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Unfinished Business

Reckoning with the lives of all the men I sent to prison is a necessary, though not sufficient, step to reckon with the untold harm of mass incarceration.


In 2011, when I retired from the United States District Court in the District of Massachusetts, I started writing a book. My idea was to write about sentencing, not in law review articles, or academic commentary. I wanted to write for a lay audience about the actual work of sentencing the human beings who had appeared before me — what I knew of them, the decisions I made, how they should have been treated in a humane criminal legal system, and how they were not. Not even close.

All judges say sentencing is the hardest part of their job. For those few of us, like me, who had been criminal defense or civil rights lawyers, it was simply excruciating. I was a judge at a time when the American criminal justice system went off the rails. We became more punitive than we had ever been in our history, when we imposed punishments harsher than any other country in the Western world, when we were mired in what some have called our failed experiment in mass incarceration. It was a time of mandatory minimum sentences and mandatory “guidelines,” when pretty much all that mattered was what fit within the guideline categories — boxes, really — about the crime, such as how much drugs or how much money, and a person’s criminal record. There was no consideration given to addiction, trauma, mental health, the impact of imprisonment on families, on communities, or much of anything else. This was when Congress stopped asking what works to deter crime and literally picked round numbers out of the air — sentence lengths 5, 10, 15 years. And if we are really mad, life. Indeed, the very year I became a judge, the federal death penalty roared back from the brink of extinction, revived by 1994 legislation. From the moment I ascended to the bench to my very last day, I could not shake my horror at the laws I was obliged to apply, even as I was applying them. 

Of course, it is easy to rail against these laws — in an article, or a well-placed opinion piece — but then wring your hands in each and every case. “I have no choice,” you might say, as you brought down the hammer over and over again. I wasn’t satisfied with that. There was always choice — from the procedural (how much time to give the lawyers to make their case) to the substantive (how to interpret vague rules, or apply general laws to specific facts). There had to be a way to reconcile my oath to enforce these laws, and the demands of humanity, even empathy. 

From the moment I ascended to the bench to my very last day, I could not shake my horror at the laws I was obliged to apply, even as I was applying them.

I started by rereading Professor Robert Cover’s description of Northern judges before the Civil War in Justice Accused. Cover writes about the judges who returned escaped slaves to their owners, enforcing the federal Fugitive Slave Act far more rigorously than they had to despite their own anti-slavery beliefs. Like those judges, would I feel the pressure to act firmly against type by imposing harsh sentences just to prove my neutrality? How would my experiences as a criminal defense lawyer figure into my judging? I had seen those men, visited those prisons, heard the resounding clang of the doors locking behind you, the smell of prison antiseptic, the noise of people shouting to get attention, the cries of the children left behind. Why shouldn’t I look for wiggle room in the laws, other fair legal interpretations that might also be more just or humane? Why shouldn’t I look for the lawful — yes, lawful — ways to mitigate the harsh punishments the government demanded?

Those tensions caused, to put it crassly, a 17-year bellyache. That’s what I wanted to surface. What did I do to the people I sentenced? And more importantly, what should I have done? Some of my judicial colleagues warned me about this project. It meant pulling back the Wizard of Oz’s curtain, watching the sausage being made. Worse, it risked delegitimizing a judicial career of which I was proud. Still, I believed it was critical to talk about what happened to our criminal legal system — how we treated human beings as categories and reduced judges to functionaries, to make sure that we never do it again.

Where to begin? I would start with the files I kept on everyone who came before me during my judicial career — to chronicle what happened to them and why. But my files were incomplete, the facts filtered through the presentations of harried public defenders, prosecutors who defined humans in terms of their crimes, probation officers who fit their complex lives into the federal sentencing grid. Worse, the court documents mainly recounted their failures, the rules they had violated, the sentences they served. Not much else.

Then just by accident, while I was scrolling on Facebook Messenger — in all honesty, an app I had just figured out — I got this message: 

“Is this judge Nancy Gertner? If it is then I hope you remember me…You have been in mind a lot over the years. I always wondered how youre doing. I hope life is well with you.  You are a very special person and I hope you are enjoying all that life has to offer. Peace and love.”

He signed his name. I knew just who he was. He had been a defendant in my courtroom in 2002, charged with murder, a potential death penalty hanging in the balance. We agreed to meet. 

That meeting led to others. I met some of the men in restaurants in Harvard Square, in the cafeteria of the federal courthouse, in my downtown office, in an East Boston classroom. I saw another in a Starbucks just off the highway in a suburb south of Boston. I visited one man in a federal prison in northern New Hampshire, three-and-a-half hours away. They were taller than I remembered. I am short, but my perspective was skewed; when I saw them last, I was on a platform, in a judicial robe. Candidly, I didn’t recognize them. It had been 20 years or so. It was like meeting someone from your past and looking twice to see the young man in the older face. As it turns out, I never knew them well at all. 

I didn’t think any of them would want to talk to me. They would mistrust me just as they mistrusted police, probation officers, sometimes their own lawyers. And how would I begin?  “Hi! I am Nancy Gertner, the judge who sent you away for 10 (or was it 20?) years!”

I was astonished by their reactions. But above all, deeply, deeply moved. Can I talk to you? Sure? Can we meet? Of course? One told me that friends in the neighborhood kept asking, “Has Gertner called you? Call her!” Men reached out to me whose cases I had not intended to include in this book. I would meet with them all, our relationship evolving from judge-defendant to something else. I am not sure how to describe it; there are few models. 

They told me what it felt like to be prosecuted by the federal government in a United States courthouse they never knew existed. They talked about their reactions when they found out that they were facing prison terms double and triple what they risked in the state system. They told me about going to prison far from home, in places they had never heard of. And they told me what happened after they were released — what we euphemistically call reentry — into a world of which they may never have really been a part. These were not the staged presentations about remorse I had heard in the courtroom, often written by the lawyer. No, this time around, we just talked.

Funny, while I was furious about the way they were treated — let me be clear, the way I treated them — they were not. They were not angry at the system that demanded inhumane punishment. Or the prosecutors who mirrored the public’s endless appetite for punishment. Or their lawyers. Or me. 

With these conversations, the book I set out to write took a different turn. It was not only about what I knew about these men when they were before me during my judgeship, what I did when I sentenced them, what I should have done. It was now about how little I knew about them, how much I missed, how distorted was my vision. All of our visions.

Incomplete Sentences delves into only a small selection of the cases I handled in a 17-year judicial career. It presents the stories that shocked me most and lingered years and years afterwards. There were more, many more, but if I told story after story of disproportionate punishment and cruel results, the effect would be numbing. No one should be misled: These were not aberrations in an otherwise fair system. They were the system. By the time I left, the pattern was clear. I had sentenced hundreds and hundreds of men (mostly men) to sentences 80 percent of which I came to believe were unfair, unjust, and disproportionate. 

No one should be misled: These were not aberrations in an otherwise fair system. They were the system.

Make no mistake: I tell these stories now not as a judge would, trying to evaluate “credibility.” Or as a journalist might, trying to uncover the truth. I know there is another narrative that my portraits ignore, the one the government intoned, the one the media parroted, of communities disrupted by drug dealing, of the victims of violence. No, what I am doing is different: I want to chronicle what they have told me, when their sentences were over, when they had nothing to lose, because their voices should be heard. And then I want to understand whether I, the judge, or others in the system, should have listened to them more before we threw the proverbial book at them.

In Just Mercy, Bryan Stevenson repeated his grandmother’s admonition before he embarked on his storied civil rights career. “You can’t understand most of the important things from a distance. You have to get close.” Getting proximate is what he calls it. Getting proximate to the unfairly judged.

Judges are not supposed to get proximate, or so the ethical rules tell us. But writers can. And so I did, after I had left the federal bench. On the other side of a table — over a cup of coffee, a meal — everything looked different than it had when I was “the judge.” I thought sentencing these men was hard; these conversations were worse. The only solace was that they knew — or rather, they said — that I had treated them with dignity, trying to impose sentences that reflected their humanity despite the inhumanity that surrounded us.  

That was not enough for me. It shouldn’t have been enough for them. And for the rest of us, it is, at best, only a start. 

This essay is adapted from the author’s forthcoming Incomplete Sentences (Beacon Press), a judge’s reckoning with a life as a sentencer in the age of mass incarceration. Used by permission.

Image: Unsplash