The Sentencing Matters Substack Interview: Former Prosecutor, Adjunct Law Professor, and White House Aid, and Current Criminal Justice Commentator, Bill Otis
I first met 1974 Stanford Law School grad Bill Otis during the Clinton Administration at a meeting in the Solicitor General’s Office to discuss the Justice Department’s position in a case then-pending before the Supreme Court, Dickerson v. United States. Before Roe v. Wade was even handed down, the conservative legal establishment was laser-focused on overturning Miranda v. Arizona. That case, of course, is the Warren Court decision that held that certain warnings had to be given before a suspect’s statement made during custodial interrogation could be admitted at trial. Dickerson was going to be the case to overturn it, and Bill, as the Appellate Chief in the U.S. Attorney’s Office for the Eastern District of Virginia (EDVA), had convinced the Fourth Circuit Court of Appeals that Congress could – and did – essentially reverse Miranda by enacting 18 U.S.C. § 3501, which makes the admissibility of statements such as Dickerson's turn solely on whether they were made voluntarily.
But then-Solicitor General Seth Waxman and Deputy Solicitor General Michael Dreeben saw the case and the constitutional questions differently. The ensuing meeting about what position to take in the Supreme Court was tense and uncomfortable, and ultimately, the Solicitor General reversed Bill’s positions and confessed error – Bill’s error – in the Court.
Former federal judge, now law professor, Paul Cassell argued Bill’s position as amicus curiae appointed by the Court. Chief Justice Rehnquist later wrote the opinion for a 7-2 majority reaffirming Miranda. Justice Scalia, joined by Justice Thomas, dissented, largely adopting Bill's argument. Bill, of course, was disappointed with the outcome of the case and with the Solicitor General's meeting. But as soon as the meeting ended, there were handshakes all around and no ill will.
Bill feels very strongly about criminal justice policy, including sentencing policy. He describes himself proudly as a Goldwater Republican. And he was summed up by Slate Magazine in 2015 as the only person who could stop bipartisan criminal justice reform from being enacted in Congress. On sentencing policy, Bill’s position can be condensed into this simple quote of his from a Federalist Society event: “[t]wo facts about crime and sentencing dwarf everything else we’ve learned for the last 50 years: when we have more prison, we have less crime. And when we have less prison, we have more crime.”
But while Bill’s views on crime are at one end of the ideological spectrum, his friendships span it. He proudly told me that his best friend – and the best man at his wedding – was, in law school, a Marxist who had participated in the takeover of the Dartmouth Administration Building during the Vietnam War era. Bill respects honesty – especially intellectual honesty, which he views as the foundation of learning – detests corruption, and cherishes his friendships, which have respect at their base.
Bill spent most of his career as the Appellate Chief in EDVA. He had stints at the White House Counsel’s Office and the Drug Enforcement Administration. He was nominated with three others – all federal judges – to the U.S. Sentencing Commission by President Trump during his first Administration, but neither he nor the other nominees reached a floor vote. He has been a commentator on crime and sentencing policy for decades and writes on the Substack newsletter, "Ringside at the Reckoning."
I wanted to talk with Bill as the new Trump Administration was readying to take the reins of power to hear his views about where issues around sentencing policy stand on this 40th anniversary year of the Sentencing Reform Act and 20th anniversary year of Booker, and where sentencing policy might be going next. I spoke with him just before the inauguration.
The interview was lightly edited for clarity and brevity.
Jonathan: Bill, it’s good to see you. Thank you so much for sitting down with me. Before we get to sentencing policy, could we start with the beginning of your career. What went into your decision to attend Stanford Law School and why did you decide to join the Justice Department after graduating from Stanford in the 1970s?
Bill: I was casual about selecting a law school. For me, it was mostly like flipping through a magazine. I saw pictures of Stanford's beautiful red tile roofs, the Spanish sandstone architecture, the surrounding countryside. Wow! This place looks wonderful; and it’s warm, too. That was pretty much it. And it was an exotic feel being in the Bay Area back then. It was a good education, and I was able to get the job I wanted.
Why the Justice Department? I’ve always felt that the Justice Department wore the white hat; that they were the good guys, and the bad guys were harming people, stealing stuff, selling dangerous drugs, and making life unsafe and unpleasant for others. I grew up in the 1950s and early 60s, and I had the feeling about government that existed widely then; when trust in government and trust in institutions generally was so much higher than it is now. I grew up watching Dragnet and all the portrayals of J. Edgar Hoover, which were, then, decidedly positive.
Jonathan: Were you hired through the DOJ Honors Program?
Bill: Yes. I was lucky to get my preference, and I was hired into the Criminal Division. I wanted to be like Perry Mason, a trial lawyer. But I was assigned to the Appellate Section. It turned out to be a good break mainly because my bosses at the Appellate Section, in particular the late Jerry Feit, were great. They tolerated the bad, self-important parts of me, and encouraged and helped me build up the good parts. They taught me how to be a lawyer. When I came out of law school, I knew very little about how to be a lawyer. They taught me how to behave, how to write, how to present myself. I got to argue before all the circuit courts of appeals.
Jonathan: Why did you decide to move from Main Justice to the U.S. Attorney’s Office? And how different was your experience there?
Bill: The difference between the two was the difference between being in a mausoleum and being in real life. Main Justice even looks like a mausoleum. And, naturally enough, it feels too much like headquarters. The work at U.S. Attorney's office, on the other hand, is kind of a street fight.
The specific reason I went there in 1981 was that there was going to be a new chief in the Appellate Section. The old chief was retiring, and Bob Mueller, then Assistant Attorney General for the Criminal Division, interviewed me for the job. I didn't get it, but Mueller was totally himself, a straightforward ex-Marine. He told me, “Bill, you're the best lawyer I interviewed, but you're not interested in management. I need a manager.” So, I figured maybe my future lay somewhere different. At the same time that was happening, I had been helping out the Eastern District of Virginia, including Karen Tandy, who was then a young AUSA, and Leonie Brinkema, now a U.S. District Judge, who was then Chief of the Criminal Division in EDVA. She and Karen were working on the biggest marijuana case that district had ever had, and as part of it, they wanted to issue a search warrant for a defense lawyer's office. That's a little dicey, and they had to get approval from Main Justice. The case was assigned to me. They were happy with me and my work. I was happy with the environment they did so much to create at the US Attorney's Office. They invited me to come over at just the right time. So, I went over there. I was happy as a clam.
Jonathan: How did you first get involved in sentencing policy?
Bill: Before the Guidelines, I had very little interest in sentencing. Sentencing appeals were extremely unusual. When the Sentencing Reform Act passed in 1984, I had been in charge of appeals for the U.S. Attorney's Office three years. Everybody was afraid of the Guidelines, even though the Reagan Administration – with which I agreed on nearly everything – was behind the Guidelines’ regime. I saw it as this giant ship floating over the ocean in my direction, and Henry Hudson, who was the U.S. Attorney, sensed the same thing.
The ship was not entirely welcome from my point of view. Here are these quite detailed rules (“guidelines” was a misnomer). You have to do complicated calculations. They're mandatory. The judges have to follow them absent good reason explained on the record. And Henry wanted someone to be responsible for implementing this. So, one day he came to my office and just announced, “you're responsible!” I said, “Henry, I don't know anything about it.” Henry just smiled and said, “you'll figure it out.” That was his management style. So, I wound up with an entirely new, additional job trying to dope out a revolutionary system, the biggest change in federal criminal law in my career and perhaps ever. They were certainly going to make my job different, because now all the defendants were going to appeal their sentences even if they had pleaded guilty. Indeed, the defense bar put on seminars about litigating the system into the ground. The bench liked the Guidelines even less, because they cabined courts' previously almost unbounded discretion. AUSAs didn’t like them at first either, because you had to learn a bunch of brand-new rules. I had to learn them well enough to teach them, although I was actually quite skeptical of them initially. My colleagues in the U.S. Attorney's Office and I, of course, came to like them a lot and were happy to defend them.
In particular, my friend, former AUSA Judge Brinkema tended to view most defendants sympathetically; they had a tough life, maybe from a one-parent household, their school was awful and dangerous . . . Her view is not one with which I mostly agree, but it's a view of life that's good hearted and one an intelligent person can adopt. She did adopt it. She would often find reasons to go below the Guidelines. I would find reasons, mostly successfully, to appeal. In part because of Judge Billy Wilkins, the Sentencing Commission's first chairman, the Guidelines were popular in the Fourth Circuit then, and if you were a departing district judge, you were probably going to wind up on the losing side. I was proud that, partly on account of this, the Eastern District of Virginia achieved one of the highest Guidelines compliance rates in the country.
Jonathan: So, we're approaching the 20th anniversary of the Booker decision, which brought another dramatic change to sentencing. What did you think then when the decision was handed down, and what do you think of federal sentencing policy today?
Bill: I thought the opinion on the merits – that the Guidelines as formulated were unconstitutional – was problematic, and the remedial part of the opinion was not merely problematic but disastrous. As Justice Stevens wrote as the lead author of the four-justice dissent, the Court's majority instituted a remedy – making the Guidelines advisory only – that was exactly the opposite of what Congress intended in adopting Guidelines. What should have been the remedy – assuming that the merits part of Booker was correct – was to require the government to prove important sentencing facts beyond a reasonable doubt, but keep the Guidelines mandatory.
The “advisory only” remedy all but throws away what I view as one of the major achievements of federal criminal law – making sentencing law-driven rather than taste-driven. That was a seminal advance for the rule of law, one that benefited both sides in litigation, because sentencing no longer depended just on the luck of the draw, the judge that was assigned to your case, and it didn't just depend on the judge's mood or what his political background was, or his ideology. Those things were still present to be sure and still had an effect; you can't be a realistic observer and think anything else. But when the Guidelines were mandatory, the judges were more constrained by actual written-down rules. You could debate them in front of the court and then get at least a rules-based decision, and a decision more subject to intelligent appellate review. That's a better way to do law. In an advisory only system, all that has been left at the side of the road.
Jonathan: You were nominated to the Sentencing Commission twice by President Trump. What did you hope to accomplish?
Bill: The main thing I wanted to do wasn't to make relatively minor adjustments with this guideline or that, or with one application note or another. Well-informed suggestions for changes of that type can be drafted by the staff. They're smart people, really smart; the Commission staff was the most informed and most helpful federal agency I ever dealt with in my career.
What I hoped the commissioners would address – and what they still need to address – is the system as a whole. I wanted to restore a mandatory system that meets constitutional demands as seen by the Court. That would be done, under Booker, if we had a system under which the government had to prove significant sentencing facts beyond a reasonable doubt. That's the remedy the Court should have chosen, and the remedy the Commission should choose today. Of course a change of that degree would require amending the Sentencing Reform Act of 1984, which established the original framework for the Guidelines, but the Commission would be instrumental in drafting and recommending such a change to Congress. That's the main thing I wanted to do.
Jonathan: Do you have thoughts about the recent movement to allow for so-called “second look” sentencing or review of long sentences, a bit like parole?
Bill: America believes in second chances. People do change. But there’s a big footnote in that: some people change for the worse. Indeed, this is something the defense bar often emphasizes in opposing what it (erroneously) calls “mass incarceration” – that prison is little more than a school for crime. I have my doubts about that, but it raises an important question: what do we think is going to happen when inmates get out early if, as is certain to be true in an unknown number of cases, they've just learned to be more sophisticated and clever criminals?
That won't always be the case, but it sounds a note of caution. My point in bringing it up is that I support second look sentencing to a degree, if it's done with our eyes open and not just as an ideological manifestation of the notion that “we-have-too-much-prison-so-it-has-to-be-cut-back.” Second look sentencing obviously offers a second chance, but we need to think about: a second chance to do what? The next crime victim is not less of a human being and not less deserving of the law's protection because we can't tell who she is right now.
There are people who turn their lives around, but there are also people who don't, and people who get worse. The recidivism rate is extremely high. It would be profoundly wrong to increase the number of future crime victims without a high degree of confidence that a candidate for a reduced sentence will live a law-abiding life.
Jonathan: So do you think there is a role for some second look?
Bill: As you can tell, I don't yet have a full and coherent answer to that. Human beings, including judges, make mistakes. And the defendants they deal with can grow. To ignore entirely the possibility of betterment seems wrong. But my years of talking with the defense bar have bred in me a certain cynicism because, in my experience, defense lawyering is almost always trying to sell some version of “everybody's-just-sick-nobody's-bad.” That's simply not true. Some people are sick and can get better. Some people are both sick and bad. We should offer them help for their sickness and punishment for their badness, because an essential lesson of life in civil society is that actions have consequences. Some people are pretty bad all the way through, and those people need to be in prison for a long time.
Perhaps one way to begin to approach second look sentencing is that we could create a provision in plea agreements that lets the district judge retain jurisdiction of the case. Then at some period down the road there would be a second look. But – and I doubt the defense bar would buy this – the potential change in sentencing wouldn’t be in just one direction. If the defendant has gotten worse, if he's become more dangerous, then I think the court should be able to lengthen the sentence, which it could do legally if the parties agreed to that arrangement from the outset. If the defendant has turned his life around, the sentence could be reduced or, in some cases, ended.
This only seems fair to me. The entire rationale of second look sentencing is that people can change. No serious person doubts that. But since they can change either for better or worse, a second look sentencing regime should be able to adjust the defendant's outcome – up or down – to fit the individual facts about him.
I should add one other thing: The discussion about second look sentencing tends to focus only on the offender and his possible rehabilitation. But that is myopic. Other very important goals of sentencing are just deserts for the crime and honesty with the public in the initial announcement of the sentence. Those are legitimate and important considerations, and any change in our present system is, in some form, going to need to accommodate them.
Jonathan: Three more topics that I’d like you to touch on quickly: the death penalty, plea bargaining, and clemency. Let's start with the death penalty. President Biden just commuted the sentence of everyone on federal death row except for three people, and of course President Trump has said he wants to use the death penalty more. What do you think of all of this?
Bill: I'm in favor of the death penalty. Most Americans are and have been for over 50 years going back to the mid-seventies. A clear Supreme Court majority supports it. The reason for its long and broad support is the simple maxim that the punishment should fit the crime, and there are some crimes so grotesque that only the death penalty even comes close. The Boston Marathon bomber, for example, blew up an eight year-old boy, who bled to death in his father's arms. He knowingly left the bomb at the kid's feet. The ironic and instructive thing is that President Biden, by giving clemency to 37 killers on death row – but conspicuously not three others – implicitly, but clearly, recognized that there are crimes so grotesque, including the Boston Marathon bomber, that the death penalty is appropriate and just.
My other strong reason for supporting the death penalty in clear-cut cases is that our country has the decency and sobriety to have earned the moral confidence to act decisively in the face of evil – to say "no" and mean it. The death penalty is a strong symbol of that confidence.
Jonathan: How about clemency?
Bill: The system is not infallible. Even when you follow all the steps as carefully as you can, the criminal justice system will make mistakes and punish the innocent or over-punish people correctly convicted. (Of course it can and does also fail to punish, or significantly under-punish, the guilty, but that's another subject). Hence the constitutional framework is correct in including a clemency power. The glaring mistake is leaving it entirely to the President. We've seen abuses galore, maybe President Clinton most notoriously a generation ago pardoning his brother-in-law and fugitive donor Marc Rich – although amazingly, of late it's become even worse.
In the first Trump Administration, we had Paul Manafort, a clemency recipient but a crook of breathtaking proportions. If he ever comes to your neighborhood, move. Why does he get a pardon? Because he's become a good person? No, because he's a buddy of the President. Obama had his share, and now Biden tops them all (for the moment) by pardoning his thoroughly guilty son after repeatedly – though only before the election – promising that he wouldn't. He tops this by almost clearing out death row of killers no sane person thinks are innocent. Then the prospective pardons for his political allies.
What does this teach us? That we should retain the pardon power, but it needs major reform. The reform I've proposed – which would require both a constitutional amendment and legislation – is that there would be a seven-member commission. It would consist of two Republicans who were either former attorneys general or former deputy attorneys general; two Democrats, also former attorneys general or deputy attorneys general; and three retired federal judges selected by consensus. That seven-member commission would, by majority vote, recommend clemency candidates to the President. The President could choose anyone or no one on that list, but could not go outside it. The constitutional idea of leaving the ultimate decision to the President would remain, but with this commission weeding out political favoritism, corruption, abuse, and grandstanding.
This is an important problem for our governance. Abuse of clemency is bringing the whole criminal justice system into disrepute. I was talking earlier about how there's so much less trust in institutions, in the government, and in the courts than there was just two generations ago. It’s important to stop it. If people don't believe in the honesty and good faith of the government under which they are living, it will breed a corrosive and dangerous cynicism. Subtracting the political fixes, the obvious “who-you-know-not-what-you-did influence” that's now running wild in the clemency system, has to go. I don't think that's going to happen. But our governance and the civic faith it needs to earn from its citizens would be much better if it did.
Jonathan: How about plea bargaining?
Bill: The bottom line is it would be better if we had the resources for everybody to have a trial. That's what the Framers intended. The Constitution doesn't say a single word about plea bargaining. Yet almost all the cases now – 95% or more – are plea bargained. The basic reasons for that is that every component in the system gets something it values. Defendants and defense lawyers get a lot by the dismissal of many (sometimes most) charges and/or by getting a favorable sentencing recommendation. The prosecutor, even with a strong case, can never be sure about the outcome if he goes to trial, see, e.g., O.J. Simpson. With a bargain, he gets the assurance of a conviction usually with the main count preserved. And the judges are not overwhelmed, something that would happen in short order if all or even most cases went to trial.
But it's crucial to remember this: It's not a conspiracy and it's not a plot. Most criminal cases are settled for exactly the same reason most civil cases are settled. And, I can tell you from decades of experience, the bottom line reason defendants plead guilty is that they are in fact quilty and would lose, and lose badly, if they went to trial. It's not extortion. It's the reality of the evidence.
Jonathan: Thank you so much for sitting down with me today, Bill, and for sharing your thoughts on many important topics.
Bill: Jonathan, thank you for taking the interest in an old buzzard! Thank you too for your patience and courtesy. Most of all, thank you for all you have given over decades of helping improve federal sentencing. You and I tend to see political questions from different angles, but your honesty, open-mindedness, and incredibly thorough knowledge are admired throughout the sentencing world.
For myself, I've been blessed to be able to do this law stuff my whole life. How many people get that? My father didn't. He was from the working class and, though admitted to Penn Law, didn't have the money to go. Because of my parents, my colleagues, and the opportunities our country creates, I got to spend my time learning and thinking and working on stuff that's important. What more can I want in a career?
