This week, we continue our spotlight on American Legion Baseball. Kurt Dusterberg interviewed Larry Bowles, who coached Chesapeake, Virginia Post 280 to the American Legion World Series in 2025.
Interview by Kurt Dusterberg
By the time Larry Bowles led Chesapeake, Virginia Post 280 to the American Legion World Series in 2025, he already knew the event was something special.
As a player, he had finished as runner-up for the Virginia state championship in 1994 and 1995—for the same team he was now coaching.
Bowles’ playing days were part of a different era, before youth sports became college-focused and ultra-competitive. So bringing a team to the American Legion national championship tournament represented a chance to do two things: win something special and, at the same time, tap into a baseball niche that represented simpler times.
Despite changes in the sport, Bowles has worked hard to preserve the spirit of Legion baseball. Here’s our conversation with him about his approach to the players and love of the game.
How have you seen youth baseball change in recent years?
Kids are trying to show off for college coaches in the eighth and ninth grade, and they have their personal trainers that they go to on a regular basis. They go to their pitching coach, and everything is hyper-focused on getting a scholarship. So, we tell them, “When you come play for us in the summer, our first order of business is, you have fun.” So we know we already have the camaraderie from the beginning; it’s just whether we have the talent or not.
You already had eighteen players who had college commitments to play baseball last year, so how did you approach last season?
We went into the summer telling the guys, “Look, you’re going to go play college baseball in the fall and it’s going to become a job.” So we sold them on: This summer, go out here, no stress, no pressure and just have fun. And sometimes it clicks. Last year, it really, really clicked. We had great team camaraderie on top of the team talent.
Do you put much emphasis on the association with the American Legion?
Before the season every year, we get them up to the Legion post to meet some Legionnaires. A lot of parents and players aren’t familiar with American Legion like they used to be. It’s important to understand that the guys who are fundraising for this are part of this organization. They are not just veterans, they’re combat veterans. They did things that most people in our country don’t want to do. When we see veterans, we thank them for their service. We even teach [the players] how to stand for the national anthem. But it’s not too much of a hard sell with our community. We have a very heavy military presence here in the Hampton Roads area [with Naval Station Norfolk.
Has it been difficult to keep the Legion program together as amateur baseball has changed?
In 2011, we had ten American Legion teams just in the Chesapeake, Norfolk, and Virginia Beach area. We had a whole league. By 2013, there were two teams. There were some years where we just could not put a team together. I think it was 2014 and 2015 that we didn’t have a team. I just fought tooth and nail to get a team back together in 2016. It was tough. I was barely putting some rosters together.
