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Throughout the late 1960s, the justices of the Supreme Court spent at least one day each year in the basement watching porn together. By all accounts, it was fantastically awkward. Unable to define “obscenity,” but convinced that the First Amendment couldn’t protect unduly dangerous and morally corrupting expression, the Court was forced to create constitutional law one sex-scene at a time.

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These films ranged from scientific documentaries to the improbable escapades of lesbian nymphomaniacs. Justice Thurgood Marshall, a civil rights hero, took merciless pleasure in narrating the clips for the special benefit of Justice John Marshall Harlan Jr., an elegant former Wall Street lawyer who was by then losing his eyesight. Mocking Justice Potter Stewart’s insistence that “I know it when I see it,” clerks would call out in the dark, “I see it, I see it!” In 1968, some 20 years after serving in the U.S. Navy, a still-youthful Stewart reflected on more adventurous times and confided in a particularly curious clerk that he had indeed seen it, “Just once, off the coast of Algiers.” (I assume you can guess who that curious law clerk was.)

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For years, the justices struggled to explain what made frank depictions and descriptions of sex dangerous. What was so harmful about obscenity? At what point, or with what body part, did a book or film land outside the First Amendment? The Court’s logic fluctuated wildly from case to case. Such instability is uniquely troubling for free speech because too much uncertainty about the limits of the criminal law can chill innocent expression.

The 1960s was not an isolated period of doctrinal confusion. As Uncertain Justice explains, since the 1790s, Americans have struggled — sometimes successfully, other times not so much — to reconcile free speech with competing values and fears. Our history is rife with examples of legally-sanctioned suppression, particularly before the 1940s, and the seemingly absolute text of the First Amendment has long been understood to raise more questions than it answers. The Court’s efforts to implement the First Amendment as law have always inspired strong feelings and a measure of uncertainty.

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Nonetheless, conventional wisdom tells us that we now live in a time of stable, certain protection. Floyd Abrams, a rightly celebrated First Amendment attorney, thus explains that “it is unpopular speech, distasteful speech, that most requires First Amendment protection, and on that score, no prior Supreme Court has been as protective as this.” Rarely does an American stand silent, or speak in whispers, for fear of punishment. Liberty reigns supreme. Or so the story goes.

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This picture obscures more than it reveals. So does the picture that claims the justices pretty much protect the speech with which they personally agree. In the 1960s, the Court failed because it couldn’t reliably define the First Amendment’s limits. Today, the Roberts Court risks a different kind of misstep: creating doctrine that simply doesn’t cohere.

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In one significant line of cases involving vulnerable speakers, the Court has displayed a striking taste for flexibility while creating new gaps in the First Amendment’s canvass. To take a few examples, it has stripped many protections away from students speaking about drugs (Morse v. Frederick), human rights activists training terrorist groups to use peaceful conflict resolution in lieu of violence (Holder v. Humanitarian Law Project), prisoners locked in brutal isolation units (Beard v. Banks), and public employees keen to speak about official (mis)conduct (Garcetti v. Ceballos). This Court has also weakened protections for discussion about exchanging child porn, for public protests, and against retaliatory arrests. Each time, the Court prioritized values other than liberty and emphasized that the identity of the speaker or context of the speech diminished the First Amendment’s role.

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Humanitarian Law Project, for instance, displayed stunningly broad deference to the Executive Branch regarding the danger posed by human rights activists who wish to help terrorist groups pursue entirely peaceful goals. In that case, the Court required only a dash of “informed judgment” by the executive that such “support” is “fungible” and can thus indirectly aid terrorist activities. (Notably, Roberts, HLP’s author, wrote a First Amendment decision just a few years later rejecting a similar government claim about resources being fungible.)

In Beard, the Court saw no problem with prison officials treating speech rights as bargaining chips to incentivize good behavior in isolation cells. It adhered to that view even though hardly any evidence proved the merits of transforming First Amendment freedoms into an elaborate psychology experiment, and even though inmates’ rights to read, receive, and think were all squarely at issue. (Breyer, who wrote a powerful dissent in HLP calling for careful scrutiny of the empirical basis for congressional limits on speech, wrote the majority in Beard and happily deferred to even less informed speculation by corrections staff).

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And in Garcetti, a case about public employee speech rights, the Court created an odd distinction focused on the capacity in which employees speak (as “employees” or “citizens”), bluntly throwing transparency, public accountability, and employee speech rights under the bus in favor of greater government efficiency. (At oral argument this Term in Lane v. Franks, the Court seemed to recognize the need to walk back some of Garcetti’s more incautious reasoning.)

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These and other speech-restrictive cases reveal a very different face of the Roberts Court — a face that scowls on certain kinds of speech claims — and such cases have rightly drawn critical attention from legal scholars. National security, order in schools, speculative penology, law enforcement objectives, and smooth government process all have trumped liberty.

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In contrast, the Robert’s Court pro-speech reputation mostly comes from a series of high-profile rulings about obviously hateful speech: animal crush videos (United States v. Stevens), brutally violent interactive video games sold to kids without parental consent (Brown v. Entertainment Merchants Association), bigoted military funeral protestors (Snyder v. Phelps), and false claims to possess the Medal of Honor (United States v. Alvarez).

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In this line of cases, the Court has repeatedly insisted in sweeping terms that rigid, history-based rules are necessary to save speech from tyranny. Thus, while upholding borderline speech claims that involve significant social harms and barely implicate concerns of political censorship, the Court has condemned just the sort of common law interest-balancing that manifestly animates what it has actually done in HLP, Beard, Morse, and Garcetti. In a booming voice, the Court has declared itself scandalized — scandalized! — by the notion that courts can be trusted to play a role in reshaping First Amendment rights. And then it has still gone on to play that very role in opaque and insufficiently explained ways.

As demonstrated by a series of cases decided between 2010 and 2012, Kagan has played an especially intriguing role in this story.

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In 2010, as solicitor general, she argued in Stevens that depictions of illegal animal cruelty should be deemed totally unprotected by the First Amendment. She urged the Court to reach that result by holding that “whether a given category of speech enjoys First Amendment protection depends upon a categorical balancing of the value of the speech against its societal costs.” In a cold and uncompromising opinion for eight justices, Roberts rejected as “startling and dangerous” Kagan’s proposed “free-floating test for First Amendment coverage.” He declared that history and history alone defines which kinds of speech are not protected (or less than fully protected) by the First Amendment. That list, he added, is basically closed, and the Court would not re-open it to include animal cruelty.

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In 2011, newly installed on the Court, Kagan provided Scalia with the crucial fifth vote in Brown, the violent video games case, for an opinion that decisively rejected the views she had espoused in Stevens as solicitor general. Indeed, Scalia’s opinion striking down California’s regulation of the sale of violent video games to minors without parental consent borrowed heavily from the Chief’s ringing declaration in Stevens: although the sale of obscenity to kids has long been regulated, quite the opposite is true of violent literature, music, and comic books (just consider Hansel & Gretel!). Because of this historic tradition, Scalia declared, the sale of gruesome videogames to minors had to be fully protected. California’s law thus faced and flunked strict scrutiny. To explain this seeming inconsistency in her free speech commitments, perhaps Kagan would borrow Justice (and former Attorney General) Robert Jackson’s famous remark that “the matter does not appear to me now as it appears to have appeared to me then.”

But even if she did that, she’d have more to explain. Just one year later, in Alvarez, Kagan pointedly deprived Kennedy of a fifth vote for a Stevens/Brown-like opinion holding that lies about possessing military medals are fully protected as free speech. Instead, she joined a concurrence by Breyer in which he argued, in an echo of Kagan’s Stevens position, that the “Stolen Valor Act” should be tested to see “whether [it] works speech-related harm that is out of proportion to its justification.” On this view, which is diametrically opposed to that of Roberts and Scalia, judicial balancing of First Amendment interests is crucial to achieving the right result.

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Kagan’s seemingly irreconcilable votes are only part of the fascinating tale of this Court’s pro-speech rulings. Even as Roberts, Kennedy, and Scalia have written broad opinions looking only to history-based categories of “protected” speech, their colleagues have resisted that approach at every turn. Alito has produced devastating critiques of Scalia’s originalist methods. Thomas has out-flanked Scalia by devising imaginative and speech-restrictive originalist opinions. And Breyer has repeatedly urged the Court to consider values that compete with or at least greatly complicate values of liberty. Ginsburg and Sotomayor have joined the pro-speech majority every time, but not once have they written separately to explain their views.

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These cases, moreover, have sometimes shielded speech for reasons that may feel hard to accept. As Breyer asked in Brown, for instance, “What kind of First Amendment would permit the government to protect children by restricting sales of [an] extremely violent video game only when the woman — bound, gagged, tortured, and killed — is also topless?” Or consider Snyder, the case about homophobes who showed up at military funerals to denigrate our fallen soldiers and condemn our nation for finally opening military service to gay men and lesbians. There, the Court protected the protestors for a reason (namely, that they spoke about a matter of public concern) that had nothing to do with why the bigots otherwise could be punished (namely, that they intentionally inflicted devastating emotional pain on the dead soldier’s father).

At the very least, the Court’s deeply conflicted pro-speech rulings remind us that liberty can come at a heavy price — and that the rules we devise to protect it are rightly subject to an evolutionary dialogue between courts and the rest of society.

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In Chapter 4 of Uncertain Justice, Joshua and I explore in detail this Court’s fascinating, tortured relationship with the First Amendment. We offer an overview of all the leading cases, draw out striking patterns of coherence and contradiction, and demonstrate that there is much more to this Court’s engagement with freedom of speech than meets the eye. In the end, our goal is to explain where this Court may take us, why its ruling have so often broken down along unexpected lines, and what the remarkable differences between the justices tell us more broadly about the future of the Roberts Court and its impact on how we live.