For Stephen Cheskiewicz, being part of the Little League Challenger Division® is more than a role; it’s one of his most proud accomplishments. His passion for this program is personal. It began when Stephen and his partner adopted their son Michael when he was 14. At first, Michael was quiet, shy, and had a hard time making friends. Now at age 25, Michael has confidence, a community, and lifelong friends, all thanks to his involvement in Wyoming Valley Challenger Baseball Little League in Wilkes-Barre, Pennsylvania.
Eight years ago, the league had only 35 players, $700 in finances, and was given a field in poor condition in the city of Wilkes-Barre. Understanding the importance of having a strong, inclusive program for the athletes, the community and volunteers came together and built a facility that is not only ADA compliant but quickly became a new home for three Challenger Division teams for different age groups. Cheskiewicz has been there every step of the way and has seen firsthand how the program transforms lives, not just for his son, but for every child who steps on the field. From high-fives to playing walk-up music and celebrating every hit, Cheskiewicz has become an integral piece in helping players break barriers.
In 2025, the Wyoming Valley Challenger Baseball LL team had the opportunity to compete in the Little League Challenger Division Exhibition Game, Presented by Eggland’s Best, which is held at the Little League World Series in Williamsport each summer. It is hard for Cheskiewicz to put into words what that moment meant.
“The game at the World Series, I don’t think I have ever cried so much in my life. The kids in this division of play have behavioral, emotional, and motor issues,” said Cheskiewicz. “Whatever the case may be, seeing them all celebrated and making memories, it is a sight I can’t put into words, of how beautiful it is.”
Chekiewicz credited the Little League Diamond Leader Training program for helping him build his skillset when it comes to interacting with players, coaches, and volunteers within the Challenger Division.
“The Diamond Leader training emphasizes being player-centric, focusing on building kids’ self-esteem, emotional skills, balance, teamwork, endurance, and so much more,” said Cheskiewicz. “As I worked through the program, I realized that this training is not just for one group of coaches; it is for everyone, including the Challenger Division. It is an inclusive program that empowers coaches everywhere with the tools and mindset to lead the right way.”
Recognized as the September 2025 Little League Diamond Leader of the Month, Cheskiewicz shared his training experience in a Diamond Leader Discussion:
Why do you think it is important for coaches and volunteers in a Challenger Division to take the Little League Diamond Leader Training Program?
One word that sticks out to me most about this program is inclusion. This program showed me that our kids aren’t all that different from everyone else. The messages in the program apply to our athletes just as well as to somebody without a disability. As far as coaches and volunteers go, from an awareness perspective, these teachings are wonderful. We must understand our kids well, be patient, and work with their families to keep them safe. Understanding their disabilities and the lessons that this program provides helps us find ways to make our athletes better individuals on and off the field.
What lessons from the training do you plan to carry into future seasons?
The two lessons that I keep going back to are endurance and perseverance. I have watched this team grow, and the players individually grow. This whole perseverance thing really applies to our league. We started as just a small Challenger League, and we grew. We have all these Buddies now, we have all this community support, and within seven years, this little team turned into my greatest accomplishment. Not only have the kids persevered, but the volunteers have, the league has, the community has, and in that really short period of time, we have gone all the way to the Challenger Division Exhibition Game at the LLBWS, and the ride has been amazing.
What does it mean to you to be a Diamond Leader, and why should others strive to be the same?
It is so rewarding, with the Challenger Division players, to be part of something that is so much bigger than yourself. To see the kids smiling, having a good time, it is just something that I can’t even begin to describe. When you are with the kids in the Challenger Division and you watch them succeed while knowing that they are overcoming all these challenges, it is just magical to watch; it is so rewarding. To be a Diamond Leader and see all the other coaches, volunteers, and people involved with the team, pour their heart and soul into this, in my eyes, they are all Diamond Leaders, too.
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.