The World v. Alan Dershowitz

Alan Dershowitz, photographed in his New York City home last month. / Portrait by Chris Buck

Alan Dershowitz is the author of 35 books, and by his count, at least the second-most-published lawyer in the universe. As a cable-news fixture, as a legal advocate for celebrities in deep criminal shit, he has again and again propelled himself into the nation’s collective field of vision like some kind of fame-seeking dirigible. (There’s an old joke about a TV camera and Alan Dershowitz and it being imprudent to position oneself between the two.) The first time we meet, though, he doesn’t seem eager for exposure.

It is evening in mid-September and a thunderstorm has recently cleared up over the Upper East Side of Manhattan. Dershowitz is at the 92nd Street Y talking with Jeffrey Toobin, his former Harvard Law School student and fellow pop jurist. Dersh, the onetime possessor of an iconic ’fro, has at 78 years old settled for a more cropped look. Tonight, like Toobin, he is wearing a dark suit and unfortunate laceless slip-ons. The occasion of their conversation is the publication of Toobin’s latest book, a fat tome on the saga of heiress and kidnapee Patty Hearst, one of Dershowitz’s former clients. Audience questions come in written form and steer the subject away from Hearst toward Dershowitz.

“This is a question I’ve never been asked before,” Dershowitz deadpans, peering down at a stack of index cards.

“Knowing you have a guilty client who committed a heinous crime, how do you deal with defending and getting an acquittal for such a client?”

“Enough about O.J., okay?” chimes Toobin, to audience titters. It is the season for O.J. nostalgia, as multiple multipart television events have retraced Simpson’s double-murder trial—and, to an extent, Dershowitz’s role on his defense team. But Dershowitz, who relishes moralistic grillings, takes the question at face value.

“The reason I defend the guilty is because I want to make sure there are very few innocent who are ever charged,” he says evenly. “The vast majority of people charged with crimes are guilty, thank God for that. We wouldn’t want to live in a country where the majority of people charged with crimes were innocent.” With that out of the way, Dershowitz indulges the crowd and retraces the disputed provenance of the blood splotches on O.J. Simpson’s sock.

After the program ends, the two men repair to the lobby, where Toobin signs copies of the Hearst book and Dershowitz sits at an adjacent table signing copies of his latest, a slim political treatise called Electile Dysfunction that he dashed off longhand over the summer in Martha’s Vineyard. The line for autographed copies of Electile Dysfunction dissipates quite a bit sooner than Toobin’s line, so I walk up to the emeritus law professor and say hello. Dershowitz, who had texted me that morning that he was “traveling,” blanches and informs me he has to take off for Virginia the very next morning, and should probably be getting home. I acknowledge that the last time we spoke, in the spring, he had expressed reticence about submitting to a magazine profile. Dershowitz nods as he begins to shuffle away. “There’s still reticence.”

Alan Morton Dershowitz is not, as a rule, reticent. The point of his most famous book, Chutzpah, was to admonish fellow Jews for their reticence. Besides, the guy was on with Megyn Kelly the night before, plugging Electile Dysfunction and cracking “arousal” jokes about his support for Hillary Clinton. Lately, though, he’s had reason to proceed with caution. For the past two years, Dershowitz’s highest-profile case has been his own.

In late 2014, a woman named Virginia Roberts alleged in court that financier and convicted sex offender Jeffrey Epstein had kept her as an underage sex slave, while arranging for various high-profile friends—including Dershowitz—to sleep with her. Dershowitz himself wasn’t sued and was never charged with anything, but nevertheless went ballistic, denying the accusation vigorously. What followed was an almost absurdly rancorous prizefight between Dershowitz’s and Roberts’s high-profile lawyers. They sued him for defamation. He shot back with claims of an extortion plot. Both sides dug in.

The legal warfare has come at a fraught time for Dershowitz. Since retiring from Harvard at the end of 2013, he has been fighting a different, ideological battle. The recent trend in left-wing activism has been to tackle power imbalances among different identity groups. Black Lives Matter has become the dominant social protest movement of its generation. Reports of campus sexual assaults have skyrocketed. Meanwhile, the rhetoric behind the new progressivism can seem at once militant and ultrasensitive, as intent on shouting down injustice as policing hurtful words.

Much of this horrifies Dershowitz, who sees in the movement left-wing intolerance and speech-chilling political correctness. He has responded—in op-eds, on cable news—with stridency. “He’s upset by it, panicked by it, sees the implications for the future,” says his friend and collaborator Harvey Silverglate, a Cambridge civil liberties lawyer. And the implications for his legacy. The identity politics he bemoans, with its focus on various forms of entrenched privilege, does not look kindly on old white guys prone to burping out politically incorrect broadsides. Especially not when they’ve been accused of sleeping with an underage sex slave.

After considerable back-and-forth—there is always back-and-forth with Dershowitz—he eventually agrees to speak with me, at length. I accompany him to taped media appearances. We drive around his old Brooklyn neighborhood. He explains to me that in the end he’d rather try to clear his name in public than play it safe. Despite the cases having been resolved, he is, he says, the elusive innocent victim. “I’m not satisfied with the case just dying,” he says. “There are still people who believe it. I have to persuade everyone that there is nothing to this, that it’s a frame-up. And I won’t rest until I’ve done that.”

In an immediate sense, Dershowitz is fighting to make sure his New York Times obituary doesn’t contain the words “Jeffrey Epstein.” But it’s a mistake to see this latest bout of truculence as a one-off. Dershowitz feels under siege, not just from his accuser, or her superstar lawyers, but also from a whole constellation of contemporary norms. In a political moment suffused with status anxiety—much of it the white male variety that carried Donald Trump to the presidency—Dershowitz, too, seems eager to reassert his place in the world. So he’s reverted to doing what he does best: getting the last word.

In a way, it started with the skin flicks. In 1969, Boston’s Symphony Cinema, long since defunct, attempted to screen I Am Curious (Yellow), a Swedish movie banned by the state of Massachusetts. The film was disturbing, pretentious, and a critical failure. But it generated infamy for a scene in which a woman kissed a man’s limp penis. Boston police seized the reel, and suddenly everyone wanted to watch. Enter Alan Dershowitz. At 30 years old and already the youngest tenured professor in the history of Harvard Law School, he was hired to represent the distributor. The prodigy had scant courtroom experience, but successfully convinced a federal court to lift the ban. I Am Curious (Yellow) would go on to become the top-grossing foreign film in America.

Fast-forward to 1975. By the time Dershowitz represented Deep Throat star Harry Reems, who was appealing a conviction on an obscenity charge—merely for appearing in the hit porno—Dershowitz had become the free-speech lawyer of record. Dershowitz’s porn period wasn’t just a porn period. The two cases bookended his evolution from wunderkind scholar to megawatt lawyer and public intellectual. Dershowitz was a free-speech fetishist and an at-all-costs opponent of government censorship, establishing him during the secretive era of the Pentagon Papers and the Watergate scandal as a folk hero in his own right. Thanks to his growing renown, Dershowitz also exerted his First Amendment right to never again be quiet. He scored standing gigs on proto-shoutfests such as Firing Line and The Advocates. He wrote a monthly column for Penthouse. He’d pop up in places so obscure it was hard to accuse him of being a standard-issue attention hound. “He used to appear on Soviet TV back in the days of the USSR,” recalls Boston Globe columnist Alex Beam. “To be fair to him, he’s never eschewed small-bandwidth publicity vehicles.”

Soon, media saturation became a legal strategy, too. He seemed to spend as much time spinning his cases to the press as he did trying them. “What he taught me in all of my cases is you’ve got to pay attention both to what’s happening inside the courtroom and outside the courtroom,” says his former research assistant Susan Estrich, who recently represented ousted Fox News chief Roger Ailes in his sexual harassment case. “Alan’s message was always, ‘Don’t be afraid.’ Too many lawyers are afraid to talk to the press, lest they say one word wrong.”