John Raoux/AP Photo
Then-U.S. Rep. Ron DeSantis answers questions from reporters after a Florida Republican gubernatorial primary debate, June 28, 2018, in Kissimmee, Florida.
The Courage to Be Free: Florida’s Blueprint for America’s Revival
By Ron DeSantis
Broadside
I first met Ron DeSantis in September 1997, the first week of a new school year at Yale. DeSantis was a freshman recently arrived on campus, and I was a sophomore.
Our business together at Yale was playing baseball—the only reason we were both ever admitted to the school. That week, the upperclassmen on the team rounded us up for an informal practice. It was the chance to check out the new guys.
I recall that “D,” as he introduced himself, showed up to the field wearing a T-shirt and jean shorts—an unforgettable outfit. DeSantis still remembers it, too. He writes in his memoir, “The day I finally stepped foot on the Yale campus was a massive culture shock for me. I showed up on my first day wearing a T-shirt, jean shorts, and flip-flops. My usual attire back home in Florida did not go over well in this new crowd, with students largely drawn from wealthy communities on the Eastern seaboard and the West Coast.”
D’s dress did not go over well. He was teased. I recall him being sullen, a bit removed. But he was there. No one ever missed this first, technically voluntary practice. Our team was tight-knit. It drew us all in, separating us from Yale social life. Few resisted the pull. I did not, and neither did D. Soon enough, he was one of us.
At Yale, across four years of practices, games, meals, and hours simply spent hanging out, I cannot remember a single discussion about politics. I had no idea D, or anybody else, had fervently held political beliefs, let alone what they might have been.
What were we doing instead? Playing baseball. Talking about women. Wasting time. Lingering over dining hall meals to continue endlessly running conversations. We watched the same movies repeatedly. A Few Good Men was D’s favorite, and to me the authenticity of the author of The Courage to Be Free was vindicated when DeSantis compared his post–Harvard Law School job as a Navy lawyer to the character played by the actor Kevin Bacon.
We handed out nicknames, ranging from the obvious (I was “Lev”) to the bizarre (“Bobblegock”) and cruel (“Pussface”). We created our own language of inside idiomatic expressions. Once, bored on a bus trip, we decided to attach the letters “er” to any word ending in “a.” Sitting on the sofer, I ate some pizzer … D spoke of Florider whenever possible. Mercilessly, we goaded and pranked each other. We bullied one other, and we loved each other, too.
There was a pecking order. As a rule, the better players on the team were protected from the worst abuse. So were the witty. Wisecracking was the most prized activity of all. D was a very good baseball player (DeSantis makes sure to inform the reader he batted .336 his senior year).
That helped his social case. Still, I recall those jean shorts so clearly because when I saw them, I thought, this guy is going to get crushed. But he didn’t. He blurred into the background, a non-presence for a time. Until, aided by his baseball talent and smarts, he learned the rules of our social game. Soon, he emerged near the top of the heap.
Of course, I am only describing the male bonding rituals of a typical American sports team of that time. But it is not possible to understand the trajectory of Ron DeSantis the politician without making sense of our time at Yale. It took place during the late 1990s, during, as DeSantis notes, “the peace and prosperity of the post–Cold War years,” when “as a country, we seemed to have not a care in the world.” These were, it seemed back then, calm years—after the fall of the Berlin Wall but before Bush v. Gore, 9/11, the war in Iraq, Hurricane Katrina, and the financial crisis of 2008 curdled the national mood.
DeSantis writes that the 1990s Clintonism of our Yale years failed “the lives of most Americans.”
The Courage to Be Free is more campaign document than memoir, of course, meant to certify his populist credentials. Not an easy feat for a Yale and Harvard grad. Many of DeSantis’s descriptions of the Yale of the late 1990s are wild exaggerations. At Yale, he writes, “we were led to believe that communism was superior.” “Around campus, there was nothing wrong with flying Soviet flags, wearing Che Guevara shirts, and paying homage to Mao Zedong.” None of this rings true. But the distortions are revealing. “In retrospect,” DeSantis writes, “Yale allowed me to see the future.” D might not have been very political in those years. But it was clearly there, at 1990s Yale, that DeSantis’s political sensibilities were formed.
For back then, something went wrong at Yale—something emblematic, which foretold the country’s future path. DeSantis, because he is a right-wing Republican governor of Florida in the middle of a presidential campaign, calls what went wrong the “unbridled leftism” of an “arrogant, stale, and failed ruling class.” I—a politically left history professor at the University of Chicago who spends most of his days alone in his study quietly reading and writing books, including about this era of U.S. history—would put it differently. Instead of “unbridled leftism,” I recall arrogant “third-way” Clinton-era liberalism.
DeSantis writes that the 1990s Clintonism of our Yale years failed “the lives of most Americans,” referring to those who did not attend Yale or places like it. He has a point.
Bill Clinton hailed from rural, poor Arkansas—a region left behind by New Deal–era American economic development before it became fertile ground for the rise of Walmart. Clinton ran for the presidency advocating what today would be called “regional” or “place-based” economic policy, but years into his presidency made an abrupt political turn. His administration abandoned the fledgling labor movement for booming Wall Street (and Walmart).
Clinton went all in on a high finance–led globalization, letting the regional economic chips fall where they may. Liberals began to promise equality of opportunities, leaving outcomes to take care of themselves, too. The gospel was meritocratic. Higher education was the ladder to success. Accordingly, institutions like Yale began to open their doors, admitting more students from outside the traditional East Coast elite.
When, during the late 1990s, the “New Economy” of Clinton’s second administration boomed, the architects of its economic policies took victory laps. Good times were short-lived, however. Soon, globalization gutted many regions. The coasts and the cities left much of the rest of the country behind. Inequality grew. There has been little social mobility. The Bush and Obama years stayed the course, carrying forth a Clinton-era liberalism that benefited American elites almost entirely alone.
Only in the backwash of this failure does DeSantis’s politics, in which he trolls the delusions of a liberal elite establishment that has not yet faced up to these facts, make sense.
In hindsight, our mid-1990s admission to Yale was our opportunity to join this elite. Every member of the team was handed that same ticket. Some of us punched it, in different ways—becoming bankers, consultants, writers, and doctors. Others threw it away, returning home to lives for which a Yale degree was not necessary. I punched it, remaining in elite academia where I have spent all my adult life. D now eyes the presidency by running against everything he says the Yale of our youth represents.
LIKE ALL POLITICIANS’ MEMOIRS, The Courage to Be Free begins with childhood. But we learn few intimate details about DeSantis’s family and upbringing. Most of the first chapter recounts his youth baseball team’s trip to the Little League World Series, where he learned that “hard work can pay off.” It’s only Little League, but this is the first taste of DeSantis’s ambition, his unrelenting theme. A few pages later and DeSantis is heading off to Yale.
Only now does the narrative break, and DeSantis flashes back to tell the story of his family’s origins, contrasting it to the “wealthy” families that typically sent their children off to the Ivy League. DeSantis was raised in Dunedin, an unremarkable community on the west coast of Florida. His father, however, grew up in “steel country, in a town called Aliquippa, about twenty miles northeast of Pittsburgh.” His mother hailed from a similar “blue-collar, working-class area” in Ohio. So would his eventual wife.
DeSantis’s paternal grandfather worked for the Jones & Laughlin Steel Corporation’s Aliquippa Works, when it was built “the largest steel mill in the world.” He says that “[p]art of the reason Yale represented such a serious culture shock” was that, in addition to his Florida upbringing, his “other frame of reference” was his family’s “working-class” roots in steel communities. These company towns first formed of late 19th-century Southern and Eastern European immigrants. DeSantis’s heritage is Italian.
Quite rightly, DeSantis alludes to the decimation of these communities in the 1970s and 1980s, when “production shifted to China and other low-cost countries.” Jones & Laughlin shuttered the Aliquippa Works in 1984. The factory closure “gutted the community, and the population of Aliquippa hemorrhaged to twelve thousand by 2000.” In 1982, DeSantis and his family joined the substantial migration of the children of Midwestern industrial working-class parents south for the new economic opportunities of Sun Belt states like Florida.
Will Dickey/The Florida Times-Union via AP
Ron DeSantis with his family on Election Day, November 6, 2018, in Ponte Vedra Beach, Florida
In Florida, DeSantis’s father installed devices for Nielsen’s television ratings company. His mother was a nurse. At Yale, several teammates hailed from wealthy East Coast families. Far more were children of middle-class families from across the country. This became a demographic function of Ivy League sports at that time, to widen the school’s geographical footprint, which, inevitably, expanded its class footprint.
In 1990, my sense is that most Yale baseball players were from the East Coast. By 2000, most were not. Some were from quite humble financial backgrounds. Somehow, it was their sensibility that our entire team inhabited. We cultivated our own faux class consciousness by setting ourselves up against the most privileged students at Yale, who, in truth, we did not actually know very well given just how much we isolated ourselves from the rest of the student body. This made it easy for D to fall in with us. We could only have sharpened whatever sense of class difference he felt upon his arrival to campus.
We assumed these more privileged students likely attended fancy New York City prep schools, or New England boarding schools. Probably, their parents went to Yale, too. They seemed to arrive as freshmen with heroic levels of academic preparation, compared to those of us who went to public school in Texas, as I did, or in Florida, like D. They had a different social preparation, too. Yale, it seemed, existed for them to have a good time. We all had to mix a bit, in the dorms and dining halls. But for these kids, we imagined it meant slumming it for a time, before returning to Park Avenue.
We despised these real and imagined classmates. We could be mean to them, sometimes very mean—especially if they were women. We stuck to our own, forming alliances for the sake of partying and sex with like-minded men’s and women’s teams. We found other ways, symbolically, to separate ourselves. One way was employment. Financial aid existed, but was nowhere near as generous as it is today. To make ends meet, DeSantis did odd jobs. He “even,” as he writes, “worked as one of the ball boys for Yale soccer matches—when the ball went out-of-bounds, I would run to retrieve it and give it back.” I did that work, too. Unlike D, I confess, I did not really need that money, given my family’s finances. But taking these jobs distinguished me, to myself at least, from the even more wealthy students.
And yet we were all, to various degrees, seduced by Yale. Seduced, that is, by the idea that because of our admission, somehow, we were anointed and special. Yale inculcated in us a general sense of possibility for our lives that we had not expected to have. It made us gutsier.
D was among the most touched by this stirring force, which showed up in different ways. Rarely on our team did it present as academic hustle and drive, but it did for D, and for me, too. We took many classes together, quietly enjoying our ability to outperform the prep school kids. They couldn’t last a second on the baseball diamond with us. We could beat them in the classroom, too.
Refusing to embrace his identity as a meritocrat, DeSantis fashions himself as a populist who speaks on behalf of “the people.”
Ultimately, however, the horizon was narrow. A Yale degree opened toward professional degrees—law school and medical school, basically (I zagged and got a Ph.D.)—or jobs on Wall Street. We knew some Yale kids might head to New York City, to work in arts and culture, but baseball players did not do that. Wall Street was not just a career but a social world, their world, the one we told ourselves we hated.
It felt like the choice was to reject this world or be fully absorbed by and into it. At the end of the 20th century, Yale—opening its doors to students like us from all corners of the country, some of us poor—did not itself transform. Yale transformed you. Or you walked away from it, after four years. Some wanted it both ways, to have a Yale-charged life but to still somehow reject Yale elitism. This is what DeSantis is still doing: trying to reach the elite pinnacle of the American political establishment, while railing against that same establishment.
By this, I do not mean DeSantis is a hypocrite for criticizing the upper-crust university that molded him—at least, no more than anyone else who went to a good college, enjoys its benefits, but still thinks something is wrong with the country. Rather, I mean DeSantis seems stuck. His political persona is one forged around the desire to be at once an insider and an outsider—of the fantasy really, of getting something you want for your personal identity (the privileges of Yale) without having to give something else up (roots back home). I recognize this conflict, because I lived it, and saw it play out at Yale so often among our set.
Since graduation more than two decades ago, most of us have outgrown the conflict. DeSantis appears still positively consumed by it. He is not a man at peace. He is agitated. The conflict has possessed him. Refusing to embrace his identity as a meritocrat, DeSantis fashions himself as a populist who speaks on behalf of “the people.” But that is not an easy thing to do in 2023 when the dissatisfactions of Clinton-era elite class formation are still ringing in your ears.
WHAT HAS CARRIED DESANTIS TO THE NATIONAL POLITICAL STAGE has been, indeed, his Yale-charged ambition, but also his sincere contempt for liberal elites. That contempt is politically motivated. But it is also marked by DeSantis’s determined intelligence, which bears the mark of the same academic standout I once knew at Yale. It is even courageous—which is more than can be said for much of the Republican Party. All of this explains why DeSantis distinguished himself on a series of national political issues in preparation for jumping into the race for the Republican nomination.
DeSantis first appeared on the national political stage after Trump’s election in 2016. A Florida congressman elected in 2012, he became one of Trump’s most vocal supporters, especially on Fox News, when after the election many of Trump’s opponents in Washington alleged that his campaign had conspired with Putin’s Russia. This was precisely the kind of issue that DeSantis could exploit.
The Clinton-cum-Obama-cum-Clinton wing of the Democratic Party’s obsessive focus on Russia in the aftermath of Trump’s election dodged the rot at the heart of public life that had given rise to him, as it alienated so many Americans from the Democratic and Republican Parties alike. In shock, they refused to take stock of the last 20 years and instead took flight in embarrassing speculations that Putin was really occupying the White House. DeSantis’s political gambit became, essentially, to appear on Fox News and rub their faces in it, and that way to appeal to Trump’s supporters—and even the man himself.
In 2018, DeSantis decided to run for the Florida governorship. The only way to have won, he admits, was to have earned “an endorsement from President Donald Trump.” DeSantis asked Trump for his endorsement, and received it, when Trump tweeted, “Congressman Ron DeSantis is a brilliant young leader, Yale and then Harvard Law, who would make a GREAT Governor of Florida. He loves our Country and is a true FIGHTER!”
After Yale, DeSantis attended Harvard Law School. In his memoir, DeSantis admits his “heart” was never in law school. He did not fit in with the crowd. Most Harvard Law School graduates seek, as DeSantis puts it, “a lucrative career in business or law.” DeSantis did not. He became a lawyer in the Navy JAG Corps. In the wake of 9/11, he “wanted to serve.” But soon after his return from Iraq, DeSantis left the Navy and entered the local Florida political scene. In Washington, DeSantis did not fit in, either. He did not make friends with the “DC Republican establishment.” In 2015, DeSantis joined the right-wing Freedom Caucus. In 2016, he fell in line with Trump quickly. But he often “felt like I was spinning my wheels”—one of his favorite expressions—as a congressman.
Trump’s 2018 endorsement vaulted DeSantis into the general election for the Florida governorship, where he faced off against the Democratic candidate Andrew Gillum. In a close race, DeSantis won. Finally, the stage fit. He was “in the big leagues now.”
DeSantis took being governor seriously. He studied the powers of his office carefully, looking for every point of “leverage” he could find to affect his agenda. After only two years in office came the COVID-19 pandemic.
DeSantis’s response to COVID as governor of Florida launched his career as a national politician. To some right-wing Republicans, this is vital. It distinguishes him from Trump, who as president, DeSantis suggests, fell prey himself to “Faucism.” DeSantis begins this chapter quoting Dwight D. Eisenhower’s Farewell Address, when the general warned that “we must … be alert to the … danger that public policy could itself become the captive of a scientific-technological elite.” Eisenhower deserves credit for his “admonition about the dangers of turning over the country to the likes of Dr. Anthony Fauci.”
Brynn Anderson/AP Photo
As Florida governor, Ron DeSantis tours the state’s Bureau of Public Health Laboratories, where the COVID-19 virus was being tested, March 2, 2020, in Miami.
DeSantis’s criticisms of “Faucism” are debatable, but in no way unintelligent or uniformed. To him, it was misguided to insist on mass lockdowns to eradicate COVID. The problem was with the models. In March 2020, DeSantis writes, “governors were receiving different epidemiological models concerning hospital capacity in each of our states. Most of these models forecasted far more patients being hospitalized for coronavirus than the total bed capacity in the state—usually by an order of magnitude.” Heeding the models, the federal government announced on March 16, 2020, the first 15-day lockdown to “stop the spread.”
“I did not know if the models were accurate,” DeSantis reflects, “but I also recognized that there did exist a degree of uncertainty in those early days of the pandemic, including about hospitalization peaks.” Unlike the boastful governor of New York, DeSantis had the good sense to sign a government order forbidding the release of COVID-positive individuals back to nursing homes.
Then Trump held a press conference on March 29, 2020, with Fauci behind him, expanding the 15-day lockdown to 30 days. Congress passed the $2.2 trillion CARES Act, to finance the shutdown with unemployment benefits and forgiving loans. When Trump ceded authority to Fauci, “[w]hat started as a precautionary fifteen-day period of social distancing had transformed into a de facto shutdown until eradication.”
DeSantis says he did not trust Fauci because he had done his own homework. This was a remarkably brazen act of intellectual self-confidence by the former straight A student at Yale. “I decided that I needed to read the emerging research and consume the available data myself …” In particular, he read a lot of “pre-COVID pandemic guidance,” including CDC guidelines (for influenza outbreaks), which “frankly acknowledged the limited effectiveness of ‘mitigation’ strategies.” From this literature, DeSantis decided that the initial 15-day lockdown was warranted, but not the subsequent federal and state-level lockdowns.
DeSantis’s criticisms of “Faucism” are debatable, but in no way unintelligent or uniformed.
By the end of April 2020, “it became clear that the epidemiological models predicting catastrophic collapse of the hospital system were grossly inaccurate.” Early models predicted New York City would need 140,000 beds for COVID patients. Hospitalization peaked at 18,000. It became evident to DeSantis, studying countries like Sweden that did not lock down, that waves of COVID infection featured “about a six-to-eight-week period during which the wave could escalate, peak, and then decline.” How much “mitigations” affected the waves was not obvious. We did not (and still do not) know very much. Because of the uncertainty, DeSantis leaned toward upholding the “normal functioning of society.”
DeSantis chose to keep Florida as open as possible. “As the iron curtain of Faucism descended across our continent, the State of Florida stood resolutely in the way.” For the “US expert class,” DeSantis writes, any “discussion of the harms imposed by their mitigation delusions was akin to advocating for mass murder.” Florida became “the number one target of media attacks for virtually the entire pandemic—for keeping our beaches open, protecting the operation of our businesses, requiring in-person education for grades K to 12, and for not imposing a statewide mask mandate.”
In hindsight, I think DeSantis was right to keep Florida open. Or, at minimum, it is not clear that he was wrong. Excess mortality statistics in Florida do not look much different than elsewhere. Many school closures, which disadvantaged the most already disadvantaged children, today look highly questionable.
Perhaps DeSantis and Florida just got lucky. Lucky or not, due to his inherent mistrust of “liberal elites” and faith in his own intellectual capacities, DeSantis got much of the pandemic response right. Having aced Yale and Harvard gave him the intellectual training and confidence to reject Ivy League–stamped epidemiological models and liberal-establishment pandemic sensibilities—not out of hand, but after close study. At this singular moment, DeSantis was the insider who was not too inside, but the outsider who was not too outside. The seeming equipoise did not hold for long.
IN THE LAST CHAPTERS OF DESANTIS’S MEMOIR, COVID recedes into the background. Clearly, DeSantis begins to seek out the national political headlines by taking inflammatory positions in the culture wars. He lashes out against “woke capitalism,” recounting his effort to remove Disney’s subsidy in the state of Florida after the corporation objects to provisions of Florida’s “Parental Rights in Education” bill, which prohibits schoolroom discussions of sexual orientation and gender identity prior to the third grade. He begins to wage trench warfare against the Florida state university system.
The Courage to Be Free concludes with a scornful chapter, in which DeSantis lambastes concentrations of political and economic power in Washington, woke publicly traded corporations, Big Tech, the ESG movement, the corporate legacy media, the “Fauci-worshipping coastal elites,” university professors, and the ruling, establishment expert class more generally. Presidential candidate DeSantis is running against all of it and all of them. He promises to always pursue “policies that defy the leftist ideology of the nation’s elites.”
“The leftist ideology of the nation’s elites” is a rather esoteric political target. You almost need a Yale degree to even know how to caricature it as deftly as DeSantis does. Doing so makes for a strange comedown in The Courage to Be Free, after the chapters on COVID, which was, after all, a most serious matter of life and death. Perhaps COVID is now old news, the trauma of it fading too fast from memory to be a decisive political issue in 2024. Regardless, the issues that DeSantis has recently latched onto, whether bathrooms, critical race theory, or Disney’s Florida tax status, are not so serious. It is not clear they matter all that much to voters. Why do they matter so much to D?
Trump first ran on an issue that did matter, immigration. Today, he runs on his personality alone, brazenly being himself, positively knowing who he is. Trump lives in the historical moment, which may well—we still don’t know quite yet—prove to belong to him. Campaigning against “leftist ideology” means DeSantis’s agenda must be, essentially, a negative one. Running against Yale, DeSantis runs against a part of himself—a part forged during an era of American past, the 1990s, that now belongs to the dustbin of history. It was none other than Bill Clinton—from a poor Southern background and Yale-educated just like DeSantis, but comfortable in his meritocratic skin—who always liked to say that campaigns are about the future, not about the past.
In the present, DeSantis’s campaign is struggling, even if it is far from over. Still, the idea among some Republicans that there could have been a candidate who could appeal just enough to Trump’s populist supporters without being Trump himself, while still appealing just enough to decorous-minded Republicans who oppose Trump, was a fantasy. For DeSantis, it is a fantasy first given life by a schoolboy wearing a T-shirt and jean shorts on a baseball diamond, many years ago.
