I was a death row lawyer. Here’s why I now joke about capital punishment

2 hours ago 5

The first time I came out as gay to a client on death row, he said: “Josh, I don’t care what you do with your ass, as long as you’re helping mine.” That joke did something legal arguments and moral philosophy rarely could: it made him impossible to keep at a distance.

I spent seven years working as a lawyer for men on both Alabama and federal death rows. I stumbled my way into it. I was only 24, fresh out of law school and working at a big corporate law firm in Manhattan. A friend from law school asked if I wanted to join two pro bono death-penalty cases. I had no relevant experience and knew nothing about capital punishment.

I was, after all, a fresh-faced gay Jewish kid from the Boston suburbs. What did I have to offer a man awaiting execution?

My friend wouldn’t hear it. She told me the clients were really nice, there were interesting legal issues, and I would have the opportunity to work with an important partner at the firm. Those seemed like pretty good reasons to join the team.

One of my first tasks was to review the evidence the prosecution presented at trial. One piece of evidence demanded my attention: a 30-second surveillance video. I spent hours studying those 30 seconds. I knew every damn frame. Something was just off. Then it clicked: it was not a video. It was a slideshow. The surveillance camera had captured a series of still images, which the prosecution presented as continuous footage. That footage had huge gaps that the jurors unconsciously filled in.

The “video” was extraordinarily misleading. The government’s conduct was unconscionable. I was hooked.

During one of my first visits, after some light panicking and a full-body pat-down at the prison entrance, I sat down across from a strongly built, baby-faced Black man in his mid-30s.

Before the visit, the prison had told me not to wear khaki. Now I understood why. He wore a khaki prison jumpsuit over a white undershirt. The guards did not want to mistake a lawyer for a prisoner. He was covered in tattoos, including one of a woman’s name stretched across his neck.

I introduced myself and asked how he was doing.

“I’m blessed, I can’t complain. Doing better than Muammar Gaddafi,” he replied.

I was delighted. Five minutes earlier, I had been terrified of saying the wrong thing. Now, we were laughing about whether it was worse to be on death row or to be a slain Libyan dictator.

That instinct for humor in an unspeakably harsh context was not unique to him. Another client of mine had made several attempts to take his own life. After one such attempt, a correctional officer gave him a pamphlet of yoga poses and mindfulness exercises. He mailed me the pamphlet and wrote across the top in all caps: “NOT WORKING! :P” Even in despair, he wanted me to see the joke.

The death penalty depends, in part, on keeping the people it condemns abstract. Knowing them, and laughing with them, made that distance impossible to maintain.

It was often my clients’ humor that made them impossible to flatten. They were people convicted of terrible crimes, but no verdict could account for the whole person. Many of them had spent more than 20 years on death row accumulating friendships, frustrations and routines. They could be funny, perceptive and infuriating all in the same conversation.

One of my former clients has spent decades in solitary confinement. Locked away in a tiny cell whose narrow window is frosted over, he has become a prolific artist. He makes abstract, distorted figures he calls his “Sassy Boys”. They have tiny hats, canes and earrings. They’re always late and unbothered.

He says they’re like jazz: either you get it or you don’t.

Watching him make work that strange and alive from his cell made it harder for me to justify postponing the life I claimed I wanted.

I began performing standup and improv around New York City. Public speaking did not bother me much, but I was no theater kid. I made friends laugh in conversation, but doing it intentionally was different. What excited me most was the immediacy. A court could take months to issue a ruling on my brief. In a single breath, an audience could reject my joke.

During the day I was fighting to get people off death row. At night, I was improvising a scene in a firehouse where the firefighters greeted one other by saying “lesbians”. Comedy offered an outlet, a community, and a place where the stakes were low.

Bryan Stevenson’s book Just Mercy in particular had shown me how storytelling could bring audiences closer to the people the legal system reduced to verdicts. As I spent more time performing, I began to wonder what comedy might do differently – not by making the subject lighter, but by helping audiences remain engaged when the subject became uncomfortable. I started telling jokes about the death penalty, wondering whether humor could bring audiences even a fraction as close as my clients’ jokes had brought me.

My clients’ jokes revealed the people inside the system. My own jokes often revealed the system’s grotesque logic. I began telling a joke about mitigation evidence: the information that defense lawyers present to help a judge or jury see a life larger than the crime.

The uncomfortable truth was that the more horrific the information we uncovered about a client’s life, the more useful it became for his case. After an interview with a client’s cousin, I called another lawyer on my team: “I have amazing news. He was molested! The dad AND the uncle.”

In ordinary conversation, talking about the death penalty often made people shut down. But even in noisy comedy rooms, audiences listened. After shows, people came up to me with questions about the cases and the system. The laughter did not trivialize the subject. It gave me permission to keep talking about it, and seemed to give them permission to keep listening.

I eventually decided to leave the law. I was burned out. When the stakes of work are literally life and death, it becomes hard to keep the rest of life in proportion.

Still, leaving felt like a betrayal of my clients. I dreaded telling them. But the goodbyes were anticlimactic. They had seen lawyers come and go before. I have stayed in touch with several of them, and I think about them all the time.

After years of treating control and expertise as the highest virtues, I wanted to learn how to fail. So I left for France to study at École Philippe Gaulier, the clown school where Sacha Baron Cohen and Emma Thompson studied. The school taught that a performer’s cleverness is not enough. Audiences respond to the pleasure a performer takes in being on stage, especially when things go wrong.

The teachers were ruthless in their criticism. “Change completely!” they would yell. “Do you hear anybody laughing? Why do you keep doing the same fucking thing over and over if nobody is laughing?”

As a lawyer, I had spent years making sure I had a plan for every contingency. At Gaulier, I began to see how the instinct that had served me as a lawyer could stand between me and an audience. Uncertainty, it turned out, was not a weakness. It was an invitation.

Legal advocacy is essential. A single filing could be the difference between life and death. But after years of working case by case, I became increasingly interested in reaching people for whom the death penalty could remain safely abstract. A court can overturn a sentence. But a legal ruling cannot dissolve the emotional distance that allows executions to remain politically possible.

Comedy offers another way to lessen that distance. Not by lecturing an audience toward a conclusion that took me years to reach, but by letting them watch me stumble toward it through the contradictions, jokes and relationships that changed me.

I do not know whether laughter can change someone’s mind. But a joke can unsettle an assumption and make indifference harder to sustain.

A few weeks ago, the former client who makes the Sassy Boys called and suggested we make a musical. Not to make a political point. Just because it sounded fun to make something with another person. With me.

I can’t sing. But you may see a death penalty musical coming to a theater near you.