Gerald Shargel – mafia lawyer

When did you decide to become a lawyer? Why? 

Back in college I was a bartender. Well I wasn’t going to do that all my life, so I next thought of being a trial lawyer. There’s a profound similarity between bartending and trial work – in both professions you need to be able to tell a good story.

Starting out, what did you expect from a career in the law?

I had no expectations. I didn’t plan or plot my career. With me it was "this happened, then that happened" and so on, right down the line. One high-profile case followed another and then another.

Has it lived up to your expectations?  

I guess I surpassed my expectations because I really wasn’t expecting anything. That’s not to say that I didn’t have confidence in myself; I was a friendly outgoing person and thought that I would succeed by the sheer force of personality.

How did you get into the areas of law you are known for today? By design? Chance? Both?

I’ll call it luck. When I came to New York to go to law school I didn’t know a lawyer. It turns out that my wife’s uncle, the proprietor of a dry cleaning store, had a well-known judge as a regular customer. Her uncle introduced me to the judge who took a liking to me and "boom", my career was jump-started. Lots of funny details along the way, but rest assured, a mentor is a good thing to have.

What do you consider to have been your big break?

See above. Find mentor.

What differences do you see in today's legal market compared to when you started?

Two differences immediately come to mind. First, when I graduated from Brooklyn Law School, a law-related job was available to anyone who wanted it. Career opportunities were abundant. As everyone knows, "today’s legal market" is 180 degrees different; today frustration and disappointment abound in what continues to be a sluggish market. The second difference is that it’s hard, if not impossible, to gain the trial experience that could be had during my era. I have had some 125 jury trials. Today, 96% of all federal criminal cases are resolved by guilty plea. It’s almost impossible to get my trial experience with all of those guilty pleas.

What achievement are you most proud of?  

In 2003 I became the practitioner-in-residence at Brooklyn Law School, teaching Evidence as well as a variety of Criminal Law subjects. Over the last 11 years I have had literally hundreds of students in my classes, many of whom now have successful legal careers. I love reading about and hearing about former students and my pride is palpable when a former student comes up to me and tells me how much she or he enjoyed my classes. I guess that the ones who didn’t enjoy my classes don’t come up to me.

What do you consider your greatest failure or regret?

Honestly, I have no regrets. I’ve had a great career, practicing as a criminal defense lawyer for 44 years and still going strong. Over these many years I’ve met a lot of interesting people, litigated a lot of interesting issues and have been involved in a lot of high-profile cases. I write, I teach and I litigate. What could be better than that?

What have you enjoyed most during your career in the legal profession?

The challenge of having someone’s liberty or even life in your hands. In my entire career I have tried only one death penalty case. It was not something I 'enjoyed' but it obviously was my biggest challenge. When the jury rejected the death penalty my emotions got away from me.

Why did you choose to swap private practice for BigLaw at this stage in your career?

BigLaw, as you put it, has given me the opportunity to broaden my horizons. As long as I practice, I will be first and foremost a criminal defense lawyer. But I would like to try different kinds of cases as well. Each case brings with it the opportunity to learn something new, to try something different.

Are the skills you developed as a highly successful criminal defense litigator useful in your new role at a big corporate law firm? If so, which and how?

Of course that’s true. The skill set of a criminal lawyer easily translates for a civil case and, I believe, vice versa. While there may be different substantive and procedural rules, an opening is an opening, cross-examination is cross-examination, whatever the nature of the case.

I know it has only been a short while, but how does your new role compare to life as a sole practitioner?

When I joined the firm I brought my three associates with me. They are three wonderful lawyers. But the support that I’ve been given at Winston & Strawn is something that was beyond my imagination.

What law would you change, abolish or create? 

I would abolish criminal sanctions for the sale, use or possession of marijuana. We now live in a country where people face draconian prison sentences for marijuana offenses while other sovereigns within our borders allow sale and recreational use of the drug. Marijuana should be legalized and heavily taxed.

Who is your legal hero?  

Easy one. Judge Henry Friendly who sat on the 2nd Circuit Court of Appeals for more than 25 years. He was often described as the greatest judge of his era.

What career would you have in your second life?

Screenwriter.

What slogan would you like to be remembered by? 

As it was once said of New York Yankee catcher Thurman Munson: “He came to play and played to win.”

What advice would you give to students trying to enter the legal profession today? And secondly, to those who hope to ultimately get into the areas of law in which you are expert?

I would first say, be true to yourself. Would you really enjoy and comfortably be able to withstand the pressure of performing as a trial lawyer