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

In my standup, I’m not trivializing the death penalty. I’m getting people to stay engaged when the subject is uncomfortable The first time I came out as gay to a...

AAdmin
August 4, 2026
4 min read
I was a death row lawyer. Here’s why I now joke about capital punishment

Josh Pickar: ‘What excited me most [about standup] 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.’ Illustration: Guardian Design/Photo by Steve Ullathorne View image in fullscreen Josh Pickar: ‘What excited me most [about standup] 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.’ Illustration: Guardian Design/Photo by Steve Ullathorne Comedy I was a death row lawyer. Here’s why I now joke about capital punishment In my standup, I’m not trivializing the death penalty. I’m getting people to stay engaged when the subject is uncomfortable

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?

It was often my clients’ humor that made them impossible to flatten 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.

Read more 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 cap…