“Pickleball Inside and Out” is a collaborative essay/interview between law professor Deborah “Debbie” Zalesne and incarcerated writer Aaron Olson, both pickleball enthusiasts.
Debbie: I play pickleball four or five times a week. I cancel plans for pickleball. Many of my friends are pickleball people now. For me, pickleball is part therapy, part workout, and part social hour. I love the rhythm of it — how you have to react fast but also stay calm. It’s taught me more patience than yoga ever did. But even with all that, I never expected I’d end up obsessing over the game with someone on the inside.
Aaron and I met through a writing program, and somewhere in the middle of talking about stories, family, and memory, we discovered we both loved this addictive game. He plays in prison. I play at local courts and rec centers. But the way we talk about it? It’s like we’re on the same court.
I “sat down” with Aaron to ask him about his experience playing pickleball in prison.
Debbie: How did pickleball find you where you are?
Aaron: I first heard about pickleball when I was eight years old. My mom was dating a man in great shape who looked close to her age — but I later learned he was thirty years older. His secret? “I eat healthy, weight train, and play pickleball.” He explained the game, but I couldn’t get past the word pickle. It sounded strange. Like actual pickles to an eight-year-old, pickleball would turn out to be an acquired taste.
Prison, in many ways, feels like being stuck in high school in an impoverished and over-policed neighborhood — full of gossip, cliques, and daily stress. There’s no vacation, no spa day, no great food, and precious little time with loved ones. That’s where sports come in.
My path to pickleball was really by process of elimination. Basketball? Knee injury. (Pro tip: potholes don’t belong on a basketball court.) Baseball? Shoulder injury from sliding on an uneven dirt field. Handball? Back injury — me thinking I was Superman. Every other sport aggravated those injuries, except pickleball.
I was happily sticking to weight training — something I can do well and without injury — when one day an older gentleman, in great shape, challenged me to a game. Suddenly I was eight years old again, but this time I loved pickles.
The first time I held a paddle, I was hooked. I didn’t care about the name anymore — it was pure fun. I finished my first singles match drenched in sweat and sore the next day, but my body felt great.
Most prisons don’t have pickleball courts. The one I’ve been in for the last thirteen years does, but don’t imagine smooth surfaces and crisp lines. Ours is more like an old parking lot in the part of town you avoid — sixty-year-old concrete near the Pacific coast, weathered by rain, rocks, and broken chunks of pavement knit together like puzzle pieces. The bounces are unpredictable, but we play everything. No do-overs.
Debbie: What does it feel like to play inside the fences? What’s the competition like? Are the rivalries healthy? Is it a way to make connections or maybe even resolve disputes?
Aaron: There are many barriers in prison that stand in the way of camaraderie — race, gang affiliation, crime of conviction, age, religion, sexual orientation, even politics. Many people go along with these divisions because, as they say, “that’s just how it is.” Like Jim Crow, these written and unwritten rules are backed by the correctional system and enforced by select prisoners who don’t welcome change. For those of us who want to buck that system peacefully, the options are limited.
Education can be one safe bridge. So can family visits. Sports, too — but usually only the one-on-one kind. Team sports often reinforce rivalries and escalate conflict. But sports like pickleball offer something rare: a way to cross boundaries without repercussion.
Zero-zero start — and the differences stay outside the lines. The net doesn’t just divide the court, it connects two worlds: Black and white, Christian and Muslim, gay and straight, old and young, lifer and short-timer. On the court, all are equal. Win or lose, everyone walks away having sweated, laughed, and competed — often while battling wind, bad bounces, and concrete that looks like it’s been through a few earthquakes.
My toughest opponent is a man 10 years older than me. I’ll admit it — he owns me. And I’m no slouch. I’m 39 (in November), run a six-minute mile, and rep 225 pounds for multiple sets. I played high school football, and I still pride myself on being in top shape. But no matter how strong or fast I am, he makes me chase the ball corner to corner until my knees and feet are screaming.
Early on, I tried to bring my handball instincts to the pickleball court — keeping to the back line, playing it safe. Big mistake. In pickleball, the net is where the game is won. My nemesis taught me that lesson the hard way. But in pushing me, he also earned my respect. That’s the thing about pickleball: whether you’re playing with someone or against them, the effort, the grit, the fire earns respect. And in here, respect is everything.
Pickleball is a sport anyone can play, but I think it’s best appreciated by people who have lived a little — people with scars, stories, injuries, and resilience, but who still carry that fire to compete.
Debbie: What’s the most memorable pickleball match you’ve played inside — a game you’ll never forget?
Aaron: To us, pickleball is an escape from a 6×8 cell, freedom from forced labor for pennies per hour, and an opportunity to occupy the same space as someone completely different. It’s peace from the court-ordered chaos that is called prison. It’s friendly competition between condemned souls banished from polite society. So the games are memorable when the rivalries and divisions disappear.
“Do you think you’re good?” The voice caught my attention. My last opponent was walking off the court after I picked apart his game (strategy) and successfully beat him in two straight games. It was dark, but the court had an overhead lamp illuminating the net and most of the lines. Into the light walked a man I’d seen several times, but hadn’t spoken to. Jonathan is Latino, I am white. He is gay, I am not. He is an Atheist, I am a Christian. He is a progressive, I lean conservative. These are more than enough differences in prison for us to never associate, and possibly even be enemies with opportunities for violence. “Good enough to beat you!” I replied sharply, the words striking back like a return serve…
He beat me the first game. The ground was wet, and the ball skimmed instead of bouncing. His serves were lasers, and I only managed one point. “I thought you said you were good,” he snickered. My blood boiled, but I said nothing. We played six more games, and I won them all, each one tight and down to the wire. “Why didn’t you play like this the first game?” he asked. “I didn’t think you were as good,” I answered. He replied with my first of many business lessons: “Don’t ever underestimate your competition.” A fact I should know, as prison is wildly unpredictable.
We played almost every day for the next three months, until he was transferred to another prison.
Jonathan was a musician who did well on Spotify, and invested his money wisely. “Business was the only thing I was good at. My personal life was a mess, and prison is the result.” He taught me many things about business, but most importantly, he helped me believe that I can accomplish great things, even from prison. “You were born to be an executive, Aaron! Remember to value the relationships you build, never burn bridges, always outwork everyone else, and just like pickleball, no matter what the score is, always believe in yourself and never give up!”
Who knew that a pickup game of pickleball in a cold, wet Pacific Northwest prison would cultivate an unusual friendship and lessons that would lead to me fulfilling my dreams of publishing, podcasting, earning a degree and becoming an executive of a startup.
Aaron: Now let me ask you something, Debbie. What if you could visit me — would you take me on, or team up with me, for a few games?
Debbie: If I could visit and play with you? I’d jump at the chance. I’d want one game as your partner, just to feel what it’s like to be on your team, and then one game across the net, to test myself against all that speed and strength you brag about. Fair warning though: I’m pretty sure my 115-pound, 59-year-old frame could give you a run for your money.
***
Aaron Edward Olson is a multimedia journalist, award winning writer, and founder of MyReentry, a justice-tech platform placing powerful resources into the hands of citizens returning to the community. He is incarcerated in Washington State, serving a sentence of 51 years to life.
Deborah Zalesne is a Professor of Law at the City University of New York School of Law and author of Ending Isolation: The Case Against Solitary Confinement.
One Response
I read this earlier – and just reread it after talking with a pickleball-playing friend. I had heard of the game only recently. AND in the far past, my work involved supporting state-run college education courses in NYS prisons. This is a terrific interview – opening windows and shedding light upon lives and choices and relationships that I – at least – had never considered in this way. Thanks to Professor Zalesne and Mr. Olson for sharing their experiences – and to TheSportScribe for having the openness and imagination to publish their conversation, Now I’m going to read Professor Zalesne’s book, ENDING ISOLATION.