Welcome to Original Jurisdiction, the latest legal publication by me, David Lat. You can learn more about Original Jurisdiction by reading its About page, and you can email me at [email protected]. This is a reader-supported publication; you can subscribe by clicking here.
How are the federal courts faring during these tumultuous times? I thought it would be worthwhile to discuss this important subject with a former federal judge: someone who understands the judicial role well but could speak more freely than a sitting judge, liberated from the strictures of the bench.
Meet Judge Nancy Gertner (Ret.), who served as a U.S. District Judge for the District of Massachusetts from 1994 until 2011. I knew that Judge Gertner would be a lively and insightful interviewee—based not only on her extensive commentary on recent events, reflected in media interviews and op-eds, but on my personal experience. During law school, I took a year-long course on federal sentencing with her, and she was one of my favorite professors.
When I was her student, we disagreed on a lot: I was severely conservative back then, and Judge Gertner was, well, not. But I always appreciated and enjoyed hearing her views—so it was a pleasure hearing them once again, some 25 years later, in what turned out to be an excellent conversation.
Show Notes:
* Nancy Gertner, author website
* Nancy Gertner bio, Harvard Law School
* In Defense of Women: Memoirs of an Unrepentant Advocate, Amazon
Prefer reading to listening? For paid subscribers, a transcript of the entire episode appears below.
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Three quick notes about this transcript. First, it has been cleaned up from the audio in ways that don’t alter substance—e.g., by deleting verbal filler or adding a word here or there to clarify meaning. Second, my interviewee has not reviewed this transcript, and any errors are mine. Third, because of length constraints, this newsletter may be truncated in email; to view the entire post, simply click on “View entire message” in your email app.
David Lat: Welcome to the Original Jurisdiction podcast. I’m your host, David Lat, author of a Substack newsletter about law and the legal profession also named Original Jurisdiction, which you can read and subscribe to at davidlat.substack.com. You’re listening to the eighty-fifth episode of this podcast, recorded on Monday, November 3.
Thanks to this podcast’s sponsor, NexFirm. NexFirm helps Biglaw attorneys become founding partners. To learn more about how NexFirm can help you launch your firm, call 212-292-1000 or email [email protected]. Want to know who the guest will be for the next Original Jurisdiction podcast? Follow NexFirm on LinkedIn for a preview.
Many of my guests have been friends of mine for a long time—and that’s the case for today’s. I’ve known Judge Nancy Gertner for more than 25 years, dating back to when I took a full-year course on federal sentencing from her and the late Professor Dan Freed at Yale Law School. She was a great teacher, and although we didn’t always agree—she was a professor who let students have their own opinions—I always admired her intellect and appreciated her insights.
Judge Gertner is herself a graduate of Yale Law School—where she met, among other future luminaries, Bill and Hillary Clinton. After a fascinating career in private practice as a litigator and trial lawyer handling an incredibly diverse array of cases, Judge Gertner was appointed to serve as a U.S. District Judge for the District of Massachusetts in 1994, by President Clinton. She retired from the bench in 2011, but she is definitely not retired: she writes opinion pieces for outlets such as The New York Times and The Boston Globe, litigates and consults on cases, and trains judges and litigators. She’s also working on a book called Incomplete Sentences, telling the stories of the people she sentenced over 17 years on the bench. Her autobiography, In Defense of Women: Memoirs of an Unrepentant Advocate, was published in 2011. Without further ado, here’s my conversation with Judge Nancy Gertner.
Judge, thank you so much for joining me.
Nancy Gertner: Thank you for inviting me. This is wonderful.
DL: So it’s funny: I’ve been wanting to have you on this podcast in a sense before it existed, because you and I worked on a podcast pilot. It ended up not getting picked up, but perhaps they have some regrets over that, because legal issues have just blown up since then.
NG: I remember that. I think it was just a question of scheduling, and it was before Trump, so we were talking about much more sophisticated, superficial things, as opposed to the rule of law and the demise of the Constitution.
DL: And we will get to those topics. But to start off my podcast in the traditional way, let’s go back to the beginning. I believe we are both native New Yorkers?
NG: Yes, that’s right. I was born on the Lower East Side of Manhattan, in an apartment that I think now is a tenement museum, and then we moved to Flushing, Queens, where I lived into my early 20s.
DL: So it’s interesting—I actually spent some time as a child in that area. What was your upbringing like? What did your parents do?
NG: My father owned a linoleum store, or as we used to call it, “tile,” and my mother was a homemaker. My mother worked at home. We were lower class on the Lower East Side and maybe made it to lower-middle. My parents were very conservative, in the sense they didn’t know exactly what to do with a girl who was a bit of a radical. Neither I nor my sister was precisely what they anticipated. So I got to Barnard for college only because my sister had a conniption fit when he wouldn’t pay for college for her—she’s my older sister—he was not about to pay for college. If we were boys, we would’ve had college paid for.
In a sense, they skipped a generation. They were actually much more traditional than their peers were. My father was Orthodox when he grew up; my mother was somewhat Orthodox Jewish. My father couldn’t speak English until the second grade. So they came from a very insular environment, and in one sense, he escaped that environment when he wanted to play ball on Saturdays. So that was actually the motivation for moving to Queens: to get away from the Lower East Side, where everyone would know that he wasn’t in temple on Saturday. We used to have interesting discussions, where I’d say to him that my rebellion was a version of his: he didn’t want to go to temple on Saturdays, and I was marching against the war. He didn’t see the equivalence, but somehow I did.
There’s actually a funny story to tell about sort of exactly the distance between how I was raised and my life. After I graduated from Yale Law School, with all sorts of honors and stuff, and was on my way to clerk for a judge, my mother and I had this huge fight in the kitchen of our apartment. What was the fight about? Sadie wanted me to take the Triborough Bridge toll taker’s test, “just in case.” “You never know,” she said. I couldn’t persuade her that it really wasn’t necessary. She passed away before I became a judge, and I told this story at my swearing-in, and I said that she just didn’t understand. I said, “Now I have to talk to my mother for a minute; forgive me for a moment.” And I looked up at the rafters and I said, “Ma, at last: a government job!” So that is sort of the measure of where I started. My mother didn’t finish high school, my father had maybe a semester of college—but that wasn’t what girls did.
DL: So were you then a first-generation professional or a first-generation college graduate?
NG: Both—my sister and I were both, first-generation college graduates and first-generation professionals. When people talk about Jewish backgrounds, they’re very different from one another, and since my grandparents came from Eastern European shtetls, it’s not clear to me that they—except for one grandfather—were even literate. So it was a very different background.
DL: You mentioned that you did go to Yale Law School, and of course we connected there years later, when I was your student. But what led you to go to law school in the first place? Clearly your parents were not encouraging your professional ambitions.
NG: One is, I love to speak. My husband kids me now and says that I’ve never met a microphone I didn’t like. I had thought for a moment of acting—musical comedy, in fact. But it was 1967, and the anti-war movement, a nascent women’s movement, and the civil rights movement were all rising around me, and I wanted to be in the world. And the other thing was that I didn’t want to do anything that women do. Actually, musical comedy was something that would’ve been okay and normal for women, but I didn’t want to do anything that women typically do. So that was the choice of law. It was more like the choice of law professor than law, but that changed over time.
DL: So did you go straight from Barnard to Yale Law School?
NG: Well, I went from Barnard to Yale graduate school in political science because as I said, I’ve always had an academic and a practical side, and so I thought briefly that I wanted to get a Ph.D. I still do, actually—I’m going to work on that after these books are finished.
DL: Did you then think that you wanted to be a law professor when you started at YLS? I guess by that point you already had a master’s degree under your belt?
NG: I thought I wanted to be a law professor, that’s right. I did not think I wanted to practice law. Yale at that time, like most law schools, had no practical clinical courses. I don’t think I ever set foot in a courtroom or a courthouse, except to demonstrate on the outside of it. And the only thing that started me in practice was that I thought I should do at least two or three years of practice before I went back into the academy, before I went back into the library. Twenty-four years later, I obviously made a different decision.
DL: So you were at YLS during a very interesting time, and some of the law school’s most famous alumni passed through its halls around that period. So tell us about some of the people you either met or overlapped with at YLS during your time there.
NG: Hillary Clinton was one of my best friends. I knew Bill, but I didn’t like him.
DL: Hmmm….
NG: She was one of my best friends. There were 20 women in my class, which was the class of ‘71. The year before, there had only been eight. I think we got up to 21—a rumor had it that it was up to 21 because men whose numbers were drafted couldn’t go to school, and so suddenly they had to fill their class with this lesser entity known as women. It was still a very small number out of, I think, what was the size of the opening class… 165? Very small. So we knew each other very, very well. And Hillary and I were the only ones, I think, who had no boyfriends at the time, though that changed.
DL: I think you may have either just missed or briefly overlapped with either Justice Thomas or Justice Alito?
NG: They’re younger than I am, so I think they came after.
DL: And that would be also true of Justice Sotomayor then as well?
NG: Absolutely. She became a friend because when I was on the bench, I actually sat with the Second Circuit, and we had great times together. But she was younger than I was, so I didn’t know her in law school, and by the time she was in law school, there were more women. In the middle of, I guess, my first year at Yale Law School, was the first year that Yale College went coed. So it was, in my view, an enormously exciting time, because we felt like we were inventing law. We were inventing something entirely new. We had the first “women in the law” course, one of the first such courses in the country, and I think we were borderline obnoxious. It’s a little bit like the debates today, which is that no one could speak right—you were correcting everyone with respect to the way they were describing women—but it was enormously creative and exciting.
DL: So I’m gathering you enjoyed law school, then?
NG: I loved law school. Still, when I was in law school, I still had my feet in graduate school, so I believe that I took law and sociology for three years, mostly. In other words, I was going through law school as if I were still in graduate school, and it was so bad that when I decided to go into practice—and this is an absolutely true story—I thought that dying intestate was a disease. We were taking the bar exam, and I did not know what they were talking about.
DL: So tell us, then, what did lead you to shift gears? You mentioned you clerked, and you mentioned you wanted to practice for a few years—but you did practice for more than a few years.
NG: Right. I talk to students about this all the time, about sort of the fortuities that you need to grab onto that you absolutely did not plan. So I wind up at a small civil-rights firm, Harvey Silverglate and Norman Zalkind’s firm. I wind up in a small civil-rights firm because I couldn’t get a job anywhere else in Boston. I was looking in Boston or San Francisco, and what other women my age were encountering, I encountered, which is literally people who told me that I would never succeed as a lawyer, certainly not as a litigator. So you have to understand, this is 1971. I should say, as a footnote, that I have a file of everyone who said that to me. People know that I have that file; it’s called “Sexist Tidbits.” And so I used to decide whether I should recuse myself when someone in that file appeared before me, but I decided it was just too far.
So it was a small civil-rights firm, and they were doing draft cases, they were doing civil-rights cases of all different kinds, and they were doing criminal cases. After a year, the partnership between Norman Zalkind and Harvey Silverglate broke up, and Harvey made me his partner, now an equal partner after a year of practice.
Shortly after that, I got a case that changed my career in so many ways, which is I wound up representing Susan Saxe. Susan Saxe was one of five individuals who participated in robberies to get money for the anti-war movement. She was probably five years younger than I was. In the case of the robbery that she participated in, a police officer was killed. She was charged with felony murder. She went underground for five years; the other woman went underground for 20 years.
Susan wanted me to represent her, not because she had any sense that I was any good—it’s really quite wonderful—she wanted me to represent her because she figured her case was hopeless. And her case was hopeless because the three men involved in the robbery either fled or were immediately convicted, so her case seemed to be hopeless. And she was an extraordinarily principled woman: she said that in her last moment on the stage—she figured that she’d be convicted and get life—she wanted to be represented by a woman. And I was it. There was another woman in town who was a public defender, but I was literally the only private lawyer. I wrote about the case in my book, In Defense of Women, and to Harvey Silvergate’s credit, even though the case was virtually no money, he said, “If you want to do it, do it.”
Because I didn’t know what I was doing—and I literally didn’t know what I was doing—I researched every inch of everything in the case. So we had jury research and careful jury selection, hiring people to do jury selection. I challenged the felony-murder rule (this was now 1970). If there was any evidentiary issue, I would not only do the legal research, but talk to social psychologists about what made sense to do. To make a long story short, it took about two years to litigate the case, and it’s all that I did.
And the government’s case was winding down, and it seemed to be not as strong as we thought it was—because, ironically, nobody noticed the woman in the bank. Nobody was noticing women in general; nobody was noticing women in the bank. So their case was much weaker than we thought, except there were two things, two letters that Susan had written: one to her father, and one to her rabbi. The one to her father said, “By the time you get this letter, you’ll know what your little girl is doing.” The one to her rabbi said basically the same thing. In effect, these were confessions. Both had been turned over to the FBI.
So the case is winding down, not very strong. These letters have not yet been introduced. Meanwhile, The Boston Globe is reporting that all these anti-war activists were coming into town, and Gertner, who no one ever heard of, was going to try the Vietnam War. The defense will be, “She robbed a bank to fight the Vietnam War.” She robbed a bank in order to get money to oppose the Vietnam War, and the Vietnam War was illegitimate, etc. We were going to try the Vietnam War.
There was no way in hell I was going to do that. But nobody had ever heard of me, so they believed anything. The government decided to rest before the letters came in, anticipating that our defense would be a collection of individuals who were going to challenge the Vietnam War. The day that the government rested without putting in those two letters, I rested my case, and the case went immediately to the jury. I’m told that I was so nervous when I said “the defense rests” that I sounded like Minnie Mouse.
The upshot of that, however, was that the jury was 9-3 for acquittal on the first day, 10-2 for acquittal on the second day, and then 11-1 for acquittal—and there it stopped. It was a hung jury. But it essentially made my career. I had first the experience of pouring my heart into a case and saving someone’s life, which was like nothing I’d ever felt before, which was better than the library. It also put my name out there. I was no longer, “Who is she?” I suddenly could take any kind of case I wanted to take. And so I was addicted to trials from then until the time I became a judge.
DL: Fill us in on what happened later to your client, just her ultimate arc.
NG: She wound up getting eight years in prison instead of life. She had already gotten eight years because of a prior robbery in Philadelphia, so there was no way that we were going to affect that. She had pleaded guilty to that. She went on to live a very principled life. She’s actually quite religious. She works in the very sort of left Jewish groups. We are in touch—I’m in touch with almost everyone that I’ve ever known—because it had been a life-changing experience for me. We were four years apart. Her background, though she was more middle-class, was very similar to my own. Her mother used to call me at night about what Susan should wear. So our lives were very much intertwined. And so she was out of jail after eight years, and she has a family and is doing fine.
DL: That’s really a remarkable result, because people have to understand what defense lawyers are up against. It’s often very challenging, and a victory is often a situation where your client doesn’t serve life, for example, or doesn’t, God forbid, get the death penalty. So it’s really interesting that the Saxe case—as you talk about in your wonderful memoir—really did launch your career to the next level. And you wound up handling a number of other cases that you could say were adjacent or thematically related to Saxe’s case. Maybe you can talk a little bit about some of those.
NG: The women’s movement was roaring at this time, and so a woman lawyer who was active and spoke out and talked about women’s issues invariably got women’s cases. So on the criminal side, I did one of the first, I think it was the first, battered woman syndrome case, as a defense to murder. On the civil side, I had a very robust employment-discrimination practice, dealing with sexual harassment, dealing with racial discrimination. I essentially did whatever I wanted to do. That’s what my students don’t always understand: I don’t remember ever looking for a lucrative case. I would take what was interesting and fun to me, and money followed. I can’t describe it any other way.
These cases—you wound up getting paid, but I did what I thought was meaningful. But it wasn’t just women’s rights issues, and it wasn’t just criminal defense. We represented white-collar criminal defendants. We represented Boston Mayor Kevin White’s second-in-command, Ted Anzalone, also successfully. I did stockholder derivative suits, because someone referred them to me. To some degree the Saxe case, and maybe it was also the time—I did not understand the law to require specialization in the way that it does now. So I could do a felony-murder case on Monday and sue Mayor Lynch on Friday and sue Gulf Oil on Monday, and it wouldn’t even occur to me that there was an issue. It was not the same kind of specialization, and I certainly wasn’t about to specialize.
DL: You anticipated my next comment, which is that when someone reads your memoir, they read about a career that’s very hard to replicate in this day and age. For whatever reason, today people specialize. They specialize at earlier points in their careers. Clients want somebody who holds himself out as a specialist in white-collar crime, or a specialist in dealing with defendants who invoke battered woman syndrome, or what have you. And so I think your career… you kind of had a luxury, in a way.
NG: I also think that the costs of entry were lower. It was Harvey Silverglate and me, and maybe four or five other lawyers. I was single until I was 39, so I had no family pressures to speak of. And I think that, yes, the profession was different. Now employment discrimination cases involve prodigious amounts of e-discovery. So even a little case has e-discovery, and that’s partly because there’s a generation—you’re a part of it—that lived online. And so suddenly, what otherwise would have been discussions over the back fence are now text messages.
So I do think it’s different—although maybe this is a comment that only someone who is as old as I am can make—I wish that people would forget the money for a while. When I was on the bench, you’d get a pro se case that was incredibly interesting, challenging prison conditions or challenging some employment issue that had never been challenged before. It was pro se, and I would get on the phone and try to find someone to represent this person. And I can’t tell you how difficult it was. These were not necessarily big cases. The big firms might want to get some publicity from it. But there was not a sense of individuals who were going to do it just, “Boy, I’ve never done a case like this—let me try—and boy, this is important to do.” Now, that may be different today in the Trump administration, because there’s a huge number of lawyers that are doing immigration cases. But the day-to-day discrimination cases, even abortion cases, it was not the same kind of support.
DL: I feel in some ways you were ahead of your time, because your career as a litigator played out in boutiques, and I feel that today, many lawyers who handle high-profile cases like yours work at large firms. Why did you not go to a large firm, either from YLS or if there were issues, for example, of discrimination, you must have had opportunities to lateral into such a firm later, if you had wanted to?
NG: Well, certainly at the beginning nobody wanted me. It didn’t matter how well I had done. Me and Ruth Ginsburg were on the streets looking for jobs. So that was one thing. I wound up, for the last four years of my practice before I became a judge, working in a firm called Dwyer Collora & Gertner. It was more of a boutique, white-collar firm. But I wasn’t interested in the big firms because I didn’t want anyone to tell me what to do. I didn’t want anyone to say, “Don’t write this op-ed because you’ll piss off my clients.” I faced the same kind of issue when I left the bench. I could have an office, and sort of float into client conferences from time to time, but I did not want to be in a setting in which anyone told me what to do. It was true then; it certainly is true now.
DL: So you did end up in another setting where, for the most part, you weren’t told what to do: namely, you became a federal judge. And I suppose the First Circuit could from time to time tell you what to do, but….
NG: But they were always wrong.
DL: Yes, I do remember that when you were my professor, you would offer your thoughts on appellate rulings. But how did you—given the kind of career you had, especially—become a federal judge? Because let me be honest, I think that somebody with your type of engagement in hot-button issues today would have a challenging time. Republican senators would grandstand about you coming up with excuses for women murderers, or what have you. Did you have a rough confirmation process?
NG: I did. So I’m up for the bench in 1993. This is under Bill Clinton, and I’m told—I never confirmed this—that when Senator Kennedy…. When I met Senator Kennedy, I thought I didn’t have a prayer of becoming a judge. I put my name in because I knew the Clintons, and everybody I knew was getting a job in the government. I had not thought about being a judge. I had not prepared. I had not structured my career to be a judge. But everyone I knew was going into the government, and I thought if there ever was a time, this would be it. So I apply. Someday, someone should emboss my application, because the application was quite hysterical. I put in every article that I had written calling for access to reproductive technologies to gay people. It was something to behold.
Kennedy was at the tail end of his career, and he was determined to put someone like me on the bench. I’m not sure that anyone else would have done that. I’m told (and this isn’t confirmed) that when he talked to Bill and Hillary about me, they of course knew me—Hillary and I had been close friends—but they knew me to be that radical friend of theirs from Yale Law School. There had been 24 years in between, but still. And I’m told that what was said was, “She’s terrific. But if there’s a problem, she’s yours.” But Kennedy was really determined.
The week before my hearing before the Senate, I had gotten letters from everyone who had ever opposed me. Every prosecutor. I can’t remember anyone who had said no. Bill Weld wrote a letter. Bob Mueller, who had opposed me in cases, wrote a letter. But as I think oftentimes happens with women, there was an article in The Boston Herald the day before my hearing, in which the writer compared me to Lorena Bobbitt. Your listeners may not know this, but he said, “Gertner will do to justice, with her gavel, what Lorena did to her husband, with a kitchen knife.” Do we have to explain that any more?
DL: They can Google it or ask ChatGPT. I’m old enough to know about Lorena Bobbitt.
NG: Right. So it’s just at the tail edge of the presentation, that was always what the caricature would be. But Kennedy was masterful. There were numbers of us who were all up at the same time. Everyone else got through except me. I’m told that that article really was the basis for Senator Jesse Helms’s opposition to me. And then Senator Kennedy called us one day and said, “Tomorrow you’re going to read something, but don’t worry, I’ll take care of it.” And the Boston Globe headline says, “Kennedy Votes For Helms’s School-Prayer Amendment.” And he called us and said, “We’ll take care of it in committee.” And then we get a call from him—my husband took the call—Kennedy, affecting Helms’s accent, said, ‘Senator, you’ve got your judge.’ We didn’t even understand what the hell he said, between his Boston accent and imitating Helms; we had no idea what he said. But that then was confirmed.
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So turning to your time as a judge, how would you describe that period, in a nutshell? The job did come with certain restrictions. Did you enjoy it, notwithstanding the restrictions?
NG: I candidly was not sure that I would last beyond five years, for a couple of reasons. One was, I got on the bench in 1994, when the sentencing guidelines were mandatory, when what we taught you in my sentencing class was not happening, which is that judges would depart from the guidelines and the Sentencing Commission, when enough of us would depart, would begin to change the guidelines, and there’d be a feedback loop. There was no feedback loop. If you departed, you were reversed. And actually the genesis of the book I’m writing now came from this period. As far as I was concerned, I was being unfair. As I later said, my sentences were unfair, unjust, and disproportionate—and there was nothing I could do about it. So I was not sure that I was going to last beyond five years.
In addition, there were some high-profile criminal trials going on with lawyers that I knew that I probably would’ve been a part of if I had been practicing. And I hungered to do that, to go back and be a litigator. The course at Yale Law School that you were a part of saved me. And it saved me because, certainly with respect to the sentencing, it turned what seemed like a formula into an intellectual discussion in which there was wiggle room and the ability to come up with other approaches. In other words, we were taught that this was a formula, and you don’t depart from the formula, and that’s it. The class came up with creative issues and creative understandings, which made an enormous difference to my judging.
So I started to write; I started to write opinions. Even if the opinion says there’s nothing I can do about it, I would write opinions in which I say, “I can’t depart because of this woman’s status as a single mother because the guidelines said only extraordinary family circumstances can justify a departure, and this wasn’t extraordinary. That makes no sense.” And I began to write this in my opinions, I began to write this in scholarly writings, and that made all the difference in the world. And sometimes I was reversed, and sometimes I was not. But it enabled me to figure out how to push back against a system which I found to be palpably unfair. So I figured out how to be me in this job—and that was enormously helpful.
DL: And I know how much and how deeply you cared about sentencing because of the class in which I actually wound up writing one of my two capstone papers at Yale.
NG: To your listeners, I still have that paper.
DL: You must be quite a pack rat!
NG: I can change the grade at any time….
DL: Well, I hope you’ve enjoyed your time today, Judge, and will keep the grade that way!
But let me ask you: now that the guidelines are advisory, do you view that as a step forward from your time on the bench? Perhaps you would still be a judge if they were advisory? I don’t know.
NG: No, they became advisory in 2005, and I didn’t leave until 2011. Yes, that was enormously helpful: you could choose what you thought was a fair sentence, so it’s very advisory now. But I don’t think I would’ve stayed longer, because of two reasons.
By the time I hit 65, I wanted another act. I wanted another round. I thought I had done all that I could do as a judge, and I wanted to try something different. And Martha Minow of Harvard Law School made me an offer I couldn’t refuse, which was to teach at Harvard. So that was one. It also, candidly, was that there was no longevity in my family, and so when I turned 65, I wasn’t sure what was going to happen. So I did want to try something new. But I’m still here.
DL: Yep—definitely, and very active. I always chuckle when I see “Ret.,” the abbreviation for “retired,” in your email signature, because you do not seem very retired to me. Tell us what you are up to today.
NG: Well, first I have this book that I’ve been writing for several years, called Incomplete Sentences. And so what this book started to be about was the men and women that I sentenced, and how unfair it was, and what I thought we should have done. Then one day I got a message from a man by the name of Darryl Green, and it says, “Is this Nancy Gertner? If it is, I think about you all the time. I hope you’re well. I’m well. I’m an iron worker. I have a family. I’ve written books. You probably don’t remember me.” This was a Facebook message. I knew exactly who he was. He was a man who had faced the death penalty in my court, and I acquitted him. And he was then tried in state court, and acquitted again. So I knew exactly who he was, and I decided to write back.
So I wrote back and said, “I know who you are. Do you want to meet?” That started a series of meetings that I’ve had with the men I’ve sentenced over the course of the 17-year career that I had as a judge. Why has it taken me this long to write? First, because these have been incredibly moving and difficult discussions. Second, because I wanted the book to be honest about what I knew about them and what a difference maybe this information would make. It is extremely difficult, David, to be honest about judging, particularly in these days when judges are parodied. So if I talk about how I wanted to exercise some leniency in a case, I understand that this can be parodied—and I don’t want it to be, but I want to be honest.
So for example, in one case, there would be cooperators in the case who’d get up and testify that the individual who was charged with only X amount of drugs was actually involved with much more than that. And you knew that if you believed the witness, the sentence would be doubled, even though you thought that didn’t make any sense. This was really just mostly how long the cops were on the corner watching the drug deals. It didn’t make the guy who was dealing drugs on a bicycle any more culpable than the guy who was doing massive quantities into the country.
So I would struggle with, “Do I really believe this man, the witness who’s upping the quantity?” And the kinds of exercises I would go through to make sure that I wasn’t making a decision because I didn’t like the implications of the decision and it was what I was really feeling. So it’s not been easy to write, and it’s taken me a very long time. The other side of the coin is they’re also incredibly honest with me, and sometimes I don’t want to know what they’re saying. Not like a sociologist who could say, “Oh, that’s an interesting fact, I’ll put it in.” It’s like, “Oh no, I don’t want to know that.”
DL: Wow. The book sounds amazing; I can’t wait to read it. When is it estimated to come out?
NG: Well, I’m finishing it probably at the end of this year. I’ve rewritten it about five times. And my hope would be sometime next year. So yeah, it was organic. It’s what I wanted to write from the minute I left the bench. And it covers the guideline period when it was lunacy to follow the guidelines, to a period when it was much more flexible, but the guidelines still disfavored considering things like addiction and trauma and adverse childhood experiences, which really defined many of the people I was sentencing. So it’s a cri de cœur, as they say, which has not been easy to write.
DL: Speaking of cri de cœurs, and speaking of difficult things, it’s difficult to write about judging, but I think we also have alluded already to how difficult it is to engage in judging in 2025. What general thoughts would you have about being a federal judge in 2025? I know you are no longer a federal judge. But if you were still on the bench or when you talk to your former colleagues, what is it like on the ground right now?
NG: It’s nothing like when I was a judge. In fact, the first thing that happened when I left the bench is I wrote an article in which I said—this is in 2011—that the only pressure I had felt in my 17 years on the bench was to duck, avoid, and evade, waiver, statute of limitations. Well, all of a sudden, you now have judges who at least since January are dealing with emergencies that they can’t turn their eyes away from, judges issuing rulings at 1 a.m., judges writing 60-page decisions on an emergency basis, because what the president is doing is literally unprecedented. The courts are being asked to look at issues that have never been addressed before, because no one has ever tried to do the things that he’s doing. And they have almost overwhelmingly met the moment. It doesn’t matter whether you’re ruling for the government or against the government; they are taking these challenges enormously seriously. They’re putting in the time.
I had two clerks, maybe some judges have three, but it’s a prodigious amount of work. Whereas everyone complained about the Trump prosecutions proceeding so slowly, judges have been working expeditiously on these challenges, and under circumstances that I never faced, which is threats the likes of which I have never seen. One judge literally played for me the kinds of voice messages that he got after a decision that he issued. So they’re doing it under circumstances that we never had to face. And it’s not just the disgruntled public talking; it’s also our fellow Yale Law alum, JD Vance, talking about rogue judges. That’s a level of delegitimization that I just don’t think anyone ever had to deal with before. So they’re being challenged in ways that no other judges have, and they are being threatened in a way that no judges have.
On the other hand, I wish I were on the bench.
DL: Interesting, because I was going to ask you that. If you were to give lower-court judges a grade, to put you back in professor mode, on their performance since January 2025, what grade would you give the lower courts?
NG: Oh, I would give them an A. I would give them an A. It doesn’t matter which way they have come out: decision after decision has been thoughtful and careful. They put in the time. Again, this is not a commentary on what direction they have gone in, but it’s a commentary on meeting the moment. And so now these are judges who are getting emergency orders, emergency cases, in the midst of an already busy docket. It has really been extraordinary. The district courts have; the courts of appeals have. I’ve left out another court….
DL: We’ll get to that in a minute. But I’m curious: you were on the District of Massachusetts, which has been a real center of activity because many groups file there. As we’re recording this, there is the SNAP benefits, federal food assistance litigation playing out there [before Judge Indira Talwani, with another case before Chief Judge John McConnell of Rhode Island]. So it’s really just ground zero for a lot of these challenges. But you alluded to the Supreme Court, and I was going to ask you—even before you did—what grade would you give them?
NG: Failed. The debate about the shadow docket, which you write about and I write about, in which Justice Kavanaugh thinks, “we’re doing fine making interim orders, and therefore it’s okay that there’s even a precedential value to our interim orders, and thank you very much district court judges for what you’re doing, but we’ll be the ones to resolve these issues”—I mean, they’re resolving these issues in the most perfunctory manner possible.
In the tariff case, for example, which is going to be argued on Wednesday, the Court has expedited briefing and expedited oral argument. They could do that with the emergency docket, but they are preferring to hide behind this very perfunctory decision making. I’m not sure why—maybe to keep their options open? Justice Barrett talks about how if it’s going to be a hasty decision, you want to make sure that it’s not written in stone. But of course then the cases dealing with independent commissions, in which you are allowing the government, allowing the president, to fire people on independent commissions—these cases are effectively overruling Humphrey’s Executor, in the most ridiculous setting. So the Court is not meeting the moment. It was stunning that the Court decided in the birthright-citizenship case to be concerned about nationwide injunctions, when in fact nationwide injunctions had been challenged throughout the Biden administration, and they just decided not to address the issue then.
Now, I have a lot to say about Justice Kavanaugh’s dressing-down of Judge [William] Young [of the District of Massachusetts]….
DL: Or Justice Gorsuch, joined by Justice Kavanaugh.
NG: That’s right, it was Justice Gorsuch. It was stunningly inappropriate, stunningly inappropriate, undermines the district courts that frankly are doing much better than the Supreme Court in meeting the moment. The whole concept of defying the Supreme Court—defying a Supreme Court order, a three-paragraph, shadow-docket order—is preposterous. So whereas the district courts and the courts of appeals are meeting the moment, I do not think the Supreme Court is. And that’s not even going into the merits of the immunity decision, which I think has let loose a lawless presidency that is even more lawless than it might otherwise be. So yes, that failed.
DL: I do want to highlight for my readers that in addition to your books and your speaking, you do write quite frequently on these issues in the popular press. I’ve seen your work in The New York Times and The Boston Globe. I know you’re working on a longer essay about the rule of law in the age of Trump, so people should look out for that. Of all the things that you worry about right now when it comes to the rule of law, what worries you the most?
NG: I worry that the president will ignore and disobey a Supreme Court order. I think a lot about the judges that are dealing with orders that the government is not obeying, and people are impatient that they’re not immediately moving to contempt. And one gets the sense with the lower courts that they are inching up to the moment of contempt, but do not want to get there because it would be a stunning moment when you hold the government in contempt. I think the Supreme Court is doing the same thing. I initially believed that the Supreme Court was withholding an anti-Trump decision, frankly, for fear that he would not obey it, and they were waiting till it mattered. I now am no longer certain of that, because there have been rulings that made no sense as far as I’m concerned. But my point was that they, like the lower courts, were holding back rather than saying, “Government, you must do X,” for fear that the government would say, “Go pound sand.” And that’s what I fear, because when that happens, it will be even more of a constitutional crisis than we’re in now. It’ll be a constitutional confrontation, the likes of which we haven’t seen. So that’s what I worry about.
DL: Picking up on what you just said, here’s something that I posed to one of my prior guests, Pam Karlan. Let’s say you’re right that the Supreme Court doesn’t want to draw this line in the sand because of a fear that Trump, being Trump, will cross it. Why is that not prudential? Why is that not the right thing? And why is it not right for the Supreme Court to husband its political capital for the real moment?
Say Trump—I know he said lately he’s not going to—but say Trump attempts to run for a third term, and some case goes up to the Supreme Court on that basis, and the Court needs to be able to speak in a strong, unified, powerful voice. Or maybe it’ll be a birthright-citizenship case, if he says, when they get to the merits of that, “Well, that’s really nice that you think that there’s such a thing as birthright citizenship, but I don’t, and now stop me.” Why is it not wise for the Supreme Court to protect itself, until this moment when it needs to come forward and protect all of us?
NG: First, the question is whether that is in fact what they are doing, and as I said, there were two schools of thought on this. One school of thought was that is what they were doing, and particularly doing it in an emergency, fuzzy, not really precedential way, until suddenly you’re at the edge of the cliff, and you have to either say taking away birthright citizenship was unconstitutional, or tariffs, you can’t do the tariffs the way you want to do the tariffs. I mean, they’re husbanding—I like the way you put it, husbanding—their political capital, until that moment. I’m not sure that that’s true. I think we’ll know that if in fact the decisions that are coming down the pike, they actually decide against Trump—notably the tariff ones, notably birthright citizenship. I’m just not sure that that’s true.
And besides, David, there are some of these cases they did not have to take. The shadow docket was about where plaintiffs were saying it is an emergency to lay people off or fire people. Irreparable harm is on the plaintiff’s side, whereas the government otherwise would just continue to do that which it has been doing. There’s no harm to it continuing that. USAID—you don’t have a right to dismantle the USAID. The harm is on the side of the dismantling, not having you do that which you have already done and could do through Congress, if you wanted to. They didn’t have to take those cases. So your comment about husbanding political capital is a good comment, but those cases could have remained as they were in the district courts with whatever the courts of appeals did, and they could do what previous courts have done, which is wait for the issues to percolate longer.
The big one for me, too, is the voting rights case. If they decide the voting rights case in January or February or March, if they rush it through, I will say then it’s clear they’re in the tank for Trump, because the only reason to get that decision out the door is for the 2026 election. So I want to believe that they are husbanding their political capital, but I’m not sure that if that’s true, that we would’ve seen this pattern. But the proof will be with the voting rights case, with birthright citizenship, with the tariffs.
DL: Well, it will be very interesting to see what happens in those cases. But let us now turn to my speed round. These are four questions that are the same for all my guests, and my first question is, what do you like the least about the law? And this can either be the practice of law or law as an abstract system of governance.
NG: The practice of law. I do some litigation; I’m in two cases. When I was a judge, I used to laugh at people who said incivility was the most significant problem in the law. I thought there were lots of other more significant problems. I’ve come now to see how incredibly nasty the practice of law is. So yes—and that is no fun.
DL: My second question is, what would you be if you were not a lawyer/judge/retired judge?
NG: Musical comedy star, clearly! No question about it.
DL: There are some judges—Judge Fred Block in the Eastern District of New York, Judge Jed Rakoff in the Southern District of New York—who do these little musical stylings for their court shows. I don’t know if you’ve ever tried that?
NG: We used to do Shakespeare, Shakespeare readings, and I loved that. I am a ham—so absolutely musical comedy or theater.
DL: My third question is, how much sleep do you get each night?
NG: Six to seven hours now, just because I’m old. Before that, four. Most of my life as a litigator, I never thought I needed sleep. You get into my age, you need sleep. And also you look like hell the next morning, so it’s either getting sleep or a facelift.
DL: And my last question is, any final words of wisdom, such as career advice or life advice, for my listeners?
NG: You have to do what you love. You have to do what you love. The law takes time and is so all-encompassing that you have to do what you love. And I have done what I love from beginning to now, and I wouldn’t have it any other way.
DL: Well, I have loved catching up with you, Judge, and having you share your thoughts and your story with my listeners. Thank you so much for joining me.
NG: You’re very welcome, David. Take care.
DL: Thanks so much to Judge Gertner for joining me. I look forward to reading her next book, Incomplete Sentences, when it comes out next year.
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