Koss family sharing special summer working with Winter Garden Squeeze

Growing up in the suburbs of Detroit, the game of baseball was passed down to Brian Koss like a family heirloom. Whether it was his grandfather telling tales of rooting on the Honus Wagner-coached Pittsburgh Pirates in the 1930s or his dad making sure the family’s annual summer vacation always included a detour to an MLB stadium, baseball was stitched into the fabric of Koss’ life from the very start.

As the years passed, Koss’ love for the game continued to grow. Because of these experiences, a love for the game’s history and an educational path that helped him develop his skill with the written word, he decided take his passion for America’s pastime and do something more.

“Throughout undergrad and graduate school, I had to write a lot, so I always liked writing and researching, and I’ve always loved baseball, so I had just a ton of baseball knowledge and interest that I thought to myself I should do something with it,” he said. “I always felt, too, that I left baseball too early and that I could have kept being involved in the game beyond playing in high school and following it as a fan in college and as a young adult. I felt like I could have done more in the game, maybe as a player, but more so maybe I could have taken a different career track and gone on to work in baseball.”

That thought motivated Koss to get back into baseball in a real way. These days, he has been putting his knowledge of the game to good use as the co-owner, managing editor and podcast host for Legends on Deck — a one-stop shop for youth, collegiate and professional baseball content.

“At the time I started writing, I was in my early 30s,” he said. “I thought to myself that anybody who has a knack for writing can become a writer at any point given how media and technology has changed in recent years. … That’s kind of when I (dived) in on the idea of becoming a baseball writer and decided to make a go of this and start building something.”

Koss did exactly that. However, after almost a decade since this deep dive into the world of baseball began, he’s gotten the chance to do something beyond his expectations: Spend this summer sharing his passion for baseball with his four children, passing down the love of the game just as his father and grandfather did for him. 

Squeeze squad

Through relationships Koss built because of his work with Legends on Deck, he connected with Adam Bates, general manager of the Winter Garden Squeeze.

“Since launching the podcast, I’ve had the chance to connect with a lot of different baseball people, and one of them was Adam,” Koss said. “Back in 2022, he was running a youth camp with Johnny Damon and the Squeeze at Veterans Park in Winter Garden, and I brought my son, George, who was only like 6 at the time. We connected at the camp, and I showed him all the work I was doing. We just hit it off and became friends, always talking baseball and sharing different ideas we had for each other. Then the next season, George became the batboy for the Squeeze, and since I was there every game with him, I’d write about the team.”

For the next two summers the Koss boys — George as a batboy and Brian as the Squeeze’s unofficial beat reporter — became more than family to the team’s coaches, players and staff. They became members of the Squeeze Squad, which is why it was a no-brainer for Bates to figure out who his first call would be to fill his vacant assistant general manager role.

“Fast-forward a little bit to this season and we find out … the Squeeze are going to play their games at Horizon High,” Koss said. “I was particularly enthused because I live across the street. After not being able to go to all the games last summer, the move was great, because I knew I could take George to every game and keep writing about the team. That’s when Adam asked me to join the staff as his assistant GM. He was like, ‘Well, you’re entrenched over here, and because you know the area so well you could really help us grow our presence with a newish audience.’”

“It was a no-brainer,” Bates said. “He’s locked into to the team and the area, and having his son, batboy George as member of the family already just made it an obvious fit. He’s a great baseball guy, a very talented writer with a great platform in Legends on Deck. And since the summer of 2023, we’ve done a lot together and become close so it was just a natural fit. When we moved out to Horizon, he was my first ask.” 

When this opportunity presented itself to Koss, the benefits of it were obvious: Spend the summer with his son surrounded by not only the sport he loves but also a team that has become family. What wasn’t obvious to the father of four was that this new role would mean his three daughters would soon become the newest members of the Squeeze Squad. 

Photo by 347689101921254

“Obviously, George has been into baseball pretty much his whole life but my oldest, Providence, is not a super sports enthusiast,” Koss said. “But because she’s going into high school next year, she was looking for opportunities to volunteer, and this was a perfect place for her to do that. … And because there’s a lot of concourse space that’s also fenced in at Horizon it creates a nice area for kids to play, so my youngest two daughters have been able to enjoy the environment a lot, as well.”

Just as any parent with multiple children can imagine, finding an activity that satisfies all of the kids is nearly impossible, which is probably why Koss is so grateful to not only see them all enjoy themselves in the same place but also to do so at baseball games for an entire summer.

“I’m really lucky to be having this experience with my kids this summer,” Koss said. “Seeing my little ones out there having a great time playing with other kids and being part of the atmosphere is awesome. Having George not just be a batboy but also help out with his sister at the ticket stand or at concession has been fun. And even though Providence isn’t the biggest baseball fan, it’s been amazing to see her take on the responsibility and really enjoy the social atmosphere at games. We’ve definitely made games a family event that they really like to be part of, so I’m happy about that. Seeing all of them interested in spending time up there and being a part of this team. It’s been a fun experience to have everybody around and to be excited about going.”

For George, although he will forever be known in Squeeze history as ‘Batboy George’, he’s enjoyed the opportunity to help in different ways this season.

“It’s been so much fun to be a part of the Squeeze these past three seasons,” George Koss said. “This year, I’ve been able to help in different ways, too. Sometimes as bat boy, sometimes I take tickets with my sister. I really enjoy doing the raffle — walking around with the players and selling raffle tickets to fans. I just love being at the ballpark with the team, the interns, friends that come to the games and my sisters, too.”

As for the oldest Koss kid, learning new skills while working alongside the Squeeze Squad has been great a way to spend the summer.

“I’ve really enjoyed my experience working along side my dad, brother, Adam and the interns this summer,” Providence Koss said. “It’s been a great opportunity to learn how the games function. I’ve never been a big baseball fan, but these are really fun social outings and I’m learning new skills and responsibilities. I particularly like that the games are at Horizon, where I’m starting as a freshman in August.”