Diane Simon, NBA Cookie Mom: Most Interesting People 2026

Why She’s Interesting: For almost five decades, Diane Simon has been a fixture at Cavaliers games, greeting players with bags of her homemade cookies. She’s baked for dozens of players, from Michael Jordan to LeBron James. 

How It Started: Simon’s cookie legacy began when she babysat for Cavaliers players Jim Brewer and Jim Chones. When former Bulls player Jim Cleamons offered her tickets to a game, she decided to thank him the best way she knew how — with homemade cookies for him and his wife. Soon after, she was baking for Jordan, Scottie Pippen and players across the league. 

The Sweet Spot: Simon bakes about 10 dozen chocolate chip, oatmeal raisin, peanut butter and sugar cookies per game, packaging five or six in each bag for players to grab after the final buzzer.  

Beyond the Cookies: Before she became known as the NBA’s Cookie Mom, Simon spent more than 40 years working outdoors in utility and communications for the Illuminating Company and AT&T. After retiring, a conversation with her parish priest led her to Holy Name Elementary, where she now works part-time as a teacher’s aide. “This is my third year. I love the kids.” 

Still a Fan Favorite: Simon continues to attend Cavs home games and even travels to cities like Detroit, Chicago and Washington D.C., cookies in tow. “Some players say I’m the best reason to come to Cleveland. When they come out of the locker room, waving and yelling ‘Cookie Mama,’ it makes my heart feel good.” 

Meet the rest of the 2026 class of Most Interesting People >>

For more updates about Cleveland, sign up for our Cleveland Magazine Daily newsletter, delivered to your inbox six times a week.

Cleveland Magazine is also available in print, publishing 12 times a year with immersive features, helpful guides and beautiful photography and design.