John Gleeson, partner with Debevoise & Plimpton.

For 22 years, John Gleeson served as a federal judge in the Eastern District of New York. It was, as he puts it, “the best job in the world.”

But in 2016, Gleeson gave up his gavel and became a law firm partner at Debevoise & Plimpton where he specializes in white-collar matters, civil litigation and internal investigations.

In this interview originally published in ALM’s Legal Speak podcast, Litigation Daily editor-in-chief Jenna Greene talks with Gleeson about his career—from mob prosecutor to federal judge to law firm partner—and what he’s learned along the way. Gleeson reflects on judicial salaries, the case for term limits and the perspective he’s gained by representing private clients.

Listen to this podcast in full and other Legal Speak podcasts at or on Apple Podcasts, Google Play or Libsyn.

This conversation was edited for length and clarity.

The National Law Journal: Were there times when the responsibility weighed heavily, where in your heart you wanted to rule one way but the law required you to find otherwise?

John Gleeson: No, you know, and that I guess it wasn’t as rare as it might have been, I was a vocal proponent of sentencing reform. And I felt that our shift to determine a sentencing regime in the late ‘80s produced cataclysmic and shameful results in terms of severity of sentencing and racial disparities. So, in that one area, yes, I felt strongly that the law was wrong and said so and justified it and had written opinions and set forth my views on how the law should change. So that’s a kind of a huge exception, but as a general matter, in most cases there’s the law, and then there are facts, and a judge’s job is to make sure people have a fair opportunity to present the facts. There are competing views of the facts. It was our job to get the law right, and most of the time getting the law right wasn’t a matter of, didn’t raise issues with which one might politically disagree—it’s just a matter of figuring out what the law is. And it was challenging, but didn’t raise the kinds of issues that your question suggests or asks about.

NLJ: Do you think judges at any level should have term limits?

JG: You know, I do. I’m one of those who has come to the view given the polarization of our Supreme Court nomination and confirmation process, I do believe that term limits either ought to be enacted, or very seriously considered. I think that process that which when I was a young lawyer, looked and worked and operated fundamentally differently and produced much more moderation when it came to the Supreme Court nominees. It’s just changed in such a negative way and produced the debacles we’ve seen in recent years, including the one that’s going on as we speak. That I now think and my judicial instincts suggest I would want to hear more from all the stakeholders before deciding were I a legislator. But I think the notion of a term limit is pretty attractive. You know, all presidents get to nominate a couple of Supreme Court justices and we’re not, for lack of a better way of putting it, we’re not stuck with every justice for as long as he or she shall live. I think that’s probably a good thing. In my mind, the jury is still out a little bit on that. But that conversation needs to remain afloat.

NLJ: How has your experience on the bench do you think changed the way you practice law? Has it given you insight or perspective that you didn’t have before?

JG: It has, but I have more respect now, more understanding, of how difficult it is to practice law, than when I was on the bench. It’s not easy. As an overlay of legal and regulatory requirements and individuals and companies sometimes get into trouble because they deserve it, but they sometimes get into trouble because it’s a very complicated world. And I didn’t fully appreciate that when I just had the end result of litigation in front of me. The other thing I didn’t appreciate it is how really expensive it is for clients to engage firms, generally, including Debevoise, to engage in civil discovery. So, you know, when I was on the bench and I had a motion to dismiss in front of me, and it was kind of a toss-up, I thought, well, let’s just let them engage in discovery and I’ll see it again in a motion of summary judgment. If I had a better appreciation then for what it means for companies and individuals to engage in the discovery process, I might have on those really close calls, I might have spent more time trying to figure out whether I ought to grant the motion to dismiss. So that’s just a part of growing up. If some president comes along and I get nominated to the bench and I get confirmed again, I’ll be a better judge.

NLJ: Were there things that as a judge with lawyers appearing before you that you wish they did or didn’t do? Any sort of tips for lawyers on how to be more effective before a judge?

JG: Well, you know, certainly on the civil side, like most things in life, preparation is what counts the most. And you never go to court without knowing your case, your facts, your law, inside out. If you demand of yourself that you know the answer to every single question that can be posed to you, it can be kind of harrowing to get ready. But it pays off. On the criminal side, you know the shift from mandatory sentencing guidelines, to advisory guidelines, place in very stark relief the importance of especially criminal defense lawyers, to know everything they can to know their client—to humanize their client—judges now have more discretion before they had 2005 to sentence the whole person, not just a part of the person who committed the crime. To this day, to the point I left the bench, I don’t think criminal defense lawyers availed themselves of that opportunity to do better by their client than they could have, than they could have previously. I found that to be a system-wide deficiency.

NLJ: I think people tend to view being a federal judge as maybe the brass ring of the profession? Do you still feel that way? Is it the best job as a lawyer do you think?

JG: Short of being center fielder for the Yankees, or a lead singer in a rock and roll band, it’s the best job in the world, not just in the profession. Being a federal district judge, not an appellate judge—I wouldn’t mind trying out being a Supreme Court justice—but in terms of lower court federal judges, federal district judge is the best job in the profession. And I think, honest to goodness, it’s the best job in the world. It’s so interesting and important and gratifying and it imbues you with the responsibility of doing justice for people, and that’s why it is the brass ring.

Interview transcribed by NLJ managing editor Mark Bauer.