Little League® has taken JW O’Bryan places he and his daughter, Avery, could never have imagined. What started as something they watched together every August quickly became a goal they were determined to pursue.   

“It really boiled down to three years ago,” said O’Bryan. “We were watching these girls play softball on TV, and my daughter asked me, ‘How do I get there?’’ I told her that I didn’t know, only that we would have to have a pretty good team.”   

That question set O’Bryan on a journey to find an opportunity for his daughter to chase that dream. When he realized that there wasn’t a local Little League program supporting girls’ softball in their area, he and coach Jon Roberts helped create one.   

In their first year together, the team advanced all the way to the region championship in Whitestown, Indiana. A year later, with both O’Bryan’s and Robert’s daughters in their final year of eligibility, they accomplished their dream that started with a simple question. The gritty team from Owensboro, Kentucky, finally punched its ticket to the 2026 Little League Softball® World Series (LLSWS), Presented by DICK’S Sporting Goods, in Greenville, North Carolina.  

However, making it to Greenville was only the beginning. The girls put together an incredible run on softball’s biggest stage, winning the Purple Bracket Championship before falling just short to the girls from North Carolina in the LLSWS Championship game. Despite the loss, O’Bryan, his daughter, their team, and the entire community had an unforgettable experience.  

Recognized as the September 2026 Little League Diamond Leader of the Month, Little League sat down with O’Bryan for a Diamond Leader Discussion.    

“The Little League Diamond Leader program re-emphasizes what sports should be about for the people involved in running programs, coaching, and volunteering. For me, the training reinforced many of the things I already try to do as a coach, especially the importance of being a positive role model for these kids. It also gave me a greater perspective on the professionalism of Little League and the responsibility we have as representatives of the organization. Whether I’m representing Owensboro, Kentucky, or Little League as a whole, it’s important to understand how we should act, how we should treat people, and how we should treat our players and fans. The program makes you aware that when you’re in the spotlight, you are the face of Little League.” 

“The biggest lesson I’ll carry into future seasons is keeping the big picture in mind. We want to hold players, coaches, and parents accountable, but always in a respectful and positive way. If the kids feel comfortable, respected, and are having fun, they’re going to be able to handle adversity, play with poise, and enjoy the experience. That’s more important than wins, losses, or any individual performance.”  

“You have the opportunity to create lasting memories for kids and their families, but more importantly, you can help kids build confidence in themselves. Through this experience, our girls learned that if they set their minds to something, they can accomplish it. As a coach, being able to play a part in that is incredibly rewarding.” 

“Being a Diamond Leader means being a positive role model and understanding the impact you can have on a child’s life. Kids are like sponges, and the more positivity, respect, and role models we surround them with, the more we can help them grow into better people. As coaches, we have an opportunity to teach life lessons that will benefit them far beyond the field.” 

The Little League Diamond Leader program, which was first piloted with nearly 1,000 Little League volunteers throughout the 2022 season, was created as part of the Susan Crown Exchange’s Million Coaches Challenge and developed in coordination with the  Aspen Institute’s Project Play. Focused on ensuring children have a positive, well-rounded experience on and off the field, the Little League Diamond Leader Training Program is a FREE educational resource that provides coaches with an understanding of the impact that mental, social, and emotional well-being has in youth sports through detailed information, interactive scenarios, and a variety of additional resources. Learn more and become a Diamond Leader yourself by visiting LittleLeague.org/DiamondLeader.      

The Little League Challenger Division is proudly supported by Eggland’s Best, the Official Egg of Little League Baseball and Softball. An official sponsor since 2023, Eggland’s Best provides grant opportunities to local Challenger Division leagues each year and is the presenting sponsor of the Little League Challenger Division Exhibition Game at the Little League Baseball World Series each August.