Lawyer Limelight: Sean O'Shea

Photo by Greg Endries.

Sean O'Shea's father thought he was "crazy" to leave a prominent law firm like Latham & Watkins to take a job as a federal prosecutor in New York, but the move paid dividends for the young litigator in the form of invaluable trial experience. Over a 10-year stint, O'Shea tried more than 35 federal trials and ended up heading the Business and Securities Fraud Unit of the U.S. Attorney's Office for the Eastern Distrcit of New York.

O'Shea confounded his father again by then starting his own practice instead of returning to law firm life. The benefit of this more difficult path is that New York-based O'Shea Partners, founded in 1996, has allowed him to take a wide range of civil and criminal litigation for individuals and businesses without fear of conflict, including on the plaintiffs' side.

O'Shea did his undergrad work at the University of Illinois and received his J.D. from Northwestern University School of Law. He began his career in Chicago before leaving for the U.S. attorney's office in New York.

Lawdragon: With your B.A. received in ’78, and your J.D. in ’81, it seems that you went pretty much straight to law school after college. When did you know you wanted to become a lawyer? What led to your developing an interest in the law?

Sean O’Shea: I wanted to be a lawyer from a young age. I do recall teachers mentioning to me that I should be a lawyer because I was somewhat argumentative and would often present alternative ways to look at issues.

LD: How about your decision to become a trial lawyer? Was there a course or professor at Northwestern, or an experience early on as a practicing lawyer, that convinced you that being a litigator who tried cases was right for you?

SO: I wanted to be a trial lawyer because the idea that I had of a lawyer was of an advocate fighting in court. I was inspired by legendary criminal trial lawyers in Chicago, such as Pat Tuite and John Powers Crowley, where I began my practice of law after law school. They encouraged me to seek a position as an Assistant U.S. Attorney.

LD: Many lawyers who arrive at large firms stay there, or at least hope to. What was your motivation for leaving private practice to begin a stint at the U.S. attorney’s office in New York?

SO: I left a great law-firm environment at Latham & Watkins, working with inspiring lawyers to pursue a job at the U.S.  Attorney’s Office because it is a recognized way to learn the craft of trying cases in federal court. I was able to immediately assume a leading trial role in jury trials that continued for 10 years.

LD: You eventually assumed a leadership position there and worked on many high-profile cases. Nevertheless, is there a case or experience that stands out to you as particularly memorable, or one you find yourself reminiscing about more than others?

SO: My practice at the U.S. Attorney’s Office eventually resulted in specialization in corporate and white-collar crime, and I had the irreplaceable experience of facing off against the best of the white-collar bar in New York and Washington, D.C. Perhaps my most memorable case was one not in my area of specialization. I was asked to take over a case that was in disarray right before trial. It involved an arson and fraud in which a heroic firefighter had died trying to save trapped upper-floor occupants of a commercial building. It involved able and well-funded defense counsel, sophisticated forensic proof, a legendary trial judge with the Honorable Jack B. Weinstein, difficult evidentiary issues and several difficult cross-examinations of expert witnesses.

It held all the drama that you could seek in a jury trial and resulted in a hard fought victory. Ultimately, a book was written about it. And to make it really memorable my first child was born the day after the jury returned its verdict.

LD: Once returning to private practice, why did you decide to start your own firm, as opposed to practicing at an existing partnership?

SO: When I left Latham for the U.S. Attorney’s Office, my father said I was crazy to leave that renowned firm for a government job. He thought I had really lost it years later when I left the U.S. Attorney’s office and I told him I was not planning to take any of the offers of partnership at a large firm and instead start my own firm. I knew that it would be harder at first to do it this way, but I wanted to practice conflict free and take any case I wanted. And it has worked out that way.

I have been able to represent individuals as well as corporations and investment funds on the plaintiff side unimpeded by formal and informal conflicts. I have also been able to do very interesting financial contingency cases that have added a dimension to my practice that would not have existed if I had returned to big-firm practice. That has led overall to a much more exciting practice.

LD: Many law students aspire to have a successful litigation practice like yours, where they actually get to try high-stakes cases. What advice would you give them?

SO: I would advise young lawyers that sometimes the path is not necessarily a straight one. I am a believer in the merits of big-firm experience because it teaches thoroughness and how to produce first-rate work product through the expenditure of great effort. One must recognize, however, that success there may not be an end in itself. You need to be ready to leave your comfort zone and try other things to attain real career satisfaction.

LD: You’ve been noted as an expert in cross-examination. Is that your favorite part of trying cases, or is there another favorite aspect of trial work, and why?

SO: Cross examination is the hardest thing trial lawyers do. It is my favorite part of trial because it is the most difficult and can lead to unexpected disclosures and can change the course of a trial.

LD: When you are brought in to consult or assist in preparation for cross examinations, what is one lesson that carries over from case to case? Is there a particular type of mistake you regularly see attorneys make?

SO: Almost all crosses are unique. The most common mistakes are repeating a harmful direct without impeaching it; alternatively arguing with the witness without impeaching him.

LD: The Brass Wall, which you mentioned earlier, describes some of your trial work. Do you have another favorite book, or movie or TV show about trials or litigation that you think really gets it right?

SO: Most movies are inaccurate in their trial scenes. "The Verdict “and “Presumed Innocent” are exceptions in that they render a more realistic depiction of cross examination and how it can affect a trial’s outcome.