Ten years after O.J. Simpson was acquitted of murder, one of his lawyers, Alan Dershowitz, admitted that “sometimes you lose sleep at night” while working as a defense attorney.

“Every lawyer who’s also a good person has these ambivalences,” he told PBS in 2005.

It might seem unlikely introspection for an outspoken lawyer whose high-profile career has been marred by his association with a now-dead pedophile, Jeffrey Epstein, and who has now become a member of President Trump’s impeachment legal defense team.

After months of fiercely defending the president on Fox News, Dershowitz said he will argue constitutional issues on the Senate floor.


Dershowitz said his goal is to “defend the integrity of the Constitution and to prevent the creation of a dangerous constitutional precedent” by removing the president from office.

Laurence Tribe, a Harvard law professor who supports Trump’s impeachment, said Dershowitz is an “aggressive, persistent, fairly knowledgeable, quite imaginative and generally creative” lawyer who will bring “an unrealistic and unwarranted degree of self-certitude” to the trial.

“He tends to be self-righteous in a way that convinces him, but not those whom he needs to persuade, that everyone but him is a hypocrite,” Tribe said.

Dershowitz will hold a unique place in the constellation of Trump’s lawyers, past and present. Most have acted, at least in part, as fixers and hatchet men, like Roy Cohn, Michael Cohen or even Rudolph W. Giuliani, whose attempts to dig up dirt on the president’s political enemies in Ukraine has led to the current impeachment proceedings.


But Dershowitz — constitutional law scholar, former Harvard Law School professor, brand-name legal commentator — is an emissary from a more rarefied world that Trump has always found alluring.

The president loves quoting Dershowitz’s cable news appearances on Twitter, and he’s sought out Dershowitz, an ardent supporter of Israel, for advice on Middle East politics.

President Trump speaks to Alan Dershowitz, right, at Christmas Eve dinner at Mar-a-Lago in Palm Beach, Fla. (Andrew Harnik / Associated Press)

Long before Trump, Dershowitz reveled in taking on controversial clients.


In 1982, he represented socialite and financier Claus von Bulow, who had been convicted of trying to murder his wife in a case that involved adultery, enormous wealth and intense media interest.

Dershowitz successfully appealed the conviction and then won an acquittal in a second trial. His book about the case was turned into a 1990 movie of the same name, “Reversal of Fortune.” It won an Academy Award for Jeremy Irons, who played von Bulow. Dershowitz was played by Ron Silver.

Although he says he voted for Hillary Clinton and opposes some of Trump’s policies, last year Dershowitz wrote “The Case Against Impeaching Trump.” The president issued an endorsement, calling it “a new and very important book.”

Dershowitz wrote the book before the Ukraine scandal erupted in September, but Dershowitz says he is unimpressed with the case that House Democrats sent to the Senate this week for trial.


“The articles of impeachment simply do not charge constitutionally impeachable offenses,” he said in an interview.

Trump is accused of abusing his power by asking Ukraine to launch investigations that would benefit him politically and then obstructing Congress by directing administration officials to ignore subpoenas for documents and testimony.

Abuse of power is not a “high crime or misdemeanor,” Dershowitz argued, because it’s too vague and the framers of the Constitution “didn’t want open-ended criteria that could be weaponized” for impeachment.

Dershowitz also said it’s dangerous to impeach the president for obstruction of Congress because the executive branch often pushes back against legislative requests, and it’s not improper for Trump to want the issue to be litigated in court rather than immediately complying.


“The president was simply invoking his right to check and balance the legislature through the courts,” he said.

Dershowitz claims his principled defense of Trump has caused his liberal friends to shun him, a sign of what he describes as militant partisanship that’s dividing the country.

He’s no longer welcome at some dinner parties on Martha’s Vineyard, the heavily Democratic Massachusetts island that has been an elite retreat for the cultured and powerful, Dershowitz wrote in a much-mocked column for The Hill.

Critics accused Dershowitz, who continued to visit the island, of simply trying to stir up book sales.


Dershowitz’s defense of Trump isn’t the only thing that has generated concern. There’s also his association with Epstein, a convicted sex offender.

In 2008, Dershowitz helped the wealthy financier secure a cushy plea deal with federal prosecutors in Florida while Epstein was under investigation on suspicion of sexually abusing underage girls.

A decade later, a Miami Herald investigation disclosed details of the deal for the first time, spurring outrage among Epstein’s victims.

Federal prosecutors in New York opened their own investigation, leading to Epstein’s arrest last July on charges of sex trafficking of minors and conspiring to commit sex trafficking of minors.


Epstein died by suicide the following month while awaiting trial in a Manhattan jail, but the investigation continues to reverberate through the court system.

One of Epstein’s victims, Virginia Roberts Giuffre, has accused Dershowitz of abusing her. He’s denied the allegations and filed a lawsuit against her for defamation.

Dershowitz’s most recent tweets urged his critics to pick up his book where he lays out his defense.

“To all my Twitter detractors who presume, despite the overwhelming evidence to the contrary, that I engaged in sexual misconduct, I’ve made my new book — Guilt by Accusation — available on kindle for $1.98 (no royalties for me). I challenge you to read it then Tweet,” he wrote.