The Sentencing Matters Substack Interview: Retired U.S. District Court Judge Mark W. Bennett

Mark Bennett has been living a lawyer’s best life for 50 years. He started his own law firm straight out of law school in 1975. He argued a case before the U.S. Supreme Court before he was 30. He represented hundreds of clients in criminal and civil rights cases as a private lawyer. He became General Counsel of the Iowa Civil Liberties Union at age 25, a job he dreamed about and that first drove him to law school and to move from St. Paul to Des Moines. He was appointed to the federal bench by President Bill Clinton in his 40s and was confirmed by the Senate unanimously. He has taught classes throughout his career at universities and community colleges and has led hundreds of continuing legal education courses. He has published dozens of law review articles, and his scholarship on sentencing, implicit bias, and the psychology of anchoring has been cited more than a thousand times. He is co-author of an employment law treatise and now works as an arbitrator and mediator. His career has been remarkable and a model to be admired.

But for this Substack, Judge Bennett is first and foremost one of the leading critics of federal sentencing law and policy and has been for decades. While on the bench, he sentenced over 4,000 men and women. He knows a thing or two about sentencing. Earlier this year, Bennett published an article, “My Half Century Traversing the Arc of Federal Sentencing.” And in it, he sums up his views about federal sentencing this way: “federal sentencing over the past 50 years has been a tragic mess.”

Judge Bennett has not been shy about criticizing the U.S. Sentencing Commission, congressional sentencing enactments, and the Department of Justice. But he is not just a critic. Judge Bennett cares deeply about the people impacted by crime and sentencing, and as you’ll see in this interview, he has acted on that commitment not only in his judging but in giving of himself to those who get caught in the web of the criminal justice system.

Professor Doug Berman and I had the great honor and pleasure of speaking with Judge Bennett this spring. The interview was lightly edited for clarity and brevity.

-Jonathan

- - -

Jonathan: Thank you so much for sitting down with Doug and me. I’d love to start by asking you to talk a little about where you grew up, what your childhood was like, why you decided to go to law school. We'll get to sentencing and why you hate the Guidelines in a moment.

Judge Bennett: Ha! Ha! Ha!

Well, my childhood actually had a huge impact on my philosophy as a judge, and on sentencing, too. I grew up through 6th grade in St. Paul, Minnesota. I had a pretty normal childhood. We lived in an upper middle-class neighborhood, three houses from the elementary school I attended.

I had an experience in first grade that influenced my whole life and especially my career. My best friend lived across the street from me, and he wound up in special education. He was very slow, and in my first-grade class, the teacher was always picking on him. One day, my teacher said to another student, “if you don't work harder, you're going to be just like Bobby,” who was my friend, and I stood up out of my seat. I pointed my finger at the teacher, and I said, “Mrs. Churchill, don't you ever say that about my friend?” She came over and grabbed me by the ear and marched me up to the principal's office, where I got a huge chewing out from the principal.

I was sobbing. The principal called my Dad to take me home, because I was so upset. We're walking home, and my Dad had his arm around me, and he said, “you know I'm really proud of you, because in life sometimes you never get a second chance to stand up for what you see to be an injustice.” That left a huge impression on me. But I said to my Dad, “why didn't you stand up for me in front of the principal?” And he said, “oh, because you need to learn to stand up for yourself.” All these years later, it still has an impact.

My mother was also very ill when I was young, and she passed away when I was 13. Before she died, my parents hired an African American nanny to take care of me and my two siblings. She would come several days a week because my mother really couldn't do a lot of housework. I became very, very close to her. I considered her like my second mother. When I would come home from school, I would sit on her lap, and I would ask her about her childhood growing up in the South and then moving to the Twin Cities. She was always matter of fact about it, and she was never bitter. I was shocked by the discrimination she encountered in her life, and it left a huge impression on me. I carry these experiences with me to this day.

Doug: Did you have any lawyers in your life?

Judge Bennett: No, never, none.

Doug: How did law school become the path that would allow you to stand up for yourself and others?

Judge Bennett: Sort of indirectly. My parents belonged to the ACLU, but they were just dues paying members. They never did anything other than pay dues. But we got a newsletter, and I would read it as a young child. I thought, “wow, to be able to be a voice for people who needed a voice.” Well, that's what lawyers do. It wasn’t until I was in college that I actually met a lawyer. But that ACLU newsletter had a huge impact on me.

Why Drake law school? A couple of reasons. I was an avid downhill skier, and I was accepted at Denver. But I knew if I went there, I would probably flunk out. But the bigger reason why I went to Drake is I wanted to become the first ACLU lawyer in Iowa. There wasn’t a single one back then. It was also close to home, and one of my best friends from college went there. I went down a couple of times to visit, and I really liked Des Moines. It kind of reminded me of St. Paul when I was growing up.

Drake was also one of the first law schools in the country to have a real active clinic. I got to actually try a case in federal court with a lawyer who then became a partner of mine after I graduated. As a student, I also represented a streaker, if you're old enough to remember what that means. I got the Des Moines city ordinance on public nudity declared unconstitutional as a second-year law student.

We're actually having our 50th reunion tomorrow. I'm so excited. Law school was a great experience. I'm very fond of Drake, and I have a huge debt of gratitude for the education I received there. I've tried to pay back that debt by teaching on and off as an adjunct for many, many years. Before I became a judge, I spent over 10 years teaching trial advocacy. I've taught an advanced employment discrimination class, where I’d drive down from Sioux City on Sunday to teach the class Sunday night. Then, I’d drive over to Nebraska and teach the same class at the University of Nebraska Law School. And then after that class, I’d drive back to Sioux City and start a jury trial on Tuesday. So that was kind of my routine for several semesters.

Doug: Early in your career, you argued a case before the U.S. Supreme Court. What was the backstory on that?

Judge Bennett: It's kind of funny. A lawyer in town who didn't know very much about employment discrimination asked me for some help on a case. He didn't follow my advice, and the case was not properly filed with the Iowa Civil Rights Commission and the EEOC. I filed a lawsuit in federal court to try to fix it, got hit with a motion to dismiss, and lost. I appealed the case, lost in the 8th Circuit, and then filed a petition for rehearing. Incredibly, the petition was granted, and I ended up winning the case. The other side then filed a cert. petition, which got granted.

In preparing for the argument, I found something like 42 decisions on the precise issue before the Court. I studied them, and I knew them all cold. But when I went to argue the case, I wasn't smart enough to know that I should have hired an experienced appellate advocate to argue it. I was only 29, but I had already argued several cases in the 8th Circuit and several cases in the Iowa Supreme Court and done ok. I thought I could do it.

Early on in the argument, I came to the realization that I was a bit over my head, despite the fact that I knew the cases cold. The justices asked higher level policy questions that, of course, I hadn't given much thought to. But I was at least smart enough to cede 15 minutes of my argument time to the Department of Justice. They had a lawyer who came in and cleaned up my mess. Of course, my Dad flew out for the argument; my wife too. They all thought I did a good job. I did a terrible job. It may go down as one of the 10 worst oral arguments in Supreme Court history.

But later, I had three more cert. petitions that I filed that were granted before I was 32. They were always companion cases, so I was more than willing to cede the argument to better lawyers, better appellate lawyers. It was a great experience and very humbling. I think we learn more from experiences where we don't do as well as we had hoped we would, as long as we do a postmortem. I still do that. I do a lot of mediations now, and I always do a postmortem. What did I do right? What could I have done better? I have a personal mantra — when I wake up in the morning, I ask myself what can I do better today that I haven't done before. I'm a lifelong learner. I've always tried to get better at what I do, because I'm mistake prone, and I recognize it.

Jonathan: Judge, I found the Supreme Court argument on the Internet and listened to it.

Judge Bennett: Oh, God!

Jonathan: I wouldn't have ever characterized it the way you did. I did note, though, that you responded to a question from Justice Stevens this way, “I don't know the answer to that.” I loved it.

Judge Bennett: Yes. I've always told students that if you don't know, just admit it. We have what's called Supreme Court Day at Drake, where students get to argue a mock case. I often ask questions to which they have no idea what the answer is. Sometimes they try and fake it, and then they're really in trouble. So, I always tell them, I had to say it to the Supreme Court: “I don't know.” I think justices and judges will respect you when you say that, because when you try and bluff them, they're just better prepared than you are. It's nothing but trouble down that road.

Jonathan: Judge, as you know this interview is for a Substack that focuses mostly on sentencing. You've been an outspoken critic of federal sentencing law and policy for a long time. Can you summarize your views on this and why you feel as you do.

Judge Bennett: Yes, thank you for that question. I had done just a few sentencings as a lawyer. We had hired a former AUSA to join our firm; he handled most of the sentencings. When I became a judge, though, I started doing a deep dive into sentencing. I remember that in what we call Baby Judges School, we had some folks from the federal Sentencing Commission that were great trainers who taught us all about the Guidelines. They were fabulous, just fabulous, but they were, what I recognized later to be, “Kool-Aid drinkers” in the sense that they absolutely believed at their core that the Guidelines were empirically based.

I've always questioned things as a federal judge. My favorite t-shirt I wore at home said, “Question Authority.” One time, my daughter, who was probably about eight years old at the time, reminded me that “Daddy, you are the authority. Why do you wear that t-shirt?” I explained my philosophy about questioning everything.

As a judge, I started doing a personal deep dive into the work of the Sentencing Commission. I came to the belief that the Guidelines were not empirically based in the sense that the Commission had indeed looked at 10,000 pre-sentence reports in developing the Guidelines, but had excluded 5,000 of those where the defendant had been sentenced to probation. The Commission didn't use those cases in the calculations to come up with the Guidelines. And they've never, to this day, as far as I know, publicly explained how they came up with the Guidelines.

In Baby Judges School, you're taught that the Guidelines are empirically based. They repeat that phrase all the time. My own view, whether right or wrong, is that it’s a fraud; that the Guidelines are not empirically based, or if they are, it's a secret, and we don't know how. That was the impetus for the start of my criticism of the Guidelines.

Then, I sentenced over 4,000 offenders as a federal judge. You might think that the Northern District of Iowa is a sleepy little district. We actually have a very heavy criminal docket. If you took the criminal caseload of a typical judge from the District of Columbia, the Southern District of New York, the Northern District of Illinois, the District of Minnesota, and the Northern District of California, and you added up their criminal sentencings, I had more sentencings than they all did together in a year. I spent an enormous amount of time reading pre-sentence reports and doing sentencings. We had excellent probation officers, and I did sentencings in a number of other districts as a visiting judge too.

Doug: If the Commission had either explained the empirical basis for the Guidelines, or, if they did, past or present, a more transparent and satisfying empirical analysis, do you think that would be sufficient? Does a national empirical basis make sense for Iowa, or should it be an Iowa-based empirical analysis? How do you sort through making good guidelines, given all the experiences you've had?

Judge Bennett: I'm much less interested in what other judges do. As I recall, when I raised my hand and I was sworn in, there were no probation officers raising their hand; there were no other judges raising their hand. It's a very solitary decision-making process being a judge.

Before I go on, I want to thank you, Professor Berman, for your blog, which I spent more time on than any other part of the Internet. It is great. I got a lot of my ideas from it. I very seldom have an original idea. But I'm really good at spotting an idea that resonates with me and then trying to expand on it. And your blog was, honest to God, the most influential thing for me. In my 24 years as a United States district court judge, your blog had more influence on me than anything else, and for the better.

Back to your question, I think I might have been a little bit more guideline-centric if that empirical information had been disclosed. Of course, I would have made my own independent judgment, too. I was never willing to defer to the Commission, particularly after Booker. I gave it weight, but certainly not as much weight as most other judges did, and certainly not as much weight as my beloved colleague, Linda Reade.

I want to tell you a few things about that, because I think it's very interesting. Judge Reade and I have very different sentencing philosophies. I first met her before she was a lawyer, when she worked in the Dean's office at the law school. I got to know her, and I encouraged her to go to law school. And she did, and then she went into private practice for a little bit. She became an excellent state court judge, and I was absolutely thrilled when she became my colleague.

Lawyers thought we hated each other, because they didn't know the backstory about our friendship. In all the years that Judge Reade and I were colleagues, we never had a single disagreement. Never. I consider her a great friend. I have great respect for the independence of the federal judiciary. Defense lawyers would often cry and moan to me about her, and I would say, “hey, she's got as much right to have her sentencing philosophy as I do. If you've got a problem, go to her.” I'm absolutely sure that most of the AUSAs in the Northern District were complaining to her about me. I don't know how she responded. But I'm guessing, she responded, like I did. She and I talked about everything. But we've never talked about our sentencing philosophy. Ever.

Jonathan: Do you think it's a good idea to have the Commission try to lessen the differences among judges with different philosophies? Do you think that's a legitimate goal of sentencing reform?

Judge Bennett: I think it could be. As you both well know better than I do, the Sentencing Commission was created because of political concerns about unwarranted sentencing disparity. I get that. There was too much unwarranted sentencing disparity. But what we got was unwarranted uniformity. So, pick the devil you want. I thought unwarranted uniformity was worse than unwarranted disparity, but that's just a personal view I had. I recognize that other people saw it very differently.

At bottom, I like the Guidelines’ structure the way it is now. But the problem is that new judges never sentenced like I did prior to the Guidelines. So, the judges who are now confirmed grew up with the Guidelines. I wrote a law review article published in one of the Northwestern journals on criminal law about the anchoring effect of the Guidelines. I've done over 50 different anchoring studies. Anchoring is incredibly powerful, and judges are anchored by the Guidelines. It is one of the reasons most judges are very guideline-centric. There are other reasons, too. If you give a guideline sentence, you're not going to get reversed. How many guideline sentences have been reversed on substantive grounds? I only recall one or two. It also gives you some personal comfort to know that you're sentencing like other judges who are guideline-centric. Some judges find solace in that. That's okay. I don't. I don't care what other judges do. My goal is to do the best job I can to determine a sentence looking at the section 3553(a) factors.

Doug: You’ve written a lot criticizing the drug guideline, criticizing the fraud guideline. Do you think to some degree, the guidelines get a bad name because of certain bad guidelines? If the Commission could more proactively address the worst aspects of the Guidelines, do you think the entire system would get more respect from a range of judges? I look at the data on firearm sentencings, for example, and it seems like there is a pretty high percentage of sentences that are within the guideline range.

Judge Bennett: I like the structure post-Booker and post-Gall. Before Booker, I would set Fridays for resentencing, because I got reversed so often. It didn't bother me. I would usually give the same sentence on resentencing with a different rationale, and sometimes I would get reversed again, and sometimes I wouldn't. Once, I got reversed five times in two different cases. Both cases went to the Supreme Court, and the Court adopted my view. After that, the Eighth circuit left me alone. Now, I use Fridays for other things. I rarely have a resentencing.

Now that we have more discretion, I think judges need to be taught about anchoring and implicit bias. I was the first judge in the country to come up with an implicit bias jury instruction, and I've taught more than 4,000 lawyers about it. I want them to know how powerful guidelines are. Anchoring is an unbelievably powerful psychological phenomenon. It's very hard to resist. I've never, at all the judges’ conferences I went to, ever heard a cognitive psychologist talk about the powerful anchoring effect that the Guidelines have.

Every guideline that uses quantity is, in my view, irrational. Drugs, fraud, guns, child pornography . . . One of my very first sentencings as a judge addressed whether there were 100 marijuana plants or not. I had two expert witnesses testify. They were botanists from the University of Illinois in the same department, and one testified that the 104 plants that were seized were really 98, and the other botanist testified they were really 102. I went with 102, and the defendant got hammered, because it was above the 100 plants [threshold]. I had a gun case with a person who lawfully was a gun dealer, but he gave up his license. He still had like a hundred guns in his house, or in his warehouse. Maybe he was a felon or something, I don’t remember. He came before me for sentencing. You looked at all these guns, and his guideline range was jacked up really high. But wait a minute. He lawfully had the guns; at one point he was a gun salesperson. He never used any of the guns for any illegal purpose. I did a substantial variance.

Then there’s child pornography and the number of images. What's magical about the number of images? And you have one image more than that, and your guideline range gets jacked up. With the fraud guidelines, I have criticisms in both directions. I think they were too low at the bottom and way too high at the top. I once sentenced a mail delivery person from a small town. She would rifle through the mail and see envelopes that she thought might have a check in them, and she would take them. The [loss] amount was very low, but I had victims come in and testify . . . “I sent a check to my son on his high school graduation or college graduation, and he never got the check.” There were a series of victims who testified like that. The guidelines were incredibly low. I hammered her. She got an abuse of trust enhancement. But that wasn't enough to cover what I viewed as the seriousness of the offense.

And with violent criminals. Oh, my God! The Northern District of Iowa . . . they were soft on violent criminals. Why, I never could figure out. I would say 95% of the time, I gave a harsher sentence than what the government recommended in violent crime cases. So, it wasn't just a one-way Liberal Mark. As a matter of fact, for some defense lawyers, I'm sure my nickname was Maximum Mark.

Jonathan: Related to these critiques, you said yourself in an article that no other area of law has engendered more criticism from the public, scholars, and criminal justice professionals, than federal sentencing. Yet it strikes me that the basic structure of the sentencing guidelines and mandatory minimums have persisted for almost 40 years. Why do you think that is?

Judge Bennett: You name me a congressperson that has run on a platform of being softer on federal crime. Now, some have individual criticisms, but you can’t name a politician who said the Guidelines are too harsh, or that they weren't empirically based, or that they're unfair. The 100-to-1 crack/powder ratio was unfair. Yeah, there were a couple congresspeople who said it, and credit to the Sentencing Commission on that issue. They were really good on it. It was Congress who nixed them early on, when they made a recommendation to reduce the disparity. But congresspeople don't have the will to tell the truth about federal sentencing, in my view. So politically, it's just not going to happen now. On the other hand, Senator Grassley, our Senator, pushed some important prison reforms, like the First Step Act. So, credit him too.

Doug: In a recent article, you wrote about visiting prisons and seeing both folks you've sentenced and others. If you could decree that every federal judge needs to make those visits, would you?

Judge Bennett: It's fair to say I've been a super vocal critic of the Sentencing Guidelines. But what I haven't done is try to proselytize to any other judges, including friends of mine, to adopt any of my sentencing views. I have great respect for the independence of the federal judiciary, and some of my closest friends on the federal bench with whom I would talk sentencing thought I was nuts. That's okay. I thought they were nuts, but I had respect for them.

So, I'm not going to tell other judges they should visit inmates. What I am going to say is it was one of the most fulfilling things I did as a federal judge, for so many reasons. I visited over 400 inmates. It was very powerful for a couple of reasons. First, too often, I was the only visitor the inmate ever had. They would tell me that the fact that I would come and visit them and take time out of my schedule, they just couldn't believe it. It was like, “what are you doing here?” The very first time I went to visit inmates I had sentenced, I couldn't get them to talk; and I can usually get people to talk. So, one guy finally raises his hand, and he says, “well, judge, we're worried that you're here to raise our sentences.” I explained to him, no, I can't raise or lower your sentence, at least not today.

I just found interacting with inmates really helpful to me. I would visit the in-prison programs with them. I would go to the residential drug abuse program. I would sit through classes with them. I would eat with them. I would go to their work placements with them. I wanted to know what it was like, and then I would meet with them in a group, which was great, and meet with anyone who wanted to meet with me one-on-one.

Of course, it was the one-on-ones that I really found to be the most meaningful. A good example was with a guy I had sentenced. He was Caucasian, came from a very wealthy family, lived in an $800,000 house right outside Sioux City, and he was a big-time drug dealer. He had all the advantages in life that most of the defendants I sentenced did not have. I gave him an above-guideline upward variance.

When I got the list of who I was going to be visiting that day, I saw his name, and I knew he wasn't going to be happy with me. And he wasn't. But he asked to meet with me privately, and we did. He was a big, strapping, good looking guy. We're sitting in a room by ourselves – no staff – and he said, “why did you sentence me above the top end of the guidelines?” And I said, “do you want to know the legal reason or kind of the colloquial reason.” He asked for the colloquial reason. “I thought you were an asshole in many respects. You didn't do anything for the community other than infuse the community with a ton of drugs.” There was nothing in his pre-sentence report that indicated he was remorseful; that he had done anything to help anybody in his life. I told him, “you were a selfish, self-centered, self-indulgent asshole drug dealer, and that's why I gave you the sentence.” And he looked at me and he said, “you're right. I was.” He paused, and he said, “but I'm not any longer.” I said, “well, tell me about that.” I probably spent close to an hour with him, learning about what he had learned about himself and what he had been doing with his time. If I could have waved a magic wand, I would have released him that moment. But I'm glad I didn't have the power to do that. One of the things I learned from these visits is that it would usually take into the second or third year before inmates had any self-awareness about the harm that they committed. Some never did, but if they did, they wouldn't get it in the first year. It would take a couple of years.

Hearing that repeatedly from different inmates I had sentenced in different prisons all over the country had an impact on me. It made me believe that maybe shorter sentences might actually benefit society more than incredibly long sentences. Of course we had mandatory minimums. There wasn't anything I could do about it. I still found great value in visiting inmates. I would get letters from them. I would try and help them in any way I could.

I would also visit prisoners in halfway houses. The biggest problem I found there was that they didn't have driver's licenses. It was hard to find a job without the license. They would have to walk in the middle of winter when it was below zero. Some of them had overdue fines that were getting in the way. I'd work with their families to try and get the fines paid. I had lunch at the halfway house once a month to meet with the inmates and tell them what my expectations were for them on supervised release. I found those interactions very, very helpful.

Jonathan: Judge – thank you so much for talking with us. Your life’s work has been remarkable. We really appreciate you sharing it with us.

Judge Bennett: I want to say how deeply appreciative I am of the two of you and the work that you've done. I have tremendous respect for both of you. Jonathan – I think it's fair to say, we didn't often agree. But I think when we disagreed, we weren't disagreeable about it. I know you weren’t. I probably was, and I apologize for that. The older I've gotten I've learned to be less disagreeable. I think the fact that we have these debates, and that people have different views, is a very, very healthy thing.

It was a great honor to be a federal district court judge. There were several reasons why I decided to retire. One, there was a certain sameness to the job. I didn't find it as challenging as I did early on. But the big reason was I just got tired of populating the Bureau of Prisons. It's a job that had to be done, and I think I did it for the most part to the best of my ability. I just didn't want to do it anymore. And I thought, too, I had maybe two more careers left in me.

I hope I gave you a little bit more insight why this judge, in this little old Northern District of Iowa, in Sioux City, Iowa, had these views that were different than the vast majority of my colleagues.

Doug: Thank you, Judge. We really appreciate you doing this.

Judge Bennett: Thank you guys so much. What an awesome pleasure!