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Max O'Leary

Max O'Leary

Max’s pickleball journey began when life brought him back home to Cincinnati. Fresh off the West Coast in the spring of 2023, he dusted off a paddle set he’d been gifted for his birthday and headed to Sawyer Point—where one game was all it took. He was instantly hooked by the fast pace, the continual improvement, and the friendships that came with every match. Nearly three years later, that same mix of challenge and community still drives his love for the sport.

As a PPR- and DUPR-certified instructor, Max blends competitive experience with a calm, analytical teaching style. He’s earned Gold in Men’s 4.5 at Dink Cincy, Silver in Mixed 4.5, competed at the 5.0 level at the WPT Championships in Macon, and continues to build success with each tournament. Before he ever taught pickleball, Max honed his instructional skills teaching Hebrew to 4th graders and tutoring students at Kilgour Elementary—experience that shines through in his patient, thoughtful coaching.

Max loves working with players of all ages and skill levels, but especially enjoys helping athletes master the drop shot—one of the most transformative skills in the game. Players can expect a balanced approach that blends strategic insight with encouragement. His goal is to quiet the perfectionist mindset many players bring to the court and replace it with confidence, clarity, and purposeful growth.

For Max, pickleball is both a physical and mental outlet—an engaging space where the pursuit of improvement never ends. The sport has brought him some of his closest friendships and has been, in his words, “quite possibly the single best thing for both my physical and mental health.” One of his favorite memories comes from a team tournament in Cleveland: after renting a car, waking up early, and driving more than four hours to compete, his team lost every match—but laughed the entire way home, making the return drive the highlight of the trip.

When he’s not drilling, competing, or vibing to his go-to hype song (“Pink Pony Club”), Max might surprise you with one of his lesser-known talents—he can wiggle his ears. His pickleball idol is Zane Navratil, a pioneer of the sport known for both his skill and innovation, qualities Max deeply admires.

Max is a certified instructor with the Ohio Pickleball Academy at The Pickle Lodge, where he brings positivity, perspective, and a love of continuous improvement to every session. Ready to train with Max? Click here to book a lesson and click here to view our upcoming clinics.