquely bad candidate, and that’s been on lurid display for all to see. Remember that “war on woke” he lost?

The HuffPost story includes a treasure trove of amusing quotes highlighting DeSantis’ ineptitude and crushing lack of charisma. As Date notes, DeSantis was polling better before he started campaigning in earnest, and “the more voters saw of him, the less inclined they were to support him.”

“The idea of ‘a’ DeSantis was appealing, but the reality of ‘the’ DeSantis was repellent,” Mac Stipanovich, a Florida politics veteran, told HuffPost. “It is telling that his favorite president is Calvin Coolidge, the avatar of anti-charisma in politics.”

Consider what the Heritage Foundation said about ol’ Silent Cal in 1996:

[The Republican National Convention of 1924] is generally remembered as the most uninteresting convention in Republican history. Delegates didn’t bother showing up at many of the sessions. The most popular drink was a keep-cool-with-Coolidge highball, composed of raw eggs and fruit juice. Will Rogers suggested that the city of Cleveland “open up the churches to liven things up a bit.”

But this is a reminder that politics, in the end, is not about drama but about principle, not about charisma but about character.

And this was BEFORE he was described as “the most articulate conservative who ever served as President.”

DAVENPORT, IOWA - NOVEMBER 07: Republican presidential candidate Florida Governor Ron DeSantis speaks to the press following a campaign event at the Machine Shed restaurant on November 07, 2023 in Davenport, Iowa. Iowa voters will be the first in the nation to choose their nominee for Republican presidential candidate when they go to caucus on January 15, 2024. (Photo by Scott Olson/Getty Images)
Can we just pretend the backdrop says “DeSantis for Resident?” ~Ron DeSantis, probably

But back to DeSantis. Republicans remain uncharitable toward the weird-booted warrior.

“When you come across as a mean person who shows little empathy for the real concerns for citizens, and who always wants to make sure everyone in every room knows you think you are the smartest person there, it doesn’t go over all that well,” Steve Duprey, a former Republican National Committee member, told HuffPost’s Date. “Focusing on Disney, wokeness, a little hippie college in Sarasota, and an abortion ban out of sync with most of America, instead of on the economy, the debt, the border, isn’t a winning formula. … Other than that, he’s nailing it.”

Another Florida Republican who spoke on condition of anonymity offered, “Who was he? Was he for Trump? Was he against Trump? Was he courting Trump voters? Is he more practical, sensible? Or he is a right-wing nut? I don’t know. But he’s just not likable.”

And as The Nation noted this week:

The pledge to “make America Florida,” to cite DeSantis’s own MAGA-riffing campaign mantra, just served to underline the unshakable longing among the party’s base to make America Trump country.


So much, in other words, for the “Make America Florida” project. Indeed, one key reason DeSantis has managed to argue himself into that deeply untenable initiative is that Florida on his watch has become something of a Potemkin model of right-wing governance. Along with all the other authoritarian entries in his governing portfolio, DeSantis has signed into law severe restrictions on ballot access and has overseen a gerrymandering scheme that’s since been found unconstitutional. What this means in practical political terms is that DeSantis’s claims to runaway success, together with the legislative GOP supermajorities that have supinely enacted his agenda in the state, are something of a mirage. The moment DeSantis’s program was on course to reach a national audience, it was destined to flame out, regardless of the internal machinations of super PACs, donor cattle calls, Iowa ground games, and the like. And for all of DeSantis’s richly deserved anguish and humiliation on the national stage, that’s also an encouraging moral for the rest of us.

DeSantis’ Florida-flavored Fox News clout never translated to the campaign trail, where the governor was forced to interact with real people who asked real questions.

“To me he never looked very happy,” an anonymous Iowa political operative and supporter told HuffPost.

And while Trump’s post-indictment boost was real, and DeSantis’ fake-populist approach may have been misguided, in the end, DeSantis’ biggest obstacle was likely DeSantis himself. 

“A few of my congressional staff worked for him, and we all said the same thing,” former Illinois Rep. Joe Walsh added. “He’s just weird. Doesn’t know how to just normally interact with people.”

Really? Weird? This guy? You don’t say!

Sadly—for Floridians—once he ends his failed campaign for the White House, DeSantis will go back to Florida, where he remains the governor, while his constituent Trump will remain the GOP frontrunner.

Check out Aldous J. Pennyfarthing’s four-volume Trump-trashing compendium, including the finale, Goodbye, Asshat: 101 Farewell Letters to Donald Trump, at this link. Or, if you prefer a test drive, you can download the epilogue to Goodbye, Asshat for the low, low price of FREE.


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