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A Conversation with a Federal Judge About the ‘Serious, Serious Problems with Our Legal System’


Judge Jed Rakoff

Judge Jed S. Rakoff of the Southern District of New York is, and always has been, a very busy man. He is in his courtroom early, late and throughout the COVID-19 pandemic. He has served on the MacArthur Foundation’s Law and Neuroscience Project and as co-chair of the National Academy of Science’s Committee on Eyewitness Identification and has taught at Columbia Law School for more than 20 years. Judge Rakoff was appointed to the U.S. District Court for the Southern District of New York in 1996 by then-President Bill Clinton. Judge Rakoff assumed senior status in 2010. In his spare time–and in addition to his more than 1,800 (sometimes controversial) opinions–he has coauthored five books, published 170 articles, delivered over 700 speeches, and is a regular contributor to the New York Review of Books. Given his opinions and writings, Judge Rakoff is likely the most prolific trial judge in America.

He has, now, authored a new book, provocatively titled, Why the Innocent Plead Guilty and the Guilty Go Free: And Other Paradoxes of Our Broken Legal System. Joel Cohen interviewed Judge Rakoff on February 16, 2021 to talk about some of the more troubling subjects Judge Rakoff has tackled in the book–and in his courtroom (Cohen’s questions are in bold and the judge’s answers are not).

Judge Rakoff, thank you for your illuminating book. Let me begin this way: newspapers compose headlines designed to have people read the articles. Book sellers write titles to encourage people to buy books. Maybe that’s the purpose of your title, and the title is somewhat worrisome. It’s troubling when innocent people plead guilty. Also when the guilty go free (although less so). But your subtitle presents something far worse–it says that you work in a broken legal system. You go daily—even, I’m told, during COVID times—to a courthouse that ministers a “broken” legal system. Is that it – a broken legal system?

There are serious, serious problems with our legal system. And I came to that realization in part through what I observed to my own courtroom and those of my colleagues. Still, I don’t think it is unfixable. I’m hopeful that we are at a time in our history when substantial improvements can be made in the respects in which I think the legal system is broken.

As just one example: mass incarceration. The United States leads the world by a substantial amount in the number of people we send to jail and prison. Over two million every year for the last 20 years. And who in the narrow sense sends those people to jail? Judges, including myself. So we are very much part of that problem. But the problem’s basic cause, more than anything, are laws passed by Congress and by state legislatures. So it is not only the judges who are to blame. Indeed, in many cases our hands are tied by mandatory minimum sentences, career offender statutes, guidelines that, while not strictly binding, are very draconian. But I do think that judges, as the people who actually impose the sentences that lead to this mass incarceration, are obligated to tell the American public just how ruinous the system is.

My question, though, is can the system be fixed in the courtroom, or maybe elsewhere? For example, your book mentions that you once declared the death penalty unconstitutional. You were reversed quickly on appeal. The death penalty still exists, although President Biden currently seems interested in doing away with it. But can the courts, trial judges like yourself, do so? You tried with great purpose, but failed. So can the courts actually repair injustices—the death penalty, as a good example?

The answer is: some they can, and some not. Taking the death penalty as an example. The Supreme Court has the power to declare it unconstitutional. In fact, they did so in 1972 but on grounds that were then fixed, so to speak, by the states through legislation. And, so, the death penalty was reinstated some six years later. The Supreme Court has been slowly limiting the death penalty so that it’s no longer constitutional to execute someone who is mentally disabled, or below the age of 18. So there’s been a slow cutting at the corners. But I actually think that the citizenry and their opinions can play a big role here. They effectively played a big role in the reversal of the Supreme Court’s original death penalty abolition. But now, in every poll I’ve seen, people are becoming ever more skeptical of the death penalty. And, frankly, I think that’s partly for the same reasons that led me to hold it unconstitutional—the increasing evidence that meaningful numbers of innocents are being sent to the death chamber.

Taking you up on your title’s claim that innocent people plead guilty. That has been, for example, in New York state courts, a serious problem. Defendants waiting for trial in jail actually plead guilty as the best vehicle for their prompt release. It’s less of a problem now because of bail reform largely eliminating cash bail in many cases. But do you fear that innocent people are pleading guilty in federal court, too?

I have had one or two cases where I was sufficiently worried about that so that I made inquiries beyond what would normally happen in taking a guilty plea. But the difficulty here comes from the fact that the plea bargaining system is secret. It’s unrecorded. It occurs totally in the prosecutor’s office. The prosecutor, because of the heavy penalties available depending on the crimes he charges, holds most of the cards; and by the time the parties go before the judge to enter the guilty plea, the innocent person has already made the decision: “Yeah, I’ll say whatever is necessary to get that plea because I don’t want the worse result that may follow if I don’t plead.” In my book, I propose that judges get involved in the plea bargaining review process much, much earlier.

Although it currently violates law for a judge to get involved, correct?

In some states it occurs. It violates federal law, though, because the notion is that judges shouldn’t be involved in negotiations between parties in an adversarial system. They should be aloof until the case reaches a point where a judgment must be entered. To me, that is totally at odds with the fact that 97-percent of all federal criminal cases are plea-bargained, and the result is the judges have declared that they will be absent from where the action is in 97-percent of the cases. It makes no sense to me.

They’re not really absent—sentencing is probably the most important part of most cases. They’re there. Lawyers on both sides get to say what they want, and the judge makes her judgment, or even holds a hearing. They’re not completely absent from the process, right?

No. I think you’re missing the point somewhat. When an innocent person pleads guilty, (and the best estimates, are that somewhere between 5- and 10-percent of all criminal defendants who plead guilty are innocent, so we’re talking tens if not hundreds of thousands of people) the judge in the federal system has no role in that decision. In a few states, Connecticut for example, the judge gets involved immediately after indictment, and gets a chance to separately question the parties as to what their real situation is. By the time it reaches the judge in the federal system, the decision has been made—even by the innocent people—to plead guilty. And let me add that, with mandatory minimums, the judge often doesn’t have discretion even at sentencing to see that justice is done.

Let me turn to the other part of your title: “Why the Guilty Go Free.” An important point in your book and previously in your revealing articles for the New York Review of Books, is that corporate executives in big-time white collar offenses aren’t prosecuted often enough. True?

Sadly, those high-level executives who in my view are often responsible for major frauds have become almost immune to prosecution. That wasn’t always the case. When I was a federal prosecutor in charge of the Business and Securities Fraud Prosecutions Unit in the Southern District of New York, we almost never went after companies. We went after the individuals, because they were the ones who actually committed the crimes. Sometimes they were low-level, but sometimes, they flipped and gave us higher level individuals.

In those days the CEO of Enron; the CEO of WorldCom; and the chief progenitor of the Savings and Loan crisis, Charles Keating, were convicted. That all changed beginning in roughly 2006—and the Justice Department since then largely just goes after the companies, and they think they’re doing their job by having the company pay a big fine and change compliance measures. That’s a very misguided approach.

So if you have a corporate plea or a deferred prosecution agreement presented to you for acceptance, do you tell the prosecutor “Why isn’t the CEO being prosecuted?”

I don’t know that I would have enough information to do that. I have turned down some of those proposed agreements on other grounds. But the heart of this problem lies with the policy decisions at the prosecution offices—that they think that by instituting compliance measures, they are preventing future crimes and that the benefits outweigh the costs.

However, a study has been done on this by Brandon Garrett of Duke Law School called “Too Big to Jail.” He studied every corporate prosecution from the late 1990s through the mid-2010s. And he found a high rate of recidivism, so the compliance measures didn’t seem to be working. As for the fines, they’re usually a small portion of the profits that were made through the crime. So the deterrent effect is modest, and that’s why you have recidivism. By contrast, if high-level executives who were responsible for the fraud, or who consciously winked at the frauds of their subordinates, went to prison, that would surely send the message that would have substantial deterrent effect.

It’s interesting that you won’t tell the prosecutor: “Why isn’t the CEO being prosecuted?” Sort of like paraphrasing Dirty Harry: “a judge needs to know his limitations”?

Every case is different. It’s not like you have dozens of these cases every day. In a case where I did turn down the SEC settlement with Citigroup, I did expressly question why other individuals had not been charged. They named one lower level person and the bank in a fraud that possibly led to hundreds of millions of dollars of losses. But I can’t give you a recipe for when it’s right for a judge to question why someone hasn’t been named.

My point is that judges in these situations are information-deprived, which makes it very difficult for them to play a role as aggressive as they might wish.

I’ll conclude with this question. Typically, when someone is interviewed about a book they’ve written they’re asked: “Why did you write this book?” It seems that given your stature in the judiciary, in writing such a book when you can’t be reversed by a higher court, probably allows you to improve the law in ways you simply can’t as a sitting judge. As a judge you have a case before you. Presiding over it confronts certain restrictions or limitations—although you sometimes like to push the limitations to the outer edge. And I say that as a compliment. But you can’t do some things in a courtroom that you might like to do. You’re not so limited in writing a book.

You hit the nail on the head. The code of conduct that governs all federal judges (except, ironically, Supreme Court Justices) says in Canon 4 that judges may write about problems they perceive with the administration of law, broadly defined. And the commentary to Canon 4 encourages judges to do so. I believe that I was negligent in not taking that to heart sooner. I didn’t write my first article until I was on the bench for 14 years. And this is my first book, other than technical books.

I think the reason Canon 4 encourages judges to be more outspoken about problems they see in the administration of law is precisely what you just said. There are limits on what we can do as judges. But we can bring to light the problems we see and hope that the public, the legislatures and the administrators, as well as our fellow judges, will be influenced to take further steps.

That said, and with the passage of time and more thoughtful, persuasive, works like yours, perhaps the subtitle of your book’s second printing can be altered to refer to a “Repairing (No Longer Broken) Legal System.”

Thank you. Judge.

Joel Cohen practices white collar criminal defense law at Stroock & Stroock & Lavan, LLP. He is the author of “Blindfolds Off: Judges On How They Decide”(ABA Publishing, 2014) and an adjunct professor at both Fordham and Cardozo Law Schools.

[Image via YouTube screengrab]

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