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The Judge Didn't Seem Impressed by Dershowitz's Arguments

Vivia Chen

September 26, 2019

Loretta_A._PreskaNews alert! Alan Dershowitz and Boies Schiller Flexner are in agreement on a vital issue: They both think U.S. District Judge Loretta Preska of the Southern District of New York is awesome!

“She was extraordinarily well-prepared and asked the right questions,” praised Dershowitz when I asked him about his hearing before Preska on Tuesday, where his lawyers argued that Boies Schiller be disqualified from representing Virginia Roberts Giuffre, one of Jeffrey Epstein’s alleged victims, in her defamation case against him.

“She’s intelligent, well-prepared and paid careful attention,” lauded Sigrid McCawley, the Boies Schiller partner who’s representing at least six of Epstein’s alleged victims, when I met with her after the hearing.

Are both sides saying such nice things about the judge because they want to be in her good graces? Undoubtedly.

Speaking as an observer, I have to tell you I was also quite taken by Preska. She’s sassy, sharp and funny. In short, she’s got that don’t-waste-my-time New York style that all judges should have.

But enough about my latest girl-crush. Here’s what you really want to know: Who scored points at the hearing?

If Preska’s deployment of sarcasm is any indication, I’d say that the Dershowitz team should be sweating. The judge asked pointed questions to both sides but I thought she was a lot more skeptical of the arguments that Dershowitz’s legal team was putting forward.

A number of times, Preska said to Dershowitz’s lawyers, Howard Cooper and Imran Ansari, about their arguments, “I don’t get it.” For instance, Preska asked why Dershowitz failed to raise the conflict issue about Boies Schiller’s representation of Giuffre in previous litigations related to the Epstein matter, though the professor made noises about doing so. (Dershowitz claims that Boies Schiller has a conflict because its partner Carlos Sires had offered to represent him after Giuffre accused the professor of sexual abuse, and that he had sent the firm confidential information as a result.)

When Dershowitz’s lawyer Ansari argued that he’s now raising the conflict issue because he’s being directly sued for defamation, Preska was unimpressed and shot back, “What difference should that make?”

Nor was she impressed by Ansari’s suggestion that Boies Schiller used dirty tactics. “Why are you telling me this?” Preska asked. “I don’t care.”

And she seemed even more unconvinced that Dershowitz had established a client/lawyer relationship with Boies Schiller that would merit the firm’s disqualification. She noted that when told by Sires that the firm could not represent him, Dershowitz replied in an email: “Darn. I was really hoping that you could come on board.”

Preska hammered away at that response.

“It’s the subjunctive,” she said. “He’s not writing back and saying, ‘Holy Moly, you said you’d represent me.’ He’s saying, ‘I was hoping you could do it.’”

At that point, Ansari looked stumped. He reminded me of myself as a law student during moot court. Scared. There are lots of other moments when Preska seemed to diss Dershowitz’s lawyers’ arguments, but why dwell on them? (His other lawyer Cooper didn’t seem to get clobbered as badly as Ansari.)

Which brings up some other curious scenes during the proceedings: The multiple times that Dershowitz impatiently nudged his lawyers with notes and comments while they were speaking to the court, as if he wanted to jump up and take over his own defense. Could it be that he was angry with his lawyers and thought he could do a better job?

Not at all, Dershowitz told me.

“I love it when clients are interested and pass notes to me during trial,” he said. “I’m not second-guessing [my lawyers]. I happen to know the case better than anyone else.”

So did he think that the judge was a lot tougher on his team and that her ruling could go against him? Nope. “I learned a long time ago not to speculate.”

Coming from one of the lawyers on the O.J. Simpson defense team, the professor has a point.


Twitter: @lawcareerist


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The Careerist takes an inside look at how lawyers shape their careers and manage their lives. The blog aims to dissect developments in the profession, provide useful information and advice, and give lawyers a platform to voice their views. The goal is to provide a fresh, provocative take on the state of lawyering.

About Vivia Chen

Vivia Chen

Vivia Chen, The Careerist's chief blogger, has been covering the business and culture of law firms for a decade. A former corporate lawyer, Chen is fascinated by those who thrive (as well as those who don't) in the legal profession. Her take: Success in the law (and life) doesn't always travel a linear path. If you have topics you'd like to discuss or information to share, contact her: VChen@alm.com

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