It is now a truth universally acknowledged that The Courage to Be Free, Florida Gov. Ron DeSantis’ No. 1 bestselling campaign book, is boring. In an early review, Times critic Jennifer Szalai wrote that DeSantis comes across as a “mechanical try-hard” on the page and the Guardian dismissed The Courage to Be Free as a “mirthless read.” By most accounts, this makes the book a fairly accurate representation of DeSantis himself, a dogged, intelligent, and utterly charmless man who’d rather transcribe fitting quotations from the Federalist than shoot the shit in a diner with retirees in MAGA caps. The key question: Is DeSantis boring in the right way?
The Courage to Be Free minces around Topic A: Donald J. Trump, DeSantis’ main opponent in his all-but-official 2024 GOP presidential primary campaign. He writes approvingly of a handful of Trump policies—including the border wall, which DeSantis must be smart enough to recognize as a boondoggle, even if he is also too smart to admit as much. He simply avoids mentioning the approximately one million foolish, self-defeating, and disastrous actions and statements Trump made while in office, from the Muslim travel ban to “Stop the Steal.” This strategy reflects the governor’s overall attitude toward the kind of conflict on which Trump feeds. When an executive at Disney—a major industry in Florida—told DeSantis that the company’s management was being pressured by its staff to speak out against a bill prohibiting Florida teachers from discussing sexual orientation and gender identity with primary schoolchildren, DeSantis urged the man to simply ignore it. The “leftist-rage mob,” he assured the guy, would drift on to “some new outrage” after 48 hours of online furor. Ignore it and it will go away is his motto, whether the irritant is Twitter or Trump.
DeSantis’ brand is that he’s nothing flashy. He puts his head down and works hard—primarily at thwarting the nefarious schemes of what he refers to as “the regime” and “the ruling class.” What passion exists in the bland gruel of The Courage to Be Free comes in the form of resentment toward this “elite,” which DeSantis patiently explains is composed of people who may lack “tremendous aptitude, great wealth, or major achievement,” yet are nevertheless extraordinarily powerful, controlling “the federal bureaucracy, lobby shops on K Street, big business, corporate media, Big Tech companies, and universities.” They are “products of America’s ideological higher education system” and view their fellow Americans “as subjects to be ruled over, not as citizens to be represented.”
This is populism 101, with Ivy League universities and the 1619 Project replacing the Jews and the World Bank as the villains of choice. DeSantis is conservative in the sense that he is against social change, but he has no problem with big government as long as its interventions are made on behalf of his own favored ideology. Government should force social media platforms to stop (as he sees it) suppressing right-wing statements as “disinformation” because such platforms are de facto public utilities and therefore ought to be subject to regulation. DeSantis punished Disney’s opposition to Florida’s Parental Rights in Education Bill—which amounted to vague threats to withdraw campaign contributions—by cracking down on the company’s longstanding special arrangements with the state regarding the site of its theme park. Using state power to retaliate against a private company for its positions on social issues was a “troubling example of the weaponization of one of the most intrusive, powerful agencies in the federal government” back when it was the IRS investigating Tea Party groups in 2013, but it’s acceptable when “large corporations are seeking to use their economic power to advance the left’s political agenda.”
The nasty, vengeful side of DeSantis—including the cruel stunt of using state funds to fly asylum-seekers from San Antonio, Texas, to Martha’s Vineyard, Massachusetts, another incident that goes entirely unmentioned in The Courage to Be Free—certainly recalls Trump, but unlike DeSantis, Trump made vindictiveness a keystone of his political persona. Trump became the vehicle for his base’s resentful contempt for the educated, cosmopolitan professional class, and he pulled it off because his base understood that, for all Trump’s (alleged) wealth, the coastal urbanites who looked down on them also looked down on him. DeSantis is meant to be a housetrained Trump, less scattered, ignorant, and capricious. He is calm where Trump is volatile. He is consistent where Trump is unpredictable. DeSantis hates what he calls “the ruling class” on principle, because he thinks it’s morally wrong and unconstitutional. Trump—who has no grasp of the Constitution and couldn’t care less about it—hates the ruling class because they hate him.
On paper, DeSantis makes more sense as a candidate than Trump. He positions himself as a team player with a commitment to the Republican Party that transcends his own self-interest. Trump destabilized the GOP’s already uneasy coalition between staid big-business interests and angry, often batty social conservatives, and DeSantis promises to put it back together again. Yes, he went to both Yale and Harvard Law, but he has neatly turned this scarlet letter around by quipping that if he “could withstand seven years of indoctrination in the Ivy League, then I will be able to survive DC without going native!”
Trump, on the other hand, has always been a credentialist, obsessed with obtaining anything (or anyone) deemed “the very best” by the same old-school authorities he ostensibly flouts. For a constituency that claims to value diligence and common sense over woolly-headed, Ivory Tower social engineering, DeSantis ought to be the more appealing. He comes from lower-middle-class stock and a small Florida city. He played baseball well enough to win an athletic scholarship, and he served in the Navy. Trump is a real estate developer from New York with a gold-plated toilet, a lazy draft dodger whose policy views have flip-flopped wildly over the decades. When DeSantis does take an oblique dig at Trump, as in a recent speech at the Ronald Reagan Presidential Library, he limits it to the former president’s managerial style. Trump made the fluctuations of his own popularity the primary focus of his administration; DeSantis boasts that he “never looked at a single poll.” His gubernatorial administration did not “leak like a sieve.” There was no “drama” or “palace intrigue,” only “surgical precision, execution day after day after day.”
I know people who find DeSantis far more frightening than Trump, because he is intelligent, more ideological, less distractible and malleable. But what if all Trump’s flaws as an executive were, in the eyes of his die-hard base—still a significant portion of the GOP’s voters—a feature rather than a bug? Maybe they’re not interested in someone who claims a commitment to party over self. Maybe drama is exactly what they want. Nothing about Trumpolatry is rational, which may be why it has proven so tenacious. It is precisely Trump’s trollish ability to nettle the people his base hates day after day after day that makes his base love him. He is essentially an entertainer, and however boorish his public antics, countless people have confessed that in person he can be formidably charming. No one has ever said this of DeSantis, whose face-to-face skills are notoriously weak. Trump is scrappy, and his fans love to see him get into it with his many foes. DeSantis prefers to position himself as above the fray. Trump constantly talks about how great he is because he’s secretly insecure. DeSantis believes he’s smarter than everybody else.
In fact, despite his station on the opposing side of the culture wars, DeSantis bears a pronounced resemblance to the authoritarian caricature he offers of the left. He is patronizing and high-handed. He produces wonky, stuffy sentences like “It is against this backdrop that debates about ‘populism’ should be analyzed” and refers to “Wilsonian moralism.” He punishes those who disagree with him, stifling dissent and, if possible, costing them their jobs, as when he suspended a state attorney who indicated that he would not prosecute laws suppressing gender affirmation treatments and abortion. The prosecutor had been democratically elected, which indicates just how deep DeSantis’ much-reiterated respect for the will of the people runs—that is: as long as he agrees with it.
One thing this dishwater-dull book makes clear: DeSantis is no entertainer. If he isn’t dreading the moment he takes a debate stage to face off against Trump, he should be. I find myself praying that Trump won’t be indicted or convicted in any of the multifarious investigations and trials that entangle him for a couple of years so that this showdown can take place. It will be toxic and spectacular and probably terrifying. But it won’t be boring.