The magic of the Cape Cod Baseball League follows all who choose to be a part of it. No matter how far these players, coaches, volunteers or interns stray from the Cape, all agree that one summer can change everything.

For Mr. Cape Cod himself, John Castleberry knows a thing or two about the magic of old Cape Cod.

At just 24 years old, Castleberry became the head coach for the then-Orleans Cardinals, now known simply as Orleans in his mind. This opportunity was a pivotal moment in his career. During his nine-year tenure as skipper, he gained the experience that set the stage for his future.

“I became the skipper for Orleans… It was an incredible experience that kick-started my career," he said. "Before that, I was at the University of Washington and grew up in Vancouver, Washington and Portland, Ore. I played junior college ball, then at the University of San Diego, and eventually coached at the University of Washington. That's how I began my journey in college coaching, and I never looked back,” reflected Castleberry.

As Castleberry explained, coaching in the northwest was becoming increasingly more and more limited, so he sought to turn back to the east coast where more jobs opened up.

Eventually, he ended up becoming the head baseball coach at George Washington in Washington, D.C., in 1984. Under his leadership, George Washington's baseball program flourished.

Over seven years, the Revolutionaries reached the Regionals five times, while Castleberry boasts a near-perfect graduation rate of 98%. Among his notable players was John Flaherty, who enjoyed a 13-year career in the Major Leagues with the Boston Red Sox. His pride in his former players is evident as he reflects on their success on and off the field.

“I'm very proud of all my guys," Castleberry said. "They're all doing great, they have great families and they're really good human beings. I like to say that a lot. They're good people.”

As much as Castleberry’s heart went into coaching, he began to notice a shift that took him in a different direction within the realm of baseball.

“So then in 1991, I decided to go into scouting and I thought, ‘You know what, I like developing people. But I'm going to try the scouting thing for five years and see what they come up with.’ And I've been in and now for 33 years. So I held on,” Castleberry noted on his transition.

Having been around baseball for nearly all his life, Castleberry knew a thing or two about the game. He started his new career with the Florida Marlins, being one of their first hires, and soon moved on to the Cincinnati Reds, serving primarily as an area scout. Following his time with the Reds, Castleberry then joined the Texas Rangers. An opportunity then arose with the Philadelphia Phillies as a cross-checker, where he then worked for four years.

Eventually, he joined the San Francisco Giants and has been with the Giants for 15, now going on 16 years, and adding to his already impressive baseball resume.

However, time and time again Cape Cod called back to Castleberry.

Having met his wife on Cape and even owning property in the town that jump-started everything, the dream of returning to the place that started it all lingered in his mind.

And so, when the opportunity to return presented itself, Castleberry jumped at it. But instead of returning to the dugout, it was as the 14th Commissioner of the Cape League.

When asked what this opportunity meant to him, he took a moment to reflect, and with a smile, he said:

“I always kind of wanted to do this. It's a full-time deal to become the commissioner of the Cape Cod Baseball League… I think I bring the avenue of professional sports and what the scouts and pro-ball people need and want when they come to visit the Cape and evaluate the players. But at the same, time I've learned a lot so far.”

What ensured a smooth transition into the role was a strong understanding of the magic that the Cape League provides to players, fans and the legion of volunteers whose support drives the league.

“Everybody looks back and agrees that summer on Cape was the best summer they’ve ever had… That’s one of the things that was instilled in me when I came in, our goal is to make sure our players have the same great experience as the rest of us.”

With the 2024 season within arms reach, the field is set for Castleberry, and all eyes in the baseball community are fixed on the former skipper as he embraces this fresh opportunity to lead the next generation of the Cape Leaguers to greater heights.