On Being a Great Prosecutor

And a Holiday Wish for You and Yours

Prelude

Six months ago, Doug, Steve, and I started this Substack as a new space for commentary about sentencing matters. At its core, sentencing is our government, acting on our behalf, inflicting pain and obligation – sometimes lots of it – on our fellow citizens as an accounting for those citizens’ misdeeds. Sometimes it’s just for retribution. Most of the time, it’s for other purposes too.

While sentencing is a common phenomenon – it happens thousands of times every week, in every state and every county across our great country – it should never be taken lightly. It deserves scrutiny. This is a critical element of the never-ending fight for freedom and liberty that is part of the foundation of this country – maybe the most admirable part – and one we need to have front of mind regularly, and especially now. This is what we’re trying to do here.

We decided to start the project in July in order to see through, and let pass, the end of the October 2023 U.S. Supreme Court term. And we thought we would start with an essay on how Judge Juan Merchan of the New York State Supreme Court should sentence Donald Trump for his convictions for accounting irregularities. You remember – the sentencing was scheduled for July 11^th. Of course, Chief Justice Roberts’ opinion granting presidents immunity for their official acts, handed down on the last day of the U.S. Supreme Court’s term, changed lots of plans, including ours. If you’re curious what I was thinking back then, here’s an excerpt from that first essay, which we never published –

So, what is Judge Merchan to do? After methodically reviewing and reasoning through each of the issues raised by the parties and by any presentence report, after giving Trump an opportunity to address the court, and after making clear that Trump, like every other citizen, must be held accountable for his various misbehaviors and criminal conduct, Merchan must find a way both to hold Trump accountable and simultaneously have as minimal an effect as possible on the upcoming election and on the country more generally . . .

Merchan should place Trump on unsupervised probation for a year – with the standard conditions imposed on all those placed on probation – but then defer a decision on any additional probation conditions until after the election. Judge Merchan should assure Trump – and all of us – that if Trump complies with the standard conditions, he will not impose a custodial sentence . . .

And when the appointed time comes after the election to impose those additional conditions, Judge Merchan should order Trump to meet him on Fifth Avenue, the same Fifth Avenue at which Trump boldly asserted he could shoot someone and not lose the allegiance of his voters. It would be just the two of them on an empty street, with two chalkboards, the kind you might find in an elementary school classroom. Judge Merchan would begin by walking up to the first of the chalkboards. Standing in front of it, he would write on the board 10 times, “As a New York judge, I shouldn’t have donated to a political campaign.” Then after he is done, he would hand Trump the chalk and order him to the other chalkboard to write 10 times, “Like all Americans, I must follow the law too.”

In the 26 essays we have published over our first six months, we have explored why reviewing especially long sentences might be a good idea now and then, how decisions on priorities, guideline amendments, and retroactivity get made at the U.S. Sentencing Commission, why diversity of thought in making sentencing policy is a good idea, and so much more. We have channeled our inner Taylor Swift, learned sentencing lessons from the English Premier League, commiserated with former Congressman George Santos, and written a new federal drug sentencing guideline.

We’ve thought about charging policies, originalism and sentencing, clemency and pardons for turkeys and others, how being young should or shouldn’t affect sentencing decisions, and what the election of Donald Trump as President means for federal sentencing and the U.S. Sentencing Commission. We’ve interviewed some interesting people, reviewed a couple of sentencing books, and marked the 40^th anniversary of the Sentencing Reform Act. We’ve tried to be true to our mission to scrutinize sentencing, regularly.

We genuinely appreciate you reading our essays and being part of this project. Through our writing, we are trying to uncover an insight or two and share that thinking in a mildly interesting way. We hope you will continue to join us as we grapple with the important issues of crime and punishment, remorse and forgiveness, policymaking and politics, law and judging, and freedom and justice in the year to come. We’d love to hear from you now and then. And we’d love to bring in new voices to this conversation, including yours, including those serving – or who have served – time in prison, victims of crime, prosecutors, defense lawyers, probation officers, judges, other academics, and just other everyday citizens. We’ve tried to create an aesthetic on this Substack that is serious, at times just a little bit snarky, but always gracious. If you’re at all inclined to contribute something, let us know.

We’re going to give everyone a week or so off from new content. We have one more essay for the year for you below (consider this a special holiday double issue). But then enough sentencing until the new year. We’ll be back with our usual Monday morning postings in January.

And as you sit down with your families for the holidays, remember, if only for a short time, that there are hundreds of thousands of men and women who, at that very moment, are mourning family members lost to crime, hundreds of thousands of men and women serving the holidays in prisons and jails, and hundreds of thousands of men and women spending the holidays keeping us safe. God bless them all. And our best to all of you and your loved ones for a wonderful holiday season and a joyous 2025.

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On Being a Great Prosecutor

A few weeks ago, I was strolling through Cambridge Common, and then later Harvard Yard, for what would be the last time for the fall semester. For 12 weeks, on Mondays, I would fly up to Boston from Washington and then make my way to Cambridge for a couple of days to teach and learn at Harvard Law School. A semester that began with warm and long September days and shirtless runs along the Charles River was now a very cold, dark December late afternoon. The leaves had fallen from the trees in the Common. The hummingbirds and the robins were gone. And there was a hint of snow and patches of ice on the ground.

Diueine Monteiro

Students were back from Thanksgiving. They hustled through the Yard just a little faster than before. The change of season brought a penetrating wind, along with the cold, and it was also time to start preparing for exams.

It is a great privilege to be able to spend time on the Harvard campus. There are so many interesting people who come by for lunch talks or panel discussions or to judge a moot court: presidential candidates, authors, judges, other public officials of one kind or another. But it is a special privilege to spend time with young, bright minds, the lawyers of tomorrow. I have plenty of elderly colleagues who complain about Millennials and Gen Zers. You may be one of them. I have no complaints, though. The students in my classes are, almost to a person, thoughtful and diligent, kind to one another and passionate about justice, and just a pleasure to be around. Maybe it’s just in front of me and because I hold their grade in my hands. I’d rather think not.

We gathered as a class one last time on that final Tuesday afternoon of the semester in Room 100 of Pound Hall. This year, I taught a Government Lawyer class that included 30 second- and third-year law students and one fellow from the Kennedy School of Government. The class is part of a clinical program, where students work 16 hours or so a week in various sections of the U.S. Attorney’s Office’s Criminal Division in Boston. I framed the class as a search for what it means to be a great prosecutor.

I suspect some of you may be thinking right about now that “great prosecutor” is an oxymoron. You’re not alone. Included in our readings for the semester was a chapter from Georgetown Law Professor Paul Butler’s book, Let’s Get Free, A Hip-Hop Theory of Justice. For Butler, and others too, “prosecutors are more part of the problem than the solution. The adversarial nature of the justice system, the culture of the prosecutor’s office, and the politics of crime pose insurmountable obstacles for prosecutors who are concerned with economic and racial justice.”

Butler was a visiting professor at Harvard Law School a few years ago, and we happened to be assigned offices next to one another. We had several great conversations. He gave me an autographed copy of his then-new book, Chokehold, which I read, and which led to an email exchange about Dr. King, hope, bus driving at Duke University, The Youngbloods' song Get Together, prison abolition, and much more. Suffice it to say I admire Butler, but I disagree with him about prosecutors. They can be great. The obstacles to greatness may indeed be many. But they are surmountable. And we should try – and encourage the young – to do it.

Heratch Photography

In class over the course of the semester, we grappled with defining the job of prosecutor. We tried to articulate all of the prosecutor’s various objectives and goals, the tasks they undertake to meet those goals, and the difficult decisions they have to make in the process. These tasks and decisions, of course, are of great consequence to many people.

During the semester, we also met and heard from some very bright and well-meaning people with very different takes on these roles, tasks, and decisions: the Acting United States Attorney, an interdisciplinary expert on criminal law, social inequality, and the legal profession, Assistant United States Attorneys, an Assistant Federal Public Defender, a federal judge, a local district attorney, a former governor.

We talked, over the semester, about charging policies and using informants, managing information and evidence, discovery obligations and sentencing, race and restorative justice, investigations, plea bargaining, why cases end up in federal court sometimes and in state court others, a prosecutor’s ethical responsibilities, and what is justice. We covered a lot of ground and simultaneously just scratched the surface.

In class on that Tuesday, we used a case study to try to better understand – deconstruct and reconstruct – the role of the prosecutor. The case involved the tragic fentanyl overdose death of a 19-year-old University of North Carolina freshman business student named Grace Burton. Burton was on a date with a Duke student, Patrick Rowland, whom she had met on Tinder, when she overdosed. The two had purchased cocaine from a Durham man, Cye Frazier, and unbeknownst to anyone, it contained some fentanyl. When Burton and Rowland, who himself was a campus seller of cocaine and marijuana and knew Frazier well, both began to overdose, Rowland called Frazier, not paramedics. Frazier came back to the Duke campus and carried Burton to Rowland’s dorm room. It would be a while before paramedics were called. Burton died two days later in Duke University Hospital.

We imagined ourselves alone in the moments after the case was first assigned to us. We thought about what we would do next. Do we – and, if so, how do we – craft an investigative plan for the case? What steps do we take to ensure that all the information and evidence that was already being generated – and that would be generated over the coming months – is captured and inventoried so that both inculpatory and exculpatory information is not lost or overlooked? How do we craft an effective and appropriate relationship with our law enforcement partners?

We thought about how we could support Burton’s mother, who raised her as a single parent and was grieving beyond measure (as well as pondering whether that was even our role). We asked why this case was brought to the U.S. Attorney’s Office in the first place. We thought about how we would research the substantive, procedural, and sentencing law so we would have the foundational understanding to help lead the different phases of the case and all that was to come.

We contemplated what a restorative justice approach to this case might look like and what steps we would need to take if that’s where the case might end up. We thought about the Attorney General’s charging and sentencing policy and the office culture in which we worked. And we talked about why the press coverage of the case portrayed Burton and Rowland, white college students, as three-dimensional people, with families, histories, communities, aspirations, and dreams, and portrayed Frazier and his girlfriend, both of whom are Black and both of whom would be charged and convicted for drug trafficking resulting in death, only as two-dimensional drug dealers with criminal records.

Most importantly, we talked about how young people like them could prepare themselves to face a monumentally difficult case like this, a case with life-changing implications for so many. There’s no one way to be a great prosecutor, I suggested, but many different ways. In 1940, in a speech at a conference of U.S. Attorneys delivered at the Main Justice Building, Attorney General Robert Jackson said the same thing in a somewhat outdated way, “[t]he qualities of a good prosecutor are as elusive and as impossible to define as those which mark a gentleman.”

One thing is for sure: a great prosecutor has a genuine understanding of the vast and often-anguishing effects of a criminal investigation or prosecution for all kinds of people. With that understanding, and with some self-reflection — through solitude, as Sixth Circuit Judge Raymond Kethledge implores of us in his book, Lead Yourself First: Inspiring Leadership Through Solitude — and a bit of courage and mercy too, there’s much good that can be done, even through a tragedy. We tried to model that self-reflection in class without veering into so much pondering that we can’t act. We each tried to figure out what we believe in. What kind of prosecutor we want to be.

Our country needs good people to be great prosecutors. It’s a very hard job. But it’s a critical one. A society can’t function without effectively addressing misbehavior. It will start to break down. We’ve seen it before and more recently too. And misbehavior can’t be addressed humanely and justly without each person having inalienable rights that erect a burden for the government before it can punish. The prosecutor is a natural outgrowth of those human and civil rights. Great prosecutors internalize that.

I was at a meeting the other day with a civil rights leader I have known for many years, whom I greatly respect. His words at the meeting suggested that he was, in these times, feeling a bit of despair. Lord knows that as we face 2025, there’s good reason for some to feel despair. But I told him I want to be hopeful. I told him about my class and about being around these young people. They are the hope, the future, the energy we need. They are the antidote to cynicism and distress. They have a lot of passion – for justice and fairness, for what's right, for when it’s time to take on the status quo. We, and they, need to do everything we can to make sure there is still honor in public service. We need to have the courage to see past competition, existing patterns and culture, and politics, and to envision moral greatness – in prosecution, and all manner of public and not-public service – and then to find a way to try to make it happen.