The Sentencing Matters Substack Interview: Assistant Professor of Law Raquel Wilson

If you were to make a list the people in the United States who know the most about federal sentencing law and policy, Raquel Wilson would be near the top of it. For eight years, Raquel was the Director of the Office of Education and Sentencing Practice at the U.S. Sentencing Commission. It was her job to know the Guidelines and to teach the Guidelines.

As Director, Raquel led a team of attorneys, former probation officers, and educators who ran sentencing seminars and workshops, put on national sentencing training conferences for judges, litigants, and probation officers, developed live and recorded online sentencing content viewed by thousands, and represented the Commission at various professional conferences and events on federal sentencing law and policy. In her time as Director, Raquel greatly expanded the Commission’s educational offerings beyond its traditional in-person training. They now include a range of materials on various platforms, including podcasts, one-page primers, newsletters, a sentencing glossary aimed at non-experts, and case law collections.

Raquel also had a significant under-the-radar influence on federal sentencing law and policy, both with the Commission itself and as she designed and delivered a sentencing curriculum to all new federal judges confirmed after 2015. She regularly advised the Commission on pending amendment proposals, and as part of the Federal Judicial Center’s orientation for new district court judges, Raquel delivered lectures and used scenarios and case studies as part of two and a half days of training for those new judges.

Raquel joined the Sentencing Commission in 2009 as Deputy General Counsel after serving more than ten years as an Assistant Federal Public Defender, first in the Southern District of Texas and later in the Western District of North Carolina. During her time as a defender, she represented hundreds of indigent persons accused of federal crimes, conducted numerous jury trials, and argued appeals before the U.S. Court of Appeals for the Fourth and Fifth Circuits.

Raquel left the Sentencing Commission staff in 2023 and is now an Assistant Professor of Law at the J. David Rosenberg College of Law at the University of Kentucky in Lexington. She teaches criminal law and procedure. I spoke with Raquel late last year. The interview was lightly edited for clarity and brevity.

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Jonathan: It’s so nice to talk with you, Raquel.

How do you like your new life as a teacher and academic? What do you love about it? What don't you love about it?

Raquel: I love teaching! I call myself the accidental law professor, because I had no idea that I would be doing this. As I’m sure you know, there's a specific trajectory for legal academic jobs, and I was not on that trajectory. Neither had I planned for this ever. This was all a surprise to me.

I especially like mentoring the students. I have mentored people throughout my career, including when I supervised people as Deputy General Counsel at the Sentencing Commission and when I ran the Commission’s education unit. But I had no vision for what it would look like to mentor 140 students a semester. I'm finding that it's really fun to get to know students from different backgrounds, many of whom will never practice criminal law. I didn't dream I'd be making all these little mini public defenders. But I think I'm doing that.

I also really like delving into the doctrine. I really enjoyed criminal law in law school – I enjoyed law school period. There are only so many people in the world who want to geek out on legal impossibility versus factual impossibility. I’m one of them. I have been focused on sentencing for the past 13 years, and it's been really nice to broaden out again and delve into more of criminal law.

I also love my colleagues. My colleagues here are great and very supportive, very encouraging. They read my work, comment on it, give me ideas for other scholarship. This is the best job ever.

Jonathan: That's fantastic. Is there anything that surprised you about the last year at Kentucky?

Raquel: I'm surprised at how much I enjoy being in the classroom. At the Sentencing Commission, I was responsible for training. But most trainings we did were one-offs. Maybe you’d spend a couple of days in a place. Mostly, you spent one day or several hours in a place. Any relationships you developed were very sporadic. It surprised me how much I enjoy having the time to build relationships with the students. Then once the students graduate, you have this small army, this cadre of people out there who remember the relationship and appreciate it. And even if they're not in touch with you year after year, you still know that you were able to have some sort of impact, that you had some meaning in their life.

Jonathan: Let's rewind just a little bit and go back to why you went to law school. How did you decide on that?

Raquel: Sure. When I was a kid, I wasn't one of those people who wore a suit every day and wanted to be a lawyer. I was really good at math and science in school, so at first, I wanted to be a marine biologist. Then, I wanted to be a chemist. Then I wanted to do neuroscience. I wanted to do all these different things. But I think what did it for me was mock trial in high school. First, I did just a touch of speech and debate. I realized with that that I enjoyed speaking in public and was not particularly afraid of it. I took a government class and then decided to participate in mock trial.

It was just a fantastic experience. Our team was very good. We made it to the finals in New York City, but lost to Packard. You know the feeling when you're in a flow – where you're working and working but it doesn't feel like work; you're just going and you're not even aware of time? You're in that flow.

I felt that way about courtrooms and about trials. I felt like I could do this all day. I could sit here and take notes on witnesses and get ready to cross-examine them. I could stand up and do an opening statement or take my notes for closing. You know all the things both in the courtroom, and then the things you do to prepare for trial, motions in limine . . . It's like I could do this all day.

And so I went to law school. I intended to be a trial attorney – actually intended to be a prosecutor.

Jonathan: So what happened? Why didn’t you become a prosecutor?

Raquel: I realized I wanted to be a public defender after my first several weeks of law school. I don't mean this to be ugly, but everybody cool was a defense attorney. I had Kathleen Sullivan for criminal law. I had Kim Taylor Thompson for trial advocacy. I just thought, “these people are smart.” And they seemed to be having fun and were focused.

This is going to sound hokey when I say it, but they were focused on the positive. No person is as bad as their worst act, right? We're all a combination of a lot of experiences and a lot of actions and emotions. And no person is as bad as their worst act. I felt like as a defense attorney, I could keep my focus on that, and as a prosecutor I would have to have the opposite focus of condemning people. I just didn't want to do that. I just didn't want that to be my whole consciousness.

Jonathan: After law school, you clerked, and then you didn't become a public defender or a prosecutor. How did you decide on that first job after school? And then how did you decide to later become a public defender?

Raquel: My answer will probably be disappointing, because the move right out of the clerkship was simply based on geography and my husband's career needs. I had had a two-year clerkship in Tallahassee. My husband had been working with the Florida government for two years. He needed to get a little more time in that job to set himself up for his next move. So, I took a job at Earthjustice Legal Defense Fund in Tallahassee. In a sense, it was a good fit, because in law school my other focus, other than criminal law, was environmental law. I was on the Environmental Law Journal. I was a founding member of the Environmental Justice Clinic we started in East Palo Alto. It could have been something that I stuck with for some more time, but I was ready to be in the courtroom and working with real people's problems. Not that the environment isn't real people's problems, but the work didn’t feel as direct.

Jonathan: Could you talk a little bit about your first few years as a public defender and how the experience shaped your view of the criminal justice system.

Raquel: I had a lot of fun as a public defender. It's a very stressful job, though. There's a steep learning curve; you're a baby lawyer, so there's a lot that you need to learn. As a federal public defender, you're doing a lot of your learning in public because you're doing it in the courtroom. You've got to stand up there and do that first bail hearing. Maybe you've watched a colleague do one. Maybe a colleague has sat with you when you did it for the first time. But ultimately, you have to get up and do it, and courtrooms are open to the public. The courtroom is full of people, and so you're learning in a very public space.

I had to just ignore that and do my job. I found that it was not that hard to leave clients with the belief that I was working for them and that I was fighting for them, because I was. The stakes are very high.

Part of the stress is that everybody lies to you. Let's be honest. Police officers and law enforcement officers lie. Defendants lie, witnesses lie, family members lie. Everybody's lying to you, and that's a lot to sort out. And as a defender, frankly, I'm not trying to get to the truth. That's not my job. My job is to mount a defense. But it's not easy when everybody's lying to you, or when lots of people are lying to you at different points. That part is stressful.

But I enjoyed the puzzle; working through things. I also really enjoyed getting the unprepared government witness, sinking my teeth into the witness on cross-examination. Overall, in those first few years, I felt like the things I had done – including mock trial in high school and the classes that I had taken in law school and the different things I participated in in law school – including, sadly, protests over the lack of diversity in the faculty at Stanford at the time – all of it prepared me well.

Jonathan: This interview is for a Substack that addresses sentencing law and policy, so let’s talk a little sentencing. Before you joined the public defender's office, did you have a view about federal sentencing or the federal Sentencing Guidelines and did those views change during your time as a federal public defender?

Raquel: I did have a view, because the judge I clerked for was brand new on the bench at the time and he had not studied criminal law since his time at Harvard in 1973. He had been a civil attorney during his career, and so he wanted our help with his criminal cases. And, of course, he knew I had an interest in it.

So we law clerks were very involved. Of course, everything was the judge's decision. But we read the pre-sentence reports. We looked over objections and did legal research on how he should rule. And we were very involved in sentencing.

I thought, as a law clerk that the Guidelines had a certain logic to them, and were somewhat straightforward, except for the guideline on illegal reentry. I remember having to figure out what an aggravated felony was, both for the guilty plea and for the pre-sentence report. That was very hard to decipher. But other than that, I thought that they were mostly straightforward. Now, of course, as a law clerk, you're getting the probation officer’s finished product. So it's going to seem straightforward.

When I became a public defender, I realized how much effort goes into working with the Guidelines; the arguments and discussions that are taking place before the pre-sentence report gets to the judge. I quickly understood that you could litigate sentencing issues. Over time, I better understood the depth of the issues and the need to focus on guideline determinations and litigating those issues.

Jonathan: It seems to me that federal public defenders are often more engaged with the Guidelines and their intricacies than Assistant U.S. Attorneys. Do you think that's right? And if so, why do you think that is.

Raquel: 100%! I have seen that from various perspectives. I have seen that as an AFPD. And I have seen that training AUSAs, which we didn't get to do as often as they needed.

As an AFPD, you need to use all the tools in the toolbox. Whenever your client is found guilty, you need to get that sentence down to the minimum that you can. You have to fight every point. So, you have to know those Guidelines in order to win; and you can win some of those arguments. I won lots of guideline arguments. I think, honestly, the AUSAs just don't have to work as hard because the probation officer has prepared the report and the attitude that I observed was, it's in the report, so there you have it. They just didn't feel like they had to do any more work. Sometimes they did if the defense objected, then they might engage. But honestly, I didn't see a whole lot of engagement, and they often would not do a rigorous analysis in my experience.

Jonathan: With all your experience, you're someone who knows the Guidelines better than almost anybody in the country. What's your overall assessment of the federal sentencing guidelines? And if you could change a couple of things about the Guidelines to improve them, what would they be.

Raquel: So that question is very complicated for me, and I will try to express succinctly why.

Guidelines as a concept are a good way to reduce the impact of bias. This is something that has been studied and discussed in social science, outside of sentencing. Using guidelines is a good way to combat bias; personal bias, racial bias, whatever the case may be. Having written rules, expectations, and procedures that people have to follow leaves less room for bias than relying on wide open personal judgment. So as a concept, I'm supportive of the notion of guidelines.

I think that the federal sentencing guidelines are oftentimes just too severe. The sentences are just too long. But I don't want to lay blame on the Sentencing Commission specifically. I don't believe you can lay blame for the plight of the Black man in America on the U.S. Sentencing Commission. I think racism in America and in the criminal justice system is far more complicated and widespread than the federal sentencing guidelines.

That said, mandatory minimums are a blunt instrument and intended for people that by and large the U.S. government does not prosecute. We're not catching kingpins, like El Chapo and his son and their associates. That case is the one in 50,000. Mandatory minimums were intended for people like that or their close associates. Instead, the government catches the low hanging fruit pretty much whenever they want to.

Start a sting operation, end it when you want to. It used to be, you end it when you get to 28 grams of crack cocaine. Now maybe you end it when you get to 280 grams of crack cocaine. But the government is in the driver's seat.

I think the way mandatory minimums operate is cruel and generally ineffective in terms of bringing down drug usage, drug trafficking, and so forth. I'm not going to say that the Guidelines should be unmoored from mandatory minimums. But I wonder if the Guidelines couldn't give some sort of advice about what the sentence would be without them.

In terms of other things to change, criminal history is complicated, and people who apply the rules, not just probation officers but defense attorneys and prosecutors too, they make mistakes. I've seen those mistakes. I also wish that criminal history didn't have such a severe impact. I know the studies about how reliable a measure it is in terms of recidivism. I’m just not sure it needs to have such an impact on the sentences.

You could have the points readily available for the judge and then have perhaps some broader categories. It would be a pretty easy way to reduce penalties, because they're just too long, too much time, and yet still acknowledge that criminal history score has a predictive value. There are a lot of factors that play into recidivism that we don't understand and don't have control over.

Jonathan: Is there anything else you would change about the Guidelines?

Raquel: I wish the Guidelines could be written as graphics. While I was running training at the Commission, I thought the Guidelines could be improved with flow charts and decision trees, annotated to better guide people through how to apply them.

Many of the people who are applying the Guidelines are non-lawyers. I wish there were some sort of equalizer where any person – that could be family members or members of the public – could open up the book and understand what it was saying. I don't think you do that in words.

Jonathan: Do you have any thoughts about the way the Sentencing Commission goes about its business? Is there anything you would change about how it operates?

Raquel: I think the Commission staff is its best kept secret. I didn't have any idea before going there the level and breadth of expertise of the people at the Commission. I had no idea.

I always wished that there was more information flow back and forth between the public, social scientists, others, and the Commission staff. I understand that the Commission is an administrative rulemaking body. But it also serves an important role in educating. And I don't just mean training on Guidelines. Just educating – and also receiving information – on criminal justice policies. The Commission is supposed to be a clearinghouse for sentencing data and information. Yes, there's annual report and many, many very helpful reports.

But if I could change one thing, I would take the Commission on a road show. The commissioners and staff could talk to academics, hear from academics, talk to community members, hear from community members. I attended my fair share of public meetings, even in different parts of the country. But there are a lot of people to hear from on criminal justice, because criminal justice is proximate to a lot of people, a lot of different kinds of people. I know that anecdotes don't make policy. And they shouldn't.

But I did wonder sometimes whether we could just hear more from a broader swath of people who are affected by our criminal justice practices. There's no reason, for example, why a member of the community couldn't be appointed to the Sentencing Commission. I think it would lead to a very meaningful exchange.

Jonathan: Can we talk a little bit about some of your academic work. You've just published an article on the First Step Act. In the article, you seem quite skeptical about the value of in-prison programming. You use some provocative language in the article where you say that in-prison programming – and I'm quoting here – “may provide cover for our collective dysfunction, softening the reality that we are simply warehousing people, and making the prospect of sentencing them to years or decades in prison more palatable.”

Could you talk a little bit about your feelings behind those words, what makes you skeptical of in-prison programming, and how such programming impacts sentencing decisions?

Raquel: I know that many judges take in-prison programming very seriously. These judges regularly seek information on what programs are available; they research the programs and make recommendations to the Bureau of Prisons on where to house people and what programs to make available to them.

Some of the programming has been shown to reduce the risk of recidivism, most notably the BOP’s residential drug abuse program. Some of the programming has been shown to be effective in managing the population.

Now, to me, those are two very different things. Reducing the risk of recidivism is clearly aimed at public safety, which I think should be a foundational principle for sentencing. And not just for violent crimes; we don't want fraudsters to repeat their conduct either.

But when it comes to managing the prison population, I understand the value of that, it's necessary. But query whether the population should be in prison to be managed in the first place, when there are other ways to address the crimes.

Also, when sentences are very long, people in prison run out of programs to take. I saw this touring various BOP facilities. There were men who had been locked up in federal prison for decades. And they had taken every program available, some multiple times. They posed little to no risk if released. And they were often model citizens within the prison. Prison guards and administrators don't know what else to do for these men. They're out of options. The men are not a problem because they're older. They've been in prison for decades.

I would see the heartbreak on the faces of the prison staff and administrators and the heartbreak and the dejection on the faces of the men who had been locked up for decades. They would have no reason to believe that they would be released before they die. And so, to the extent that we're offering prison programs to manage this population, I'm questioning why the population is incarcerated at all.

Moreover, prison work programs, which are very popular with judges, I'm not sure those programs have any science behind them in terms of reducing recidivism or helping people get gainful employment. Given the realities out there of not just discrimination against people with criminal history, but the realities of the workplace and AI and robots and all of the automation, finding and keeping those jobs is very challenging as the nature of work changes.

And frankly, it's very disappointing to me how much stock we put into prison programs when you compare them to the value of education, which is one of those programs that has indeed been proven to reduce recidivism. With every college credit earned, recidivism is reduced. And so, while I can appreciate that a person might get a forklift operator job when they finish prison, I wonder why we aim so low. I think that we've aimed low for certain segments of the population for their whole lives, and frankly for generations. Prison can be a continuation of that injustice.

Jonathan: Do you think your scholarship is going to continue focused on sentencing and corrections?

Raquel: It will broaden out. I'm still interested in sentencing and corrections, because ultimately what we do to people who have transgressed our rules is a very good way to judge our society; how we treat the least of these. So, I will continue to be interested in it.

But I definitely have broader interests that I'll have time to explore. For example, I spent three weeks in Grenada this summer looking at what's behind their “mass incarceration.” Grenada has one of the highest per capita incarceration rates in the world, which is shocking for such a small country that is actually very safe. As a tourist you can go and stay in the all-inclusive resorts certainly. But it's a safe country. You can walk around on your own. You can hire your own taxi driver and go see waterfalls and beaches and all the things without being concerned about your safety.

So it was shocking to me to see that they had such high numbers. It's also a Black country. We talk about mass incarceration here as an issue of social justice and racial justice. And it is, don't get me wrong. But what explains very high rates of incarceration in a Black country that's a stable democracy?

And so my recent trip there was fascinating. I'm still processing the information and will certainly need to go back to continue my research. The people there were incredibly gracious, spending time with me and allowing me into various facilities.

Unpacking what is happening there and in other Caribbean Islands is very interesting to me as a different lens to see mass incarceration. It can inform how we think about it and talk about it in a multicultural society. Ultimately, locking people up might just be part of the human condition. It might just be what we do as people . . . except the people in Finland. Somehow, they've escaped this.

Jonathan: Do you have any plans yet to release any of your findings?

Raquel: That is a very tough question for an academic. I think this work will lead to a series of papers, because there is a lot there.

Jonathan: There are many of us who will be looking out for these papers and your other scholarship. Thank you so much for taking the time to talk. Have a great rest of the semester.

Raquel: I appreciate the time and the interest.