Removing the judicial mask: Judges tell the stories behind their most trying decisions

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Illustration by Sam Ward

This is my best recollection of events from some years ago. It is a story nevertheless—the memories are shaped by the telling.

A friend whom I had known since college, previously a young public defender, was appointed as a trial court judge in Connecticut. She was sitting on her initial rotation in criminal court when I met her for lunch. I came early and observed her on the bench, presiding at a sentencing hearing. 

A tough case. The defendant had been convicted of vehicular manslaughter; he had been intoxicated while driving, and his car struck and killed a young mother who had been crossing the street after shopping.

The defendant’s attorney argued that this was an exceptional case, and the defendant should receive probation and be placed in a private treatment program as an alternative to incarceration. A combat veteran who had recently returned from multiple deployments overseas, the defendant suffered from severe post-traumatic stress disorder and self-medicated with alcohol. His attorney evoked profound sympathy for his client, who was, in many ways, a tragic figure: a combat veteran whose sadness and remorse were compounded by his guilt over “the accident.”

I do not recall what the prosecutor said or whether he proposed a recommended sentence. I do remember that the victim’s sister spoke eloquently of her sister’s beauty, kindness and generosity of spirit, and how the victim’s young daughter would now grow up without a mother. The victim’s extended family wept throughout the proceedings. There were many attorneys from the local criminal defense bar in the courtroom, apparently interested in evaluating the new judge and the sentence she would hand down in this difficult case.

She looked directly at the defendant and spoke with great strength and authority, without revealing any hesitancy or self-doubt about the multiple factors that had informed her sentencing decision. As I recall, she imposed a tough sentence of incarceration—in the middle-to-upper range of the sentencing guidelines—and required the defendant to successfully complete an in-facilities treatment program. While her words were heartfelt, I believed they were incomplete; her newfound mask of judicial authority covered any of her doubts or reservations as she delivered her sentence.

At lunch, the young judge, typically extroverted and ebullient, seemed unusually circumspect. We did not talk about the case. She apparently did not want to revisit what had transpired in the courtroom. I wondered whether it had mattered that so many attorneys were in the courtroom. As a young woman and a former public defender, did she shoulder a burden to prove her toughness and authority? She was a young mother herself. Did she identify unconsciously with the victim and the plight of the victim’s daughter? Did these unacknowledged cultural factors somehow influence her sentencing decision?

After lunch, the judge returned to her courtroom and to other cases on her docket. I’ve often thought since then about how difficult it is to be a “good” (i.e., fair-minded, ethical, legally rigorous) trial judge. It must be lonely and emotionally excruciating work at times.

What private stories must judges tell themselves so that they are not haunted by and can live with their often discretionary and godlike decisions?

More ‘Tough Cases’

In a remarkable new book, Tough Cases: Judges Tell the Stories of Some of the Hardest Decisions They’ve Ever Made, 13 trial judges (from criminal, civil, probate and family courts) remove their judicial masks and look back, retelling complex stories of their most difficult cases. All 13 judges speak with candor and sometimes write with the intimacy of a confessional memoir.

These are, of course, factually meticulous stories. But they are stories nevertheless—tales that are filled with vivid characters, high stakes, legal dramas, strong plots, and often deep internal conflict within the characters of protagonist judges as they seek to find and deliver justice.

Fundamentally, there are two types of cases. One type consists of several high-profile cases, in which the judges cast themselves in the role of heroic protagonist. The right legal decision is apparent, and the hero judge must courageously stand up to external pressures to preserve judicial integrity and the rule of law.

For example, Florida Circuit Judge Jennifer Bailey recounts how she had no choice but to return young Elian Gonzalez to his father’s custody in Cuba after his mother drowned at sea, despite the public furor and political outcry to keep Elian in Florida. Likewise, in accordance with his understanding of Terri Schiavo’s desires, now-retired Florida Circuit Judge George Greer finds that he had to allow Schiavo—comatose and in a persistent vegetative state—to die, despite overwhelming political, religious and popular pressures to do otherwise. In making their decisions, these judges placed their professional lives, and sometimes their personal safety, at risk.

But the more compelling stories in the book are the second type: the complex, character-driven narratives in many lower-profile cases where the character of the judge is tested when faced with making excruciating, difficult and discretionary choices. 

For example, D.C. Superior Court Judge Russell Canan admits to making the wrong decision in one of his most difficult cases. Canan begins his story this way:

“What the hell, I thought: I reread the note from the jury in chambers. ‘If we find the defendant not guilty of Assault with Intent to Kill While Armed, can we still find him guilty of Assault with a Dangerous Weapon?’ ”

The story turns on Canan’s misunderstanding of the implications of the jury’s question during deliberations in a criminal case. After reading the note, he believes that the jury will convict the defendant of the charge of assault with a dangerous weapon and, more importantly, of a third charge, possession of a firearm during a crime of violence.

The latter charge carries a mandatory five-year sentence. Canan does not believe the defendant is guilty of any crime whatsoever and fears that he will be compelled to send the 40-year-old father of young daughters to prison for a crime that he did not commit and that the prosecutor has not proved. Perhaps Canan even carries some personal responsibility for the defendant’s predicament, since he could have granted the defendant’s motion for a judgment of acquittal at the end of the state’s case. But he did not do so, allowing the case to go to the jury. 

To prevent the defendant’s incarceration, Canan pushes for a last-minute plea bargain before the jury returns with its verdict, although local rules prohibit judicial intervention in plea-bargaining negotiations. Pursuant to a last-minute deal, the defendant would plead guilty to one charge that carries no mandatory minimum sentence, and Canan would then exercise sentencing discretion and place him on probation. 

After the defendant grudgingly changes his plea to guilty—and after Canan accepts his plea—the judge learns from an abandoned verdict form discovered in the jury room that the jury was going to find the defendant not guilty of all charges. “I had orchestrated a turn of events that scared Sam [the defendant]—at the threat of five years of hard time, and with the unsaid promise from me that he would not go to prison—into pleading guilty to something I felt he did not do,” Canan writes. “I had crossed a line to do the right thing under severe pressure in exceptional circumstances.”

The opportunity for storytelling enables Canan to look back and recover a painful lesson from his mistaken judgment. The implicit coda of his cautionary tale: The well-meaning judge comes to a wrong decision when he values a just outcome over adhering rigorously to procedural rules and learns about the dangers of trying to achieve rough justice in a difficult case.

Why these stories matter

The introduction to Tough Cases states that the book’s purpose is “to demystify judicial decision-making and to make the process accessible to ordinary people, who would not otherwise get a ringside seat.” And here the book succeeds magnificently. 

These judges do what my friend, then a recently appointed judge, would not do: remove their professional masks and speak honestly in their own first-person storytelling voices. In doing so, Tough Cases provides 13 eye-opening looks into what it truly means to be a trial judge and reveals how we all find meaning in our professional lives through the stories that we subsequently tell about the work that we do.

Related podcast

The Modern Law Library: “3 trial court judges discuss the some of the hardest cases of their career”

Philip N. Meyer, a professor at Vermont Law School, is the author of Storytelling for Lawyers.

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