Roger BelAir has been to prison many times, all for pickleball.

BelAir (’69 Busi.) loves pickleball because it brings people together. He first played the sport about 10 years ago and fell head over heels for it. As he shifted toward retirement, he began coaching at clubs and rec centers where he helped others get hooked on the game.

A self-proclaimed Pickleball Evangelist, BelAir’s reasons for singing pickleball’s praises are many: It’s great exercise. It’s easy to learn, not too strenuous on the joints, and you can excel at it no matter what your age or build. Best of all, there’s a camaraderie and friendly competitiveness around pickleball that make you forget your worries and focus on fun.

Pickleball is “the fastest growing sport in America” (The Economist, 2021) with over 4 million Americans saying they play at least once a year. And Senate Bill 5615 made pickleball the official sport of Washington state in 2022!

These benefits of pickleball were top of mind for BelAir in 2017 when he tuned into a segment on 60 Minutes. The reporters were covering Cook County Jail in Chicago and its enormous struggles with overcrowding, violence, and mental health issues. The solution was obvious to BelAir. “These guys are just sitting around,” Roger pleaded to his wife and the TV set. “They should be getting off their butts, playing pickleball, and learning life lessons.”

BelAir promptly wrote to Cook County Sheriff Tom Dart and offered to donate equipment and coach inmates for free. Three months later, BelAir was standing on a pickleball court inside the third biggest prison in the United States surrounded by intimidating glares and abundant tattoos.

Roger BelAir with his pickleball converts at Cook County Jail
Roger BelAir with his pickleball converts at Cook County Jail in Chicago (Courtesy Roger Belair)

“It was a rough start,” BelAir recalls. “My lecture on pickleball’s origins wasn’t going over well. So, I cut off my speech and said, ‘Let’s head out to the courts.’” All it took was five minutes and the inmates reverted to their 12-year-old selves, hitting plastic balls over nets and laughing like kids on a playground.

It was clear to BelAir that he was on to something.

BelAir continued his lessons at Cook County Jail, using humor and boundaries to keep the fun and integrity of the game intact. “In prison, there are gang leaders that make the rules for everybody,” he explains. “Sometimes these ‘shot callers’ would decide to change the rules of pickleball, and I wouldn’t let them.”

It didn’t take much to keep his players in line. The inmates knew that participation in the game was a privilege that could be revoked. An hour on the pickleball court was a bright spot in a tedious existence. No one wanted to risk losing it. This leverage, paired with BelAir’s jovial approach, allowed him to earn the inmates’ trust and accomplish some amazing feats⁠—like getting rival gang members to be doubles partners.

BelAir’s stint at Cook County ended up being hugely beneficial. Pickleball gave these competitive, highly charged inmates a calm, healthy outlet for their stress. The game was less physical than basketball, which meant fewer fights and injuries and broader participation. BelAir’s coaching helped foster unlikely friendships and encouraged teamwork, respect, and rule-following.

As word of his success at Cook County spread, more prison administrators sought out BelAir’s services. Soon he was introducing pickleball in prisons from Rikers Island in New York to the Washington State Penitentiary in Walla Walla. He was on his way to California’s San Quentin State Prison in 2020 when COVID-19 hit and sent BelAir, and the rest of the world, into a holding pattern. He found himself stuck on the outside while inmates inside faced extreme isolation and would have given much for a carefree hour of pickleball and laughter.

Fortunately, BelAir doesn’t give up. As soon as he’s allowed, you can bet he’s going back to prison to share his love of pickleball.

Web extra

A concise history of pickleball

On the web

What is pickleball? (USA Pickleball)

Video: How a man’s love for pickleball led him to coach prison inmates across the country (King 5, October 28, 2019)

Pickleball Is Ready for Prime Time (The New York Times, February 18, 2022)

A Pickleball Court: The Hot New Amenity in Real Estate Developments Today (Architectural Digest, March 2, 2022)