Think of the American Civil Liberties Union during the last two decades of the 20th century, and a certain type of person invariably comes to mind: shrewd, thick-skinned, and possessed of an unwavering—some might say irritating—commitment to principle. The men and women of the ACLU were liberals in the most honorable, but increasingly obsolescent, meaning of the term. They understood that the measure of democracy lies in the impartial application of its laws, and were prepared to defend anyone whose constitutional rights were trampled upon, irrespective of their political views or the repercussions that mounting such a defense might entail.The archetypical ACLU figure was also often Jewish, as immortalized in the 2003 Onion story, “ACLU Defends Nazis’ Right to Burn Down ACLU Headquarters.” That joke was based upon the real-life case of National Socialist Party of America v. Village of Skokie, wherein the organization represented a group of neo-Nazis who were denied a permit to march through a Chicago suburb that was home to a significant number of Jewish Holocaust survivors. The image of Jewish ACLU attorneys defending the free speech rights of American neo-Nazis was a source of shame for some Jews but pride for many others, a testament to Jewish confidence in the institutions and values of American liberalism. No American minority had reaped more from its faith in the country’s professed commitment to pluralism and tolerance than the Jews, a gift they repaid many times over by supporting the institutions—the universities, the Democratic Party, the ACLU—which upheld them. In the same way Lenny Bruce classified Ray Charles and fruit salad as Jewish (while claiming that “Evaporated milk is goyish even if the Jews invented it”), so the ACLU was seen as scrappy, authentic, and emblematic of an underdog quality. As Bruce might have put it: the ACLU, Jewish; the McCarthyite American Jewish League Against Communism, goyish.No one embodied that late-20th-century cultural archetype of the fiercely outspoken, intellectual, principled, and Jewish ACLU activist more than Ira Glasser. From his appointment as national executive director in 1978 until his retirement in 2001, Glasser transformed the ACLU from a mom and pop outfit into a “nationwide civil liberties powerhouse,” broadening its mandate to include issues such as sexual orientation discrimination and abortion rights. Through his ubiquitous and spirited media appearances, Glasser became the face of civil liberties in America. When Vice President George H.W. Bush campaigned to succeed his boss in 1988—and spoke like a Connecticut blueblood’s idea of a Texas hayseed—he derided his opponent Michael Dukakis as a “card-carrying member of the ACLU.” It was guys like Glasser whom Bush was trying to conjure up in the minds of the voting public.Mighty Ira, an admiring new documentary about Glasser’s life and times, opens with a visit by its octogenarian namesake to the site of a Brooklyn sports stadium that no longer exists, where a team that skipped town over six decades ago used to play. Standing on the former grounds of Ebbets Field, atop which a massive housing complex now stands, Glasser speaks of the former baseball grounds as a “shrine,” and the 1947 Brooklyn Dodgers starting lineup with religious awe. His first visit as a 9-year-old fan coincided with the Dodgers signing Jackie Robinson, and rooting for the team that broke baseball’s color barrier, Glasser asserts, signified more than tribal loyalty to a club, but also faith in “civil rights and civil liberties.”Glasser and his friends rarely encountered anybody who wasn’t Jewish, much less Black, within the 12-block neighborhood of East Flatbush that comprised the world of their childhood (New York City, he says in the film, was less the fabled “melting pot” of popular American sentiment than “a collection of insular segregated tribes”). But while listening to play-by-play announcer Red Barber’s report about the Dodgers’ road trip to St. Louis, then the southernmost city in the National League, they understood two important things: that Jackie Robinson was a god, and that the treatment he endured—the racist invective from Cardinals fans, the segregation that kept him from eating in the same restaurants or sleeping in the same hotels as his teammates—constituted a form of blasphemy.A hatred of Jim Crow and a passion for civil rights developed from Glasser’s dedication to the Dodgers, as did a theory of the nature of sports fandom itself: If rooting for the Dodgers situated one on the right side of what was then the country’s central moral struggle, then cheering for the Yankees (the third to last team to hire a Black player) signified a belief in “oil depletion allowances.” Writing a quarter century after his beloved team abandoned Brooklyn for sunnier Los Angeles and Ebbets was razed to the ground, Glasser observed that “Dodger fans became egalitarians who would often be found working at the ACLU.”Viewers may question the relevance of a documentary about a civil liberties veteran who retired over 20 years ago. The contours of contemporary debates surrounding issues of free speech have evolved as a result of technological advances, demographic changes, the presidency of Donald Trump, and other phenomena too numerous to cite, and a man like Glasser reliving the highlights of his storied career may strike some as indistinguishable from an aging Brooklyn Dodgers fan reminiscing about his long-gone team. The decision by directors Nico Perrino, Chris Maltby, and Aaron Reese to start their film with Glasser waxing nostalgic about Ebbets Field surely risks drawing that conclusion, but what makes this particular trip down memory lane meaningful is its illustration of how dramatically institutions like the ACLU have changed. As much as Mighty Ira is intended as a tribute to an individual life, it cannot help but also be a lament for the endangered values to which that life was dedicated. Ebbets Field may not be the only thing we’ve lost.Glasser’s Brooklyn childhood was largely devoid of adult supervision. Raised in cramped apartments, a rubber Spaldeen ball their only source of after-school entertainment, the Jewish youth of Flatbush “learned how to mediate conflict, handle bullies and disagreements” among themselves, he says. This moral and practical education, on the streets and in the stands of Ebbets Field, prepared him well for a career defending the U.S. Constitution.In 1966, equipped with a graduate degree in mathematics from Ohio State University and restless after a few years editing a small, left-wing magazine called Current, Glasser wrote a letter to his senator, Robert Kennedy, urging him to run for president. Kennedy wrote back inviting Glasser to meet with him in Washington. Addressing the aspiring campaign aide from his chair in the senatorial barbershop, the former attorney general and heir to the Kennedy mantle revealed that he had yet to decide whether to mount a bid for the presidency. Instead, he urged Glasser to take a job he had already been offered as associate director of the New York Civil Liberties Union, the state affiliate of the ACLU.Glasser followed Kennedy’s advice, and for 11 years he broadened the NYCLU’s remit to protect the rights of prisoners, wards of mental institutions, welfare recipients, and other marginalized groups. In 1978, fresh off its successful defense of the Illinois Nazis, the national ACLU tapped Glasser to be its executive director. The organization was in serious trouble, facing a $500,000 budget deficit after losing over a quarter of its membership from a 1973 peak of 230,000. Over the course of his tenure, Glasser not only rescued the ACLU from financial ruin but revitalized it as a bright star in the American liberal firmament, overseeing the group’s expansion from a handful of state affiliates, 35 lawyers, and an annual fundraising yield of $4 million—just enough to cover operating expenses—to one with offices in every state, over 100 lawyers, and an endowment of close to $30 million.It’s long been a cliché that people and institutions—whether politicians, rock bands, or nonprofit organizations—are forced to compromise their integrity as they become more popular. But Mighty Ira makes the point that Glasser improved the ACLU’s stature without sacrificing its foundational principles, which are essentially the country’s foundational principles. The ACLU was created during the post-World War I Red Scare to provide a politically neutral defense of constitutional rights at a time when federal and state governments faced little opposition to their repression of unpopular individuals and groups. For Glasser and his generation of civil liberties activists 50 years later, liberty remained precious, government power was “dangerous,” and the Bill of Rights was necessary to protect the former from the latter.To tell the story of how Glasser did well for the ACLU by doing good for the cause of free speech, the filmmakers use footage of their subject making the civil-libertarian case across a range of TV talk shows and public forums throughout the 1980s and ’90s. The most memorable of these appearances was on Firing Line, the legendary public debate program hosted by conservative eminence William F. Buckley Jr. Though their political disagreements were vehement (“Resolved: That the ACLU is Full of Baloney” was the topic of one debate), and they came from radically different socioeconomic backgrounds, Buckley and Glasser managed to find common ground in their shared opposition to the government’s war on drugs. Their unlikely rapport embodied something increasingly rare, another relic from the vanishing world of postwar American liberalism: friendship that transcended political differences, even strongly held ones. When the devout Catholic founder of National Review first invited the secular Jewish liberal to lunch at a fancy Italian restaurant, their initial conversation was like “two boxers trying to figure each other out,” Glasser told me in an interview late last year by phone from New York City. “I think we intrigued each other. I was this street kid from Brooklyn, my father was a construction worker, labor union guy, and I think [Buckley] was sort of surprised and intrigued that somebody with my background could contest with someone like him as successfully as I did.”Not that they ever pulled punches. Debating the constitutionality of flag burning on Firing Line, Buckley told Glasser something to the effect that the “average American” has a visceral reaction to the desecration of the Stars and Stripes, to which Glasser replied, “Bill, what do you know about the average American? The closest you’ve ever come to an average American is me.” To acquaint Buckley with more such average Americans, Glasser treated him to hot dogs at Nathan’s on Coney Island. (The pair arrived in Buckley’s chauffeur-driven limousine.)Adopting a scrupulously content-neutral approach to the defense of free speech is guaranteed to upset people across the political spectrum, but it was a price Glasser and his colleagues were willing to pay. Religious conservatives like Buckley fumed at the ACLU for arguing on behalf of flag-burners and blasphemous artists, while secular liberals were confounded by its insistence that neo-Nazis had the right to goose-step past the homes of Holocaust survivors. But the defense of the First Amendment was far too important to leave to those concerned with winning popularity contests. Many if not most of the people who dropped their ACLU membership in the wake of Skokie, Glasser surmises, were not longtime members but had joined the group at the height of Watergate just a few years earlier. “They saw the ACLU as effective opposition to Nixon,” and signed up “not because of civil liberties positions but because they were anti-Nixon.”For those whose commitment to civil liberties was primarily if not exclusively a function of partisan politics, the rationale for supporting the ACLU began to fade the minute Tricky Dick delivered his final, awkward wave from the steps of Marine One. By the time the group represented a bunch of brownshirts in the hinterlands of Chicago, whatever vague ideals once moved them to support the ACLU—along with the glamour and sense of self-worth conferred by doing so—evaporated.Then as now, Glasser was at pains to remind the ACLU’s critics that it was not “defending Nazis” in the Skokie affair. It was defending the First Amendment, which remains valid independent of whomever exercises it. Let the government abrogate the free speech rights of one group, however odious, and it will do it again, possibly in the case of someone you like.Almost immediately following Glasser’s July 2001 retirement, however, the organization started to slip. In the wake of the Sept. 11 attacks, a flood of concerned citizens joined the ACLU to oppose the counterterrorism and surveillance policies of President George W. Bush. But when Bush’s suave and eloquent successor continued (or, in the case of drone strikes, dramatically intensified) some of the same measures, many of these new members slunk away from the fight. And unlike the 1970s, when the ACLU was run by stubbornly principled people who refused to buckle under the weight of fashionable opinion or donor pressure, the new generation of leaders prioritized conformism over intellectual consistency.“My successor, and the board of directors that have supported him, have basically tried to transform the organization from a politically neutral, nonpartisan civil liberties organization into a progressive liberal organization,” Glasser says about Anthony Romero, an ex-Ford Foundation executive who continues to serve as the ACLU’s executive director. According to former ACLU national board member Wendy Kaminer in her 2009 book Worst Instincts: Cowardice, Conformity, and the ACLU, Romero and his enablers routinely engaged in the sort of undemocratic and unaccountable behavior practiced by the individuals and institutions the ACLU usually took to court, like withholding information (concerning a breach of ACLU members’ privacy, no less), shredding documents in violation of its own record-preservation and transparency procedures, and attempting to muzzle board members from criticizing the organization publicly. (“You sure that didn’t come out of Dick Cheney’s office?” remarked the late, great former Village Voice columnist and ACLU board member Nat Hentoff of this last gambit). Eerily prescient, Worst Instincts foreshadowed the hypocrisy and fecklessness that has since come to characterize the leadership of so many other, previously liberal institutions confronted by the forces of illiberalism within their own ranks.In 2018, the ACLU spent over$1 million on advertisements likening Supreme Court Justice nominee Brett Kavanaugh to Bill Cosby and Harvey Weinstein, essentially accusing him of crimes for which he was never tried or convicted. More egregious than their brazen political partisanship was the way in which the ads traduced the presumption of innocence, a bedrock of American jurisprudence and a principle the ACLU was founded to uphold. Asked why his organization was willing to further violate its tradition of political neutrality, Faiz Shakir, a Democratic Party operative then serving as the ACLU’s national political director, was brutally honest. “People have funded us and I think they expect a return,” he said. Glasser also points to the group’s decision to run a television advertisement supporting then-Georgia gubernatorial candidate Stacey Abrams as a telling sign of its transformation. “I mean, I love Stacey Abrams,” Glasser told me. “She has become my favorite political character in the country. But the ACLU has always stayed away from that. Nobody attacked Richard Nixon or Ronald Reagan on their civil liberties violations more vigorously and strenuously than I did. But we always stayed away from political partisanship, and it was critical for the ACLU, virtually for all its history, to have standards that were as applicable to those most of us politically supported as to those who most of us politically opposed.”But it is the group’s attitude toward the First Amendment, the ACLU’s bread and butter, that has been most concerning. In 2004, The New York Times revealed that Romero had consented to sign a grant agreement from his former employers at the Ford Foundation, included at the behest of pro-Israel activists, stipulating that any recipient of the foundation’s largesse “agree that your organization will not promote or engage in violence, terrorism, bigotry, or the destruction of any state,” a vaguely worded contravention of free speech principles. Not only did Romero initially refrain from informing the board about the controversial agreement, but he also neglected to mention that he had helped draft it, allegedly recommending the Patriot Act as a model. That same year, the national ACLU was silent about a case involving a San Diego high school student punished for wearing a T-shirt condemning homosexuality, in contrast to the many students it had defended who donned clothing emblazoned with pro-gay messages (or in the case of one Alaska stoner it proudly represented, the message “Bong Hits 4 Jesus”).Of course, no discussion of the ACLU can ignore Donald Trump, whose role in its degeneration, like that of so many other people and institutions opposed to him, was seismic. It was entirely appropriate that the ACLU would be one of Trump’s loudest antagonists; he made violating the letter and spirit of the Constitution an all but explicit plank of his campaign, and his upset victory subsequently led to a dramatic spike in the ACLU’s membership rolls. Accompanying this influx of new members and money, however, were pressures for the group to become another run-of-the-mill #Resistance outfit. In 2017, the ACLU of Virginia had supported the right of white nationalists to rally in Charlottesville. But once the rally turned violent, the national ACLU circulated an internal document with new “case selection guidelines,” stipulating, “Speech that denigrates such [marginalized] groups can inflict serious harms and is intended to and often will impede progress toward equality.” Before agreeing to take a free speech case, the document continued, the ACLU would now consider “the potential effect on marginalized communities,” whether the speech advances the goals of speakers whose “views are contrary to our values,” and the “structural and power inequalities in the community in which the speech will occur.” A manifestation of the ACLU’s new approach can be seen in the decision by one chapter to intervene in a high-profile case at Smith College, where the group amplified bogus claims of racism leveled by a student against some of the school’s custodial and cafeteria staff.Were the ACLU today confronted with a lawsuit similar to National Socialist Party of America v. Village of Skokie, Glasser doubts the group would take it. (Tellingly, in an essay collection celebrating its most important cases published on the occasion of the group’s 100th anniversary last year, the ACLU neglected to include that seminal litigation). And when other constitutional rights have come into conflict with a First Amendment freedom even more unpopular with progressives than speech—that of religion—the ACLU has made it all but official policy to consider claims of religious conscience as smokescreens for discrimination, arguing that an evangelical Christian baker must make cakes for same-sex weddings against his will (a violation of both expressive and religious freedom), and that Catholic hospitals must perform abortions.The embrace of political partisanship, the dropping of standards, the buckling to donor demands at the expense of long-held principles—Glasser says all of these developments have rendered the ACLU unrecognizable from the group he once led. The roots of the ACLU’s evolution from principled, nonpartisan defender of civil liberties into just another cog in the progressive machine are cultural as much as generational. You might say it’s the difference between devotion to the First Amendment and devotion to oil depletion allowances.For instance, whereas Glasser avoided wooing the wealthy, under Romero the group enthusiastically caters to the whims of ultrarich partisan donors whose support for its traditional mission is tenuous. “Glasser and the other ACLU stalwarts of his generation were scrappy and combative, jumping to take unpopular stances at the mere hint of a threat to principle,” reported The New York Times in a 2005 article about the changing nature of the organization and its leadership. Romero, by contrast, was described as having “the diplomacy and charm of a veteran foundation executive,” useful qualities for a courtier to the wealthy but worse than useless for challenging power.This is tragic, for when it comes to free expression, we desperately need leaders with Glasser’s integrity. Practically everywhere one looks, the culture of free speech and intellectual pluralism is under assault, often at the hands of those supposed to cherish it and in spaces where it’s meant to flourish. “Is the First Amendment Obsolete?” asked Tim Wu, a Columbia University Law School professor tapped by President Joe Biden as his senior adviser on technology and competition policy. Last month, Pulitzer Prize-winning New York Times columnist Bret Stephens wrote a piece criticizing the paper’s abysmal treatment of its veteran reporter Donald McNeil Jr.; the column was censored by Times publisher A.G. Sulzberger, and appeared instead in the rival New York Post as if it was samizdat. Two weeks later, a pair of Democratic congresspeople wrote a threatening letter to cable television providers “asking” why they continued to carry the Fox News Channel. More disturbing for the future are the results from the most extensive survey ever conducted of U.S. college student attitudes toward free speech, which found that 60% have withheld an opinion for fear of how a fellow student, professor, or administrator would respond.Fear of speaking becomes more understandable when one considers the increased fervor in support of censorship. The survey, conducted by the Foundation for Individual Rights in Education (FIRE) and which canvassed 20,000 students at 55 of the nation’s top colleges and universities, reports that 60% of self-identified “extreme liberal” students believe it’s acceptable to shout down a controversial speaker on campus, a tactic endorsed by only 15% of “extreme conservative” students. Twenty percent of Ivy Leaguers, meanwhile, favor physically blocking their peers from even hearing a speaker they deem unacceptable, twice the figure among students at non-Ivy League schools.FIRE also discovered that female, LGBT, and Black students are less supportive of free speech than male, straight, Hispanic, Asian, and white students, a worrisome indication that the insidious effort to malign the entire concept of “free speech” as a weapon to “harm” minorities is bearing fruit. Rather than learning how the First Amendment has been a precondition for every social, political, legal, and cultural advancement secured by marginalized groups in America, it would tragically appear that indoctrinating the latter-day beneficiaries of these struggles in the belief that they are helpless against “oppressive structures” and “systems” has convinced many that free speech is their enemy.If the public face of the ACLU was Ira Glasser during the latter part of the previous century, today that honor can be claimed by a staff attorney named Chase Strangio. Named one of the 100 most influential people on the planet by Time magazine last year, Strangio is the ACLU’s deputy director for transgender justice. Like many activists consumed by this issue, he is uncompromising in demanding strict adherence to a set of highly contestable orthodoxies, and merciless toward anyone who dares question them. Two women who have—J.K. Rowling, the author of Harry Potter, and Abigail Shrier, author of a book about the role of “peer contagion” in the rising rate of teenage girls declaring themselves transgender—are “closely aligned with white supremacists in power,” Strangio declared on Twitter, offering not a shred of evidence for this claim. “Stopping the circulation of [Shrier’s] book and these ideas is 100% a hill I will die on,” he wrote, a rather bizarre position for an ACLU employee to endorse. Strangio later deleted the tweet, explaining that his intention was not to call for the government to ban Shrier’s book, but rather “to create the information climate for the market to be more supportive of trans self-determination than the alternative.”Strangio is of course perfectly entitled to his views about the fairness of allowing natal males to compete against natal females in high school sports, and to advocate for an “information climate” suppressing books he doesn’t like. What’s puzzling is why someone with such pro-censorship inclinations would want to work, of all places, at the American Civil Liberties Union. Not to put too fine a point on it, but it’s like a carnivore joining the staff of People for the Ethical Treatment of Animals.Puzzling, that is, until you realize that—like so many other institutions whose worthy missions we naively assumed to be inviolable—the ACLU is no longer itself. The organization known as the ACLU is now led by people beholden to an ideology purporting that the essential function of the Constitution has been to serve as a blueprint for white supremacy, and that its broad free-speech protections are not a tool of emancipation for society’s underdogs but rather the handmaiden of their oppression.The capture of elite institutions by those in thrall to this dogma is how the movie industry can simultaneously venerate victims of the Hollywood blacklist while instituting its own content guidelines in the friendly guise of “representation and inclusion standards.” It’s how you get the bizarre phenomenon of journalists braying for censorship, and a newspaper union abandoning one of its members to the tender mercies of a corporate human resources minion out of Kafka. And it’s how a star attorney at the American Civil Liberties Union, an organization that once prided itself on sending Jewish lawyers to defend the constitutional rights of neo-Nazis, issues a public call for a digital book burning.Another casualty of the new dispensation is the intelligent yet civil debate between ideological adversaries modeled by Buckley and Glasser. For over three decades, Buckley invited the most significant left-wing politicians, activists, poets, intellectuals, comedians, and rabble rousers onto Firing Line. It took confidence to debate a man as well-read and rhetorically ambidextrous as Buckley, but his guests—Glasser prominent among them—gave as good as they got. Watching their spirited conversations, and comparing these with the dreck that fills our television airwaves today, is like an anthropologist discovering a lost tribe. If Buckley were still alive, many of today’s leading progressive heavyweights would not only refuse to debate him; they’d organize a petition to boot him off the air. Some of Glasser’s successors at the ACLU would probably sign it.Much as it tries to inspire hope for the future of free speech and open inquiry, Mighty Ira stands as an elegy to a world that no longer exists—a world in which professional sports teams contributed something actually meaningful to the advancement of racial equality rather than ritualized grandstanding, the most famous conservative in the country was an almost parodically civilized intellectual and not some bloviating demagogue, personal affinity wasn’t contingent upon ideological affinity, and the American Civil Liberties Union stood for principles instead of party. Alas, for the rulers of our brave new world, those principles are as exotic as a Spaldeen ball.