The World v. Alan Dershowitz

The Harvard Law School legend has defended everyone from O.J. Simpson to Claus von Bülow. Now he’s facing his toughest case yet: his own.

alan dershowitz oj simpson

Dershowitz was a member of O.J. Simpson’s legal “dream team” during Simpson’s murder trial. / Photograph via Reuters

Exposure begat more exposure. With each passing year Dershowitz’s notoriety increased alongside that of his clients. In 1983, he argued the appeal for Newport socialite Claus von Bülow, who had been found guilty of attempting to murder his wife, Sunny, with insulin injections. Dershowitz won the case, and wrote a book about the trial, Reversal of Fortune, which became an Academy Award–winning movie (coproduced by Dershowitz’s son Elon). Von Bülow was pissed about his icky portrayal in the film—it was implied that he had once had conjugal relations with his mother’s corpse. But by then, the professor had moved on. There were other celebs—Mike Tyson and Leona Helmsley and Conrad Black and Michael Milken and David Crosby and Jim Bakker—who needed saving. Such was his omnipresence: He was reportedly hired by O.J. Simpson’s defense team to get him to stop appearing on television and hinting at their client’s guilt.

(I’m risking a lengthy letter to the editor, one that will probably come regardless of what I write, if I don’t at this juncture make perfectly clear that Dershowitz has taken a ton of worthy, obscure pro bono cases over the years.)

It was during this era of Dershian ubiquity—from the von Bülow case to the Simpson trial a dozen years later—that public opinion seemed to turn against him. Everybody had a different gripe. In the late 1980s, this magazine staged a kind of journalistic “trial” to investigate his egomania. A few years later, GQ ran a brutal piece arguing that he’d sold his soul for fame and money, while simultaneously cheapening his Jewish heritage by constantly accusing his foes of anti-Semitism. The anti-Semites, for their part, sent him countless pieces of hate mail, mostly to complain that he was appearing on their TV sets at all.

But it’s self-defeating to lament Dershowitz’s desire for publicity. The more one criticizes Dershowitz for pushing his personal brand, the more inclined he is to hop on television and defend himself for doing so. For him, anything less amounts to craven self-censorship—or worse: tribal betrayal. “Notwithstanding the stereotype, we [Jews] are not pushy or assertive enough for our own good,” he wrote in Chutzpah, in 1991. “Despite our apparent success, deep down we see ourselves as second-class citizens—as guests in another person’s land.” Dershowitz’s habit of showing up in your living room came not from a sense of entitlement, but from insecurity.

Which brings us back to present-day New York City, where Dershowitz is hoping to make a few statements for the record.


A couple of weeks after the Toobin talk, Dershowitz invites me to interview him in between other, previously scheduled interviews. It’s a chilly day in Manhattan, where he has lived since his retirement from Harvard. Dershowitz is wearing a Lululemon baseball cap and a dark tie, to mourn the death of former Israeli Prime Minister Shimon Peres, who had passed away the night before. We grab an outdoor table in Bryant Park near the editorial offices of Newsmax, where he keeps a standing TV gig to discuss current events and plug the odd book.

Ideologically, Newsmax is the opposite of state-run Soviet TV, though credibility-wise, the two are about even. Friendly to Israel and suspicious of political correctness in a mainstream, Republican way, the website/cable channel is in some ways a comfortable venue for late-period Dershowitz. Still, he seems anxious that his lower-rent media appearances might lead to misguided generalizations.

“People misunderstand me greatly,” he says, announcing our topic for the afternoon. In person, he’s shyer, more awkward than his public persona would suggest. “I’m seen by some as extreme because sometimes I state my views quite firmly, categorically—particularly on television, where nuance is difficult.” Tinny classical Muzak is emanating from an outdoor speaker somewhere in the vicinity of the New York Public Library. “Some people think I am a radical leftist because of my history of supporting civil rights. Some people think I’m a neofascist person of the right because of my support for Israel. But I’ve always been, even when I was very young, a centrist liberal.”

Dershowitz was raised Orthodox Jewish in Borough Park, Brooklyn, during the 1940s and ’50s. (He hasn’t been strictly observant for decades.) His mother was a bookkeeper and his father ran a shop that sold workmen’s clothing. Alan, then “Avi,” worked his first job tying strings around the ends of hot dogs. Deli grunt was at that point a plausible career path for the woefully underachieving 14-year-old. But he eventually eked his way to Brooklyn College—first in his family to earn a degree—and from there he metamorphosed into a student who would graduate first in his class from Yale Law School. After being turned down by the 30-odd white-shoe firms he applied to—the explanation is anti-Semitism—he eventually scored a clerkship with Supreme Court Justice Arthur Goldberg, and from there, a professorship at Harvard Law School.

Dershowitz came of age in an era of liberal ascendancy. “Jews have always been caught between the black and the red—between the extremes of communism and fascism,” he says. The stated purpose of his latest book, Electile Dysfunction, which Dershowitz has brought along with him today in his coat pocket, is to explain the 2016 presidential election through the lens of populist extremism, with the white nationalism of today’s alt-right and the identity politics of today’s far left standing in for the black and the red of earlier eras. Filled with digressions about pet topics, it’s not the best book Dershowitz has written. It’s also not, at its heart, about the election that just concluded, but about Dershowitz’s own sense of political alienation. “I do feel very much out of the mainstream on university campuses,” he says of the arena he left just three years ago. Lately, Newsmax and, if he’s lucky, Megyn Kelly are more interested in his work than Charlie Rose or Rachel Maddow. It’s not for nothing that he’s calling his next book Why I Left the Left but Couldn’t Join the Right.

Many never considered him a man of the left to begin with. His interventionist foreign policy views and fervent Zionism have long repulsed critics like MIT’s Noam Chomsky, who told me over email that he finds Dershowitz’s “polemical work utterly appalling.” Dershowitz’s newest beef, though, isn’t with Chomsky or his fellow travelers, but with a new generation of progressives who, broadly, aim to prevent privileged groups from doing harm to less privileged groups. Dershowitz has no issue when that means stopping unwarranted police violence against young black men, or unwanted sexual advances from toadish cable-news overlords. But when it comes to the subtler manifestations of harm prevention, his hackles are raised. “Safe space” and “trigger warning” and “microaggression” have become familiar terms. In the Deep Throat era, Harvard students tended to fight against the censors. Now, many of them have joined their ranks. Naturally, all of this spooks the free-speech absolutist. “We often forget that the benign-sounding term ‘political correctness’ originated under Stalin,” Dershowitz writes in Electile Dysfunction. “Extremists begin by banning and burning books, and they end by banning and burning people.” (The book is not as lighthearted as its title would suggest.)

Campus political correctness isn’t new for Dershowitz. He was yelling about it in the 1980s and 1990s. To Dershowitz, though, it isn’t just certain words that are getting thumbs-upped and thumbs-downed. It’s groups of people: “Christians on campus are not oppressed, conservatives on campus are not oppressed, Jews on campus are not oppressed. Only Palestinians and gays and transsexuals are oppressed.” The coddling such groups receive, he argues, obviates their claims to victimhood. “There is no ‘white privilege’ on college campuses. There is privilege for people who claim the mantle of oppression.”

The off-campus manifestations of the movement unsettle him, too. “People who now call themselves progressives—say, Black Lives Matter—are not progressives,” Dershowitz says. “They’re identity politics [people]. Only black lives matter. And only black lives matter when white policemen, or other policemen, kill them.” There’s irony here. In the 1990s, Dershowitz popularized the term “testilying” to describe the routine perjury committed by police officers questioned in court. At the time, he was a vocal and prescient skeptic of the American criminal justice system. (Famously, the O.J. Simpson defense team capitalized on African-American mistrust of the L.A. Police Department.) But now that the issue has entered the mainstream, he seems to have lost interest. Instead, he chides tenured professors for capitulating to PC culture and gives free legal advice to college men who say they’ve been falsely accused of sexual assault. The progressive pendulum, he believes, has swung too far, at the expense of free speech and due process: “It’s difficult to fight back. If you do you’re called a racist or a sexist or a homophobe.”

After a 10-minute Newsmax hit and a cup of to-go soup for lunch, Dershowitz and I walk to his next appointment, at Reuters in Times Square. The occasion is a broadcast interview—topic: Electile Dysfunction—with Sir Harry Evans, the storied, semiretired British journalist who keeps referring to the book as Erectile Dysfunction. The interview is meant to air live on the publication’s Facebook page; we sit in a makeshift green room and wait to be summoned.

A sprightly young Reuters employee named Yahaira brings us two bottles of water.

“What a beautiful name: Yahaira,” Dershowitz says genially. “Where does it come from?”

“I’m Mexican. My parents are Mexican,” Yahaira says.

“Are you a rapist?” Dershowitz asks, an incongruously pleasant smile still plastered on his face.

Errrr. Yahaira manages an approximation of a laugh. “Not at all.”

Dersh doubles down. “You’re not a rapist and you’re from Mexico?!” he asks in a mock-incredulous tone. There is panic in her eyes now. Dershowitz, still grinning, shakes his head and asks aloud, “What do you think of that guy?” It turns out he has been attempting to satirize Donald Trump. Slowly, shoulders untense and business resumes more or less as usual.

Depending on your point of view, this was either a harmless attempt at humor or, you know, a racially obtuse microaggression that only an old white guy would find funny.


Dershowitz, despite the megawatt career, has never been a glamorous figure. At the height of his fame, he looked most comfortable not at the side of his celebrity clients but in his cramped Harvard office, wearing oversize aviator eyeglasses and itchy-looking sweaters. His social profile began to improve in 1996 upon meeting the financier Jeffrey Epstein through Lynn Forester de Rothschild, a Martha’s Vineyard friend. She told him Epstein was a brilliant autodidact who loved meeting interesting people. Epstein visited Dershowitz in Cambridge, sent him a thank-you bottle of wine, and a week later called to invite him to the 59th birthday party of Victoria’s Secret founder Leslie Wexner. “I said, ‘Who’s going to be there?’” Dershowitz tells me. “[He said], ‘Shimon Peres is going to be there. Senator [John] Glenn, the astronaut. Alfred Taubman, the head of Sothebys.’” Dershowitz was in.

Dershowitz had represented the fabulously wealthy before, but had never been friends with anyone on Epstein’s level. There was a ranch in New Mexico, a mansion in Palm Beach, a private island in the Caribbean—plus Epstein’s primary residence, a 50,000-square-foot townhouse said to be the largest in Manhattan. Dershowitz was bowled over. “I met Prince Andrew through him. I mean, I’m a kid from Borough Park, an Orthodox, poor community, hanging around with a prince, and [scientists] who were going to win the Nobel Prize. That’s pretty thrilling.”

Epstein, who also became close with Harvard grandees such as Larry Summers, made a $30 million donation to the university. Dershowitz, in turn, began flying on Epstein’s jet and hanging out in Palm Beach. Dersh, like everyone else, didn’t necessarily understand how Epstein had become a billionaire. J. Epstein & Co. had only one known client: Wexner. But Epstein’s intellect was obvious, and he had a knack for gaining the trust of the cognoscenti. “I’m on my 20th book,” Dershowitz told Vanity Fair in 2003. “The only person outside my immediate family that I send drafts to is Jeffrey.”

Then, two years later, the Epstein fairy tale ended abruptly. In 2005, Palm Beach police interviewed a 14-year-old girl living at a juvenile facility who said she had been paid to remove her clothes and massage Epstein while he masturbated and touched her with a vibrator. All told, police identified close to three dozen girls and women who were alleged to have worked for Epstein in a similar capacity, operating on a referral system. Some showed up at Epstein’s mansion just once; others told investigators they’d gone more than 100 times. After they had finished their sessions with Epstein, they said, they were sent packing with approximately $200 in cash, depending on how sexual the “massages” were. Epstein’s lawyers said he never knew the young women were underage.

When Palm Beach police began rifling through the sex toys and photographs of nude females scattered around his home, Epstein lawyered up. Dershowitz says he resisted Epstein’s request for representation—he was his friend, not his lawyer—but eventually gave in. Epstein hired investigators to trawl his accusers’ MySpace pages for mentions of drug use, alcohol abuse, and sexual references. Dershowitz took the materials to state prosecutors, who began to worry about the credibility of potential witnesses, and charged Epstein with just one count of solicitation of a minor for prostitution. Dershowitz was also instrumental in striking a deal with the U.S. Attorney’s Office that guaranteed federal charges wouldn’t be brought against Epstein. In 2009, after spending 13 months in a county jail and registering as a sex offender, Epstein was out, and soon paparazzi were photographing beautiful women leaving his mansion.