I was very excited when Alan Dershowitz agreed to let me interview him for Coverage Opinions. After all, his schedule is frenetic, I’m not exactly Larry King and insurance is no doubt low on the list of legal topics on his mind. While he just published a book, it is his 31st and six of them were national bestsellers, including Chutzpah, which went to #1 on The New York Times bestseller list. So I am certain that he was not looking at my little insurance newsletter as some sort of promotional bonanza for his latest book. It is clear that Dershowitz was simply doing a nice thing when he sent me a couple of e-mails on a Saturday essentially saying – Here’s my number. Call me Monday at 11. And he could not have been more gracious on the phone. It was really a thrill to speak with one of the most preeminent lawyers of our time. My parents told everyone they know.

Dershowitz’s many books cover such topics as civil liberties, specific cases, various aspects of the legal system, Israel and the Middle East and even fiction. But his latest is different. While all of those topics are discussed, Taking the Stand – My Life in the Law is also very personal.

Alan Dershowitz’s story is well-known. He is the youngest ever professor at Harvard Law School (just retiring after 50 years there) and has been a part of or led the defense team for many famous, or infamous, clients, such as Bill Clinton, Julian Assange, O.J. Simpson, Claus von Bulow, Mia Farrow, Jeffrey MacDonald, Patty Hearst, Mike Tyson, porn star Harry Reems (of Deep Throat fame) and the list goes on. His representation of von Bulow was the subject of a book and movie – Reversal of Fortune. [Jeremy Irons played von Bulow and won the Academy Award for Best Actor.] Dershowitz has also advised many in legal, political and other matters, such as President Obama, Benjamin Netanyahu, Ted Kennedy, Brando, Sinatra, Michael Jackson, Elie Wiesel and countless other celebrities and high ranking public officials.

Something I’d always wondered about Dershowitz was answered head-on in his book. Despite his incredibly impressive client list, yes, there is a downside to hiring him as your lawyer. Some people hate him and his involvement may raise the profile of your case in the media. This is all explained to prospective clients in “the warning” as he calls it. Another risk he cautions about is that “[p]rosecutors sometimes work harder when I am their opponent, because they think that beating me in court will be a kind of trophy.”

I asked Dershowitz if his celebrity causes judges to give him a more difficult time during oral argument. For the most part – no. He feels that most judges enjoy having him before them because he comes prepared, with a carefully worked out argument, and that’s what they want – and it’s something that they don’t always get from lawyers. But he also told me that there are some judges, who perhaps lack self-confidence, and are worried that people will think that they are not up to job, that can be tough on him.

Besides his well-known cases, Dershowitz has also served, pro bono, as appellate counsel to numerous convicted individuals in their attempts to win post-trial exoneration or some other type of relief. Of course, for this work he has made his share of enemies. While the right to counsel is a bedrock principle of our legal system, some people just don’t get that and simply see him as a gun hired to free the guilty. This generates hate mail, some really visceral, that Dershowitz hangs on his office door to show students what to expect if they become public figures.

Not surprising, Dershowitz’s pro bono efforts do not get the same attention as his work for celebrity clients. Indeed, he knows that his eventual obituary will emphasize his cases representing the famous. This is very troublesome to Dershowitz. Since he has had a life-long practice of setting the record straight with regard to things written about him, he has penned a letter to the editor to be sent after his death. Among other things, his posthumous response to his obituary states: “Your understandable emphasis on my high-profile cases distorts my record by downplaying the numerous pro bono cases I handled on behalf of obscure and indigent clients. I made it a policy throughout my life to devote at least half of my professional time to nonpaying cases and causes.”

Dershowitz’s work on behalf of obscure and indigent clients results in requests for his services from individuals who believe that they have been wrongly convicted and are looking for justice from the appellate courts. I am sure that many of these requests sound sympathetic and describe grave injustices that the writers believe have befallen them. I asked Dershowitz how he chooses which pro bono appellate cases to take.

While he explained that it is a combination of factors, and hard to quantify, there is one mandated requirement: “I have to get pissed off.” He told me that he has to get angry – the trial court acted unfairly toward the defendant, the jury was prejudiced or the prosecution overreached. Taking an appeal, he explained to me, is a huge time commitment. “So to take on that kind of commitment I really have to be motivated and the motivation comes from a sense of outrage. So it’s as much emotional as it is intellectual.” And still there are other factors that militate in favor of his selection of a case. He explained to me that he prefers very hard and challenging cases, ones that everyone says you can’t win and he prefers less popular defendants to popular ones. He told me that, given the vast amount of time involved to do everything needed to handle an appeal (and to do so his no stone unturned way), he is only able to take on about a half dozen of these cases per year.

As I said, Taking the Stand is very personal. Dershowitz describes his upbringing in Brooklyn’s Boro Park, a Modern Orthodox community of second generation Jews. His family was not able to afford luxuries and it provided little in the way of books, music, art or secular culture. He attended a yeshiva high school and was a terrible student. He hated his teachers and the feeling was mutual. His love for conflict, doubt and debate was simply not appreciated by the teachers.

But everything changed when he got to Brooklyn College and Yale Law School, where he excelled. At Yale he was first in his class and elected editor in chief of the Yale Law Journal. From Yale Dershowitz served as a law clerk for Judge David Bazelon of the D.C. Circuit Court of Appeals and then Justice Arthur Goldberg of the United States Supreme Court. An important aspect of his time with Justice Goldberg was the planting of seeds to abolish capital punishment. The efforts ultimately succeeded, even if it was short-lived.

Autobiographers usually feel the need to begin their effort with a description of their formative years. After all, is there a more logical place to begin an autobiography? This sometimes makes for reading that is deadly dull and adds little to the story. But Dershowitz’s pages on his formative years are nothing of the sort. They are as interesting as everything else in Taking the Stand. As you progress through the book it becomes clear that Dershowitz’s formative years played a large part in shaping his long career that was to come.

What makes Taking the Stand such a compelling and enjoyable read is that it is several books in one. Of course it is Dershowitz’s autobiography. But he recounts his life in the law through his personal involvement with others. So in that sense it is also biographical of the people that he discusses – some clients and some not. And since these discussions generally center around legal issues, Taking the Stand is itself also a law book – but one that is infinitely more enjoyable than any case book I’ve ever read.

For example, there is no shortage of books and other writings on the subject of rape prosecutions. But to learn about it from Mike Tyson’s appellate lawyer, and hear the conversation that Dershowitz and Tyson had, in Tyson’s hotel room the night before his sentencing, is not the ordinary backdrop for such discussion.

These days murder investigations are as much about science as the work of gum shoes. Dershowitz touches on the scientific aspects in the context of his representations of Claus von Bulow and O.J. Simpson. This is far more interesting than a discussion of the subject without such context. Not to mention that Dershowitz reveals that, just as Johnnie Cochran was about to deliver his closing argument, Marcia Clark whispered to him: “When you’re up there, I want you [to] think of only one thing: I’m not wearing any underwear.”

Taking the Stand is a collection of dozens of stories of Dershowitz’s involvement in interesting cases (celebrities and otherwise) over a long career. These include cases (and causes) involving capital punishment, false confessions, obscenity, disclosure of government secrets, media and the law, terrorism, church and state, the Holocaust, defamation and privacy, Israel and so many more. Dershowitz never stays too long on any one topic, so there is never a chance for the discussion to get bogged down in tedium. To me, that’s what makes or breaks a non-fiction book.

The book also includes numerous short vignettes that generally describe Dershowitz’s experiences (jury duty, walking out on Warren Burger) or encounters with famous people – including some that he calls out for unacceptable behavior that such people probably thought they’d never see in writing (such as Leona Helmsey and Bobby Fisher). Much more positive experiences are described in vignettes about Gorbachev, Mitterrand and Justice Brennan.

It becomes clear throughout Taking the Stand that humor, especially Jewish humor, has played an important part of Dershowitz’s life. He says that he uses humor in the courtroom, classroom and every other aspect of his life. He describes joke telling as a youth as a “competitive sport” among friends. Perhaps there was something in the air as he grew up two houses down from Jackie Mason, Elliott Gould lived around the corner, Buddy Hackett was a few blocks away in his uncle’s building and Woody Allen, Mel Brooks and Larry David were in nearby neighborhoods. Dershowitz’s first job was as a deli guy in a kosher delicatessen on New York’s Lower East Side. A good Jewish deli is really just a comedy club where the comics wear white aprons. Dershowitz credits his work as a busboy in the Catskill Mountains, over the Jewish holidays, as a source of many of the jokes he knows.

Of course, being a stand-up comic myself, I had to ask Dershowitz about his love of Jewish humor and I even suggested that he give stand-up comedy a try. He told me that he thinks he knows every Jewish joke every invented by anyone. He says proudly that he has held his own with many of the best, including Larry David. Of course, Dershowitz notes, the pros write their own material and he admits to just telling other people’s jokes.

As for trying his hand at stand-up, his response was overwhelmingly enthusiastic: “Get me a gig! Get me a gig!” He told me that he almost tried stand-up comedy. A few years ago a fund raiser called Stand-up for Harvard was planned where various professors were to do stand-up routines. Dershowitz signed on but it never came to fruition. “I think they couldn’t find enough funny Harvard professors,” he suspects.

Obviously I had to find an insurance coverage angle for the discussion. Although as soon as I mentioned insurance Dershowitz was quick to tell me that he had something to say on the subject. He believes that insurance companies have far too much say whether criminal cases for fraud are brought. He feels that prosecutors defer to the expertise of the insurance company who they believe have handed them a case on a silver platter. By doing so the prosecutors do not do the hard work necessary to investigate the case themselves. This results is some weak cases being brought.

Insurance fraud is one thing, but there is no way that I was getting off the phone without some mention of insurance coverage. In Taking the Stand, Dershowitz is highly critical of those who use the well-known first amendment exception -- freedom of speech does not protect someone who falsely shouts fire in a theater -- as an analogy to support censorship in various contexts. He provides examples of how the analogy is not only inapt but even insulting.

Shouting fire in a theater may be, according to Dershowitz, the only jurisprudential argument to have achieved the status of a folk argument. The saying is attributed to Oliver Wendell Holmes. Although Dershowitz calls out Holmes for having borrowed the phrase, without attribution, from an obscure prosecutor.

Given that Dershowitz has been a long-time student and teacher of this famous phrase, I asked him if it is constitutionally protected free speech to stand in a movie theater, with a claim file, and shout: “Is this fire claim covered?” He laughed. And being a good sport he set out to answer. The question must be examined in context, he explained. It is constitutionally protected free speech as long as you don’t use fire as the central word and whisper all of the others.