Kenny Osbeck

Some volunteers are easy to spot. They’re in the dugout, coaching third base, or celebrating with players after a big win. Others are working behind the scenes long before Opening Day ever arrives. For Kenny Osbeck, being a Game Changer means doing both.

Whether he’s creating hundreds of game schedules, coordinating field availability, coaching multiple teams, or simply being the loudest hype man in the dugout, Kenny’s passion for youth sports is unmistakable. His enthusiasm is contagious and his impact reaches far beyond the ball fields.

A West Michigan native, Kenny has been married to his wife, Jenny, for 13 years. Together they’re raising two children, Joey and Emma, who share their parents’ love of sports and adventure. The Osbeck family enjoys traveling, skiing, golfing, and spending as much time together as possible. “My wife, Jenny, is the rock of our family and keeps everything glued together,” Kenny said. “She will do anything for our kids and continues to support us day in and day out.”

Before joining Meijer, where he’s worked for the past eight years, Kenny spent five years as a high school math teacher. While his career changed, his passion for helping young people grow never did.

His journey with Caledonia Baseball & Softball League began four years ago after attending a public board meeting. “They asked for additional volunteers for the next season,” Kenny recalled. “I figured that if my family was going to benefit from this organization for the next several years, I ought to contribute.”

What started as volunteering quickly became much more. Behind every CBSL season is an enormous scheduling puzzle that most families never see. Kenny begins working on it each December with a massive Excel spreadsheet that evolves through hundreds of revisions before Opening Day. “It takes several hundred emails throughout the spring,” he explained. “Because several of our fields are shared with different schools, churches, and organizations. Coordinating everything is one enormous puzzle that I get to solve over several months.”

Fortunately for CBSL, Kenny admits that’s exactly the kind of challenge he loves. Beyond the spreadsheets, Kenny spends countless hours coaching, and that’s where his heart truly shines. “My favorite players are the ones who aren’t quite skilled at the game, but they give 110% every practice and game,” he said. “Watching them develop in character and skill is what I enjoy the most.”

His coaching philosophy is refreshingly simple. “I’ve been told I’m a ‘hype man,’” Kenny laughed. “Every play in baseball and softball has something to celebrate.” Whether it’s celebrating a player for swinging at a strike, hustling to first base after a ground ball, or recovering after an error...Kenny believes every moment presents an opportunity to encourage.

Inspired by Charles Swindoll’s poem Attitude, Kenny intentionally builds teams where positivity isn’t just encouraged, it’s expected. “I believe a team is only as good as they feel. Bringing energy and positivity drives practical results on the field.”

One of his favorite coaching memories perfectly captures that philosophy. During a playoff game this past season, one of his pitchers threw five incredible innings, allowing no hits and no runs while making several spectacular defensive plays. After the final out, something unexpected happened. “The other team ran to our dugout chanting ‘MVP’ and celebrated his performance,” Kenny said. “They were genuinely excited for him. It felt like something straight out of a movie.” Moments like those remind Kenny why youth sports matter.

While many recognize Kenny for everything he does, he’s quick to redirect the attention toward those around him. “The people I volunteer with are unbelievably inspiring,” he said. “Every coach and volunteer I’ve ever worked with motivates me to stay in the mix.” He also credits his family for making it all possible. “Having an incredible family that supports me is the only way. It takes a lot of planning and communication so we can honor all of our commitments.”

When asked what motivates him to continue volunteering, Kenny pointed to three things: the incredible people he serves alongside, using his God-given gifts for organization, and seeing the Cal-Plex filled with families enjoying youth sports. “The Cal-Plex is a beautiful image of our community coming together. I love that I get to schedule those moments.”

Receiving the CYSA Game Changer Award came as a complete surprise. “I was shocked because there are so many other people who deserve this recognition, especially on the CBSL board,” he said. “I certainly didn’t think I’d be the one receiving this.”

Like many volunteers, Kenny admits he often reflects on ways he could have done things better. “This award reminds me of the positive parts of my role and keeps me encouraged to keep pushing.”

Looking ahead, Kenny hopes CBSL continues building a culture where fun and competition thrive while negativity fades away. He’d also love to see the league reach 1,000 players in the coming years.

For anyone wondering what makes Kenny a true Game Changer, perhaps his own words say it best, “Love one another and ALWAYS find something to celebrate.”

Congratulations, Kenny, and thank you for the countless hours, positive spirit, and servant leadership you bring to CBSL and the entire CYSA community. You truly are a Game Changer!!

Sponsored by: Kristen & Nate Rounds