Photo by Dave Cross.

Sean O’Shea found it easy to separate the good guys from the bad guys. A hard-charging prosecutor in the U.S. Attorney’s Office in Brooklyn in the late 1980s, he had plenty of chances to do so, handling crimes from fraud to arson. He had come from Chicago to New York, believing it was the ideal place to learn trial law.

Experience proved him right, providing the foundation for O’Shea to emerge as one of the most experienced and respected white-collar and defense lawyers around. With 85 trials (and counting) under his belt, he has become an eminence of hard-core financial litigation, representing companies and individuals in a wide array of complex matters, often including international intrigue with sophistication and derring-do. He’s been awarded by the Department of Justice as well as the FBI, for which he serves as an instructor on trial tactics in Quantico, Va. To achieve that reputation, he circled the bases on the entire ballpark of wrongdoing – from prosecution to defense.

“When you’re a prosecutor, you indict on your schedule. You can try the case pretty much on your schedule. You have the weight of the evidence, and you choose whether to indict,” he says. “But when you’re a defense lawyer, people come to you with problems that are really, really complex and sticky. And the time frame isn’t convenient. And you have to work against what is often a formed body of evidence.”

Defense lawyers have to be able to fight that developed body of evidence and win, O’Shea says. The desire to develop those kinds of skills prompted him to leave the Eastern District, where he had become chief of the business and securities fraud unit, to start his own firm, O’Shea Partners, in 1996. Twenty years later, the firm merged with Boies Schiller & Flexner, and last year, O’Shea and two partners, Michael Petrella and Amanda Devereux, left to amplify the trial practice at Wall Street stalwart Cadwalader, Wickersham & Taft.

Lawdragon: Cadwalader seems like a great fit for your practice. How’s it going?

Sean O’Shea: It is going extremely well. I wanted a solid firm with a first-rate reputation and a lot of good people that really needed what I have to offer. Cadwalader is a capital markets powerhouse, but firm leadership also wanted to strengthen its high-end litigation, so it’s been ideal. Everyone has been very supportive, and we’re going to be hiring more people like me in the marketplace. The leaders of the firm are no-drama types, which was a selling point, and they convinced me that they needed me and were committed to continuing to build a leading litigation practice. They need even more first-tier litigation partners, and they’ve given me free rein to look out for them.

LD: Amazing. I’d love to hear more about how you got here. You weren’t always in New York, right?

SO: No. I grew up in Chicago, and my parents were both from Ireland. I was the first in my extended family to go to college. I earned my bachelor’s degree at the University of Illinois, a great public academic institution, and then I went to law school at Northwestern. When I finished, boutique firms were all the rage, and I got an offer from a very high-quality one that that had spun out of Kirkland & Ellis called Hedlund, Hunter & Lynch. Later, Latham & Watkins came along, and offered them a merger deal, which as a young associate, wasn’t necessarily the best thing for me. But I soon found myself really enjoying Latham and the people there, and I stayed for five or six years, then came to New York to the U.S. Attorney’s Office.

LD: Interesting. So why the move?

SO: New York is really the capital of white-collar crime. And that’s where I wanted to be. I wanted to do white collar; I wanted to try cases against the best lawyers in the country, and I thought that the most sophisticated stuff in the country was getting done here. And I got that opportunity.  I remember people in the U.S. Attorney’s Office used to see me sitting in the courtroom, in my limited spare time, watching the best trial lawyers in America work. And I learned from them, became friendly with them and butted heads with them, and it was a really fun place to be.

LD: Would you say that, in a way, you found your identity as a trial lawyer at the U.S. Attorney’s Office?

SO: Oh, no question. It’s funny because I’ve become the go-to guy for people in the U.S. Attorney’s Office who want to start their own practice and want to find out more about how to do it. Young lawyers ask me, “Hey, where do you go to learn to be a trial lawyer?” Without question, the U.S. Attorney’s Office is the place. I tried a ton of cases there. And I was known in the office as the trial hound; I would pick up other people’s trials, even what we called “dog” cases, and just loved every minute of it. Because you just learn so much with that jury in the box and the things you have to come up with. Look, the first few trials you do, you’re hearing your voice bounce off the walls, like, “Wow, there’s actually a jury in the box.” And “Look, Mom, I’m actually doing this.”

By the 11th or 12th trial, you’re actually in the game, and you really start to know what you’re doing in a courtroom. I was lucky that a lot of defendants took the witness stand. That enabled me to develop cross-examination skills that other prosecutors didn’t really have. Ultimately, I ended up where I wanted to be, in the white-collar unit and, eventually, heading it.

LD: Are there particular cases that served as a foundation for what you learned there and what you’ve done since?

SO: When I was the head of the unit, I did several trials against a guy who was very well known at the time, Harvey Myerson, who had started a law firm called Myerson & Kuhn.

That case came about because I was reading The Wall Street Journal one morning, and saw that Lehman Brothers had terminated its relationship with Myerson & Kuhn. And the way they disclosed it was curious to me. Usually, if they put out any kind of a statement, it’s the sort of pablum that comes out of the public relations office, but this was a little harsher: It mentioned irregularities. So I ended up looking into this. And it turned out that associates within the firm had found a double set of billing books where the hours actually recorded by lawyers were being inflated. Myerson & Kuhn turned out to be shot through with corrupt billing practices, and not just involving clients. Harvey Myerson was overbilling his partners for personal items from cigars in London to his hairpieces. We ended up convicting him twice and dismissing a third indictment, so that was one example of an exciting trial.

LD: Impressive. Cases like that give you a tremendous adrenaline rush. How about some others?

SO: Another one that I recall very well, because it had so much human drama involved, was an arson matter, and the suspects had mob connections. The chief of the organized crime section asked me to get involved because a firefighter had died in the blaze. And this was no ordinary firefighter – it was a rescue squad firefighter in New York named Tommy Williams, who had pulled people out of New York Harbor when a USAir flight trying to take off from LaGuardia airport careened into the water in September 1989. These rescue guys are real heroes. I heard the story about Tommy Williams, and I was hooked. The case turned out to have all kinds of very sticky issues, with forensics as well as expert witnesses. There was a lot of tense cross-examination. Very hard-fought trial, with good lawyers on both sides, but we ultimately won.

LD: Those are fantastic examples. When you’re in the U.S. Attorney’s Office, it’s easier to separate the good guys from the bad guys, right?

SO: Sometimes. Though over the length of my career, I’ve seen that there are sometimes shades of gray. But you’re doing important work. And if you’re really into it, you’re doing work that affects lives, affects society. You’re always a popular guy to talk to at cocktail parties.

LD: You do have the best stories.

SO: I do have some stories. It’s been years since I left the U.S. Attorney’s Office, but when Judge Edward Korman sees me at a cocktail party, he comes racing across the room and says, “Counselor, tell me more stories.” Because he remembers those trials and he says to me, “You know, those two trials are the most exciting trials I had in all my time in the bench.” And I say to him, “You know, Judge, that’s really nice to hear.” And I’ll tell you, those weren’t even the most exciting trials I’ve had.

Trials are like roller-coasters, really. They’re uncomfortable. The preparation for trial is misery. But you know, I would get that adrenaline rush of trying a case, and I’d be walking around the U.S. Attorney’s Office looking for someone who wanted to dump a trial. I was addicted to the trial drug.

LD: And then the day comes when you decide to look at the private sector. How did that happen?

SO: There are two things, really. One is that I had two children, and I was thinking about the future. What also can’t be dismissed is that you look at the trial lawyers who are really renowned and they’re almost never in the U.S. Attorney’s Office. It’s not because the trial talent isn’t there – it certainly is. But prosecutors work with the evidence. And great trial lawyers have to learn to work against the evidence. Just to pick one I really admire, Gerry Shargel, who recently retired; he and I opposed each other at trials, and I watched how he always had to work against the weight of the evidence. In terms of building out your skill set as a lawyer, doing defense work, even doing private plaintiff work, just provides that extra level of challenge that I think you’ve got to seek out if you want to be at the top tier of the profession.

LD: That is the best explanation I’ve ever heard of it. Was that when you hung out your own shingle?

SO: It was. My father thought I was crazy when I told him I wasn’t going to go back to a big law firm and that I was going to start my own practice. And I have to say the first week, it wasn’t very exciting. I was staring at the phone, starting to wonder if I had made a huge mistake. The week before, my phone had been ringing off the hook: The assistant director of the FBI needed to talk to me, the U.S. Attorney needed to talk to me. I was really in demand. And the silence, in comparison, was overwhelming. But you know, the phone starts to ring, you get involved in stuff. And one thing leads to another, and the next thing you know, you’re off to the races.

LD: Was there a particular case that confirmed that you had made the right decision? A significant matter, or one where you felt you were learning something new or going up against new people?

SO: One of my first big cases was representing a law firm, actually because of a call from Gerry Shargel, who was familiar with the expertise I had developed in law firm fraud. He got me involved in helping that firm through the crisis when its prominent founder admitted overbilling the U.S. government.

It showed me a different perspective on the good guys versus the bad guys. You start to see the other side of the equation as a defense lawyer, that people make mistakes. You start to see the humanity of those people, which maybe as a prosecutor, I wasn’t so attuned to.

LD: It is hard for prosecutors to do their jobs and dwell on the humanity, isn’t it?

SO: Definitely. But as a defense lawyer, it’s often my job to tell prosecutors that there are shades of gray. The law firm case isn’t a great example of that because I think that guy would be the first one to say, “What I did was flat wrong.” But there are many cases where I’ve been successful in talking prosecutors out of indictments.

It’s our job as defense lawyers to not just make them see humanity where they might not otherwise see it, and maybe refine their course of action a little. Good defense attorneys are skilled at painting a fuller picture. I had a case a few years back where my client – the founder of an internet gaming company – was threatened with indictment. Her co-founder represented by another prominent law firm, pleaded guilty and paid $300 million in forfeiture. Other lawyers had advised her to plead guilty as well. When I came into the case, I took a different tack both factually and legally. I developed evidence that the co-founder (who was cooperating against my client) was lying, and I developed a legal strategy that I took an appeal to the Department of Justice. That resulted in the case being dropped. And you know, those quiet successes are the ones that, as a defense lawyer, you don’t get to tout as much – no headlines, but a great victory for the client after a three-year fight.

The public glory in the defense side of the practice, of course, really goes to the people who win trials. But the clients appreciate most not having to go through the trial. So that’s one of the skills that you’ve got to learn. Another decision you face is deciding what kind of lawyer you want to be. The problem with being a criminal defense lawyer is that the statistics don’t lie: Prosecutors usually get their man. Conviction rates are better than 90 percent, and you’d end up flying the white flag of surrender constantly. I decided I wanted to be a trial lawyer, full stop, not just a criminal defense lawyer, and I started handling civil cases as well. And I had real success in the financial world.

LD: This was part of your evolution?

SO: Yes. And I think, ultimately, you want to be a lawyer that companies turn to when they’re in a world of trouble.

As an example, a couple of years back, a company – one of the country’s largest liquor distributors – was hit with a RICO lawsuit and it was really an existential threat. The plaintiff was essentially trying to put it out of business. The allegation was that my client was working with smugglers in Maryland, which is a low excise-tax state, to bring alcohol across state lines, into a high-excise tax state, New York, and sell it directly through retail establishments, harming the competitor’s sales. So I investigated the plaintiff. I learned that the competitor plaintiff had a subsidiary company in Connecticut, and my defense was not only that we weren’t doing the alleged smuggling, but in fact, the plaintiff, through a sister company, was doing it. I sued them for advancement and indemnification of my client’s legal fees, and they ended up paying for a portion of the cost of my defense of their target.

LD: Very nice.

SO: We try to always be on our toes, always be playing offense. The mentality of always preparing for trial, from day one, really helps you. The general counsel of that client, who has become a good friend, said to me, “You know, we interviewed a bunch of lawyers, Sean. And you’re the only one who came in with a plan to win on day one.”