Jerold Oshinsky – Chambers USA 'Lifetime Achievement Award' winner

5 minutes with... Jerold Oshinsky

When did you decide to become a lawyer? Why? 

I read Clarence Darrow’s autobiography when I was 12 and decided that I wanted to be a lawyer. Coming from a lower middle class family, announcing that I wanted to be a “lawyer” gave me prestige in my own 12-year-old mind. I was the first in my extended family of dozens of aunts, uncles and cousins to attend college and become a professional.

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

I began at a “Wall Street” firm, expecting that I would work hard and long and someday become a partner trying securities and antitrust cases in New York.

Has it lived up to your expectations? 

It definitely has lived up to my expectations but in ways I could not have foreseen. I “worked hard,” “became a litigator” and “became a partner.” The scope of my work was varied and much different than what I had expected in terms of subject matter.

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

I got into Insurance Coverage Litigation by chance. A client had an asbestos insurance problem and the result in that case became the most famous decision in the field. That led to many other clients asking me to represent them on insurance issues, and they still do. 

What do you consider to have been your big break? 

The decision in the asbestos case altered my career path. It also changed where I practiced. The litigation was in DC, and for that reason, and others, we moved from New York to the Washington, DC area.  

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

The market is much more competitive today. There used to be a few firms that handled Insurance Coverage for policyholders; now many more seek to compete despite the fact that many of those firms represent insurers and at the same time seek to also represent policyholders, or think they can.

What achievement are you most proud of? 

My five grandsons are my greatest legacy, along with my wife and I celebrating almost 50 years together.

"Either you realize that the law is a 24/7 occupation in order to succeed, or you should do something else." 

What do you consider your greatest failure or regret? 

I regret not being 6’6” and playing professional basketball. I also regret not accepting a clerkship or justice department position as a young lawyer when they were offered to me. I went instead to “Wall Street.” 

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

While having a landmark decision was very satisfying, I have most enjoyed the friendships and contacts I have made with colleagues, clients and adversaries. Some of my best cases have come from referrals from my adversaries.  

And enjoyed least? 

I have least enjoyed being on the road and away from my family. I also do not enjoy the time I need to spend on billing, and the concept of the hourly rate.

What law would you change, abolish or create? 

I would get the government totally out of addressing private social and relationship issues.

Who is your legal hero? 

Charlie Pickett was a partner at Chadbourne, my first law firm. He was brilliant and was my mentor. He taught me all the basics I use today and try to pass on to young lawyers, but, in my mind, never quite to his level of expertise and brilliance. Gene Anderson is a close second.  

What career would you have in your second life? 

Commissioner of Basketball. When time allows now, I act, direct and produce plays, usually with historical themes.  

What slogan would you like to be remembered by? 

“Just ask Jerry. He remembers everything!”  

What advice would you give to students trying to enter the legal profession today?

Study art history and theater. There is no way to prepare in advance to practice law. Either you realize that the law is a 24/7 occupation in order to succeed, or you should do something else.  

And secondly, to those who hope to ultimately get into the areas of law in which you are expert?

The law today is changing with every new decision. There are exciting new issues evolving in my area – data and privacy issues being most noteworthy. Prepare yourself with a diverse liberal arts background that has nothing to do with the “law”. You will learn the “law” when you are a practicing lawyer.