Roger BelAir
Roger began his second career in 2017, entering Chicago’s Cook County Jail to teach pickleball to men awaiting trial. He believed the game could build cooperation, communication, and emotional regulation—skills essential for re-entry. With most inmates eventually returning to their communities, he hoped pickleball could ease tensions inside and help create safer neighborhoods. That leap changed many lives, including his own.
Before this work, Roger had a long career in banking and real estate. He jokes that he’s now “been in more prisons than Al Capone.” His understanding of pickleball is unusually deep: he befriended Barney McCallum, the sport’s last living founder, and learned directly from him and the Pickle-Ball, Inc. team. This foundation shapes his clinics, known for humor, insight, and solid technique. He has taught more than 4,000 people—from Wimbledon pros to executives to grandparents—and is a frequent Guest Teaching Pro at Rancho La Puerta.
His first jail program was a breakthrough. Men charged with murder, many from rival gangs, soon played together, communicated, and eventually laughed side-by-side. Disciplinary issues fell.
““There are people who come from the perspective that there shouldn’t be fun or games in prison and say that they are there to be punished. I understand both sides, but even if you don’t want them to have joy, if you could cut use-of-force incidents in half, isn’t that better for everyone?” ”
Pickleball clearly worked. What began as one class became a national movement: since 2017, Roger has introduced pickleball to 24 prisons in 7 states, co-founded PICLeague.org to help others replicate his model, and inspired programs now running in more than 40 facilities in 10 states. His work has been featured by major media outlets, and a documentary, Pickleball in Prison, is in production.
Roger now focuses on recruiting and mentoring volunteers nationwide, teaching them not only the sport but how to build trust, show empathy, and model respect—key to scaling the program sustainably. With nearly 4,000 facilities in the U.S., the need remains immense, and he is committed to expanding the movement.
Off the court, Roger is a respected financial expert, bestselling author, and national keynote speaker, quoted in The Wall Street Journal, The New York Times, and more. And at 79, he continues his mission with the same passion: finance may be his background, but pickleball is his calling.
