Winter Garden Squeeze's new coaching staff combines college coaching and MLB experience

Every summer, the Winter Garden Squeeze welcomes a new roster, but this season also brought a new coaching staff. 

Head coach Steven Crabtree and assistant/pitching coach Dewon Brazelton stepped into their purple and orange gear to guide the collegiate players. 

Although they came to the Squeeze from different worlds — Crabtree with his background in collegiate coaching and recruitment, and Brazelton as a MLB first-round pick and Team USA athlete — the combination of their unique perspectives has become the foundation of the team’s summer campaign.

COLLEGE PROSPECT TO MLB

Before Brazelton was helping Squeeze pitchers in summer baseball, he was one of the country’s best young arms. He grew up in Tullahoma, Tennessee, surrounded by athletes and constantly walking around with a ball in hand. 

He was a star player for Tullahoma High School before earning a full scholarship to Middle Tennessee State University. 

In college, Brazelton quickly found himself as one of the nation’s top pitchers. After his freshman season, he was invited to play in the Cape Cod League, similar to the Squeeze’s summer baseball league. Then a year later, he earned a spot on Team USA.

“When I was at MTSU, I was doing really (well), but I just thought I was doing (well) for somebody local,” he said. “I didn’t realize what I was doing and how good it was, but once I got inducted into the (MTSU) Hall of Fame (2013), I was able to look back upon the time and feel better about myself after other people recognized it.” 

Brazelton saw his hard work in training pay off in 2001, when he was chosen as the third overall pick by the Tampa Bay Devil Rays in the MLB draft. He enjoyed a five-year career in the major leagues, traveling and being paid to play the game he loved. 

But the most significant result of his professional career was the foundation it laid for his current role as a pitching coach for his academy Dewon Brazelton Pitching Academy in Winter Garden. 

It started with one player asking Brazelton to help him, then another and another — until he had 15 kids pitching in a park. Today, more than 100 players train at the academy. 

“I really feel like I was born to do this,” he said. “I think playing in the big leagues is a big part of it. I played there, and that gave me instant credibility with the kids. And so now I’m able to talk to them and teach them how to do certain things, and I mentor them about their grades, about every aspect of life.” 

For his Squeeze partner, Crabtree, teaching and developing players is what made him realize his desire to be a coach. 

CAREER IN COACHING

In high school, Crabtree loved the camaraderie with players and the relationships built over time. He could see how big of a role coaches had on players’ development —not only as a athlete but also a person — and knew he wanted to hold that role one day.

“There’s a greater purpose to it,” he said. “You’re using these lessons that you’re using in coaching a game to hopefully translate that to life and how you’re going to come through adversity when things happen in your everyday life.” 

Crabtree’s baseball journey as a player ended in his freshman fall semester of college. He had to chose between working full-time or playing. He decided to take a job — even though his love for baseball hadn’t faltered. 

After five-and-one-half years away from the sport, besides men’s leagues across Orlando, Crabtree made his return to the field in 2006 by assisting with Olympia High’s JV team. 

“It felt great to get back into it,” he said. “I had to walk away from playing it, and it helped me to really dive in and do everything I could to help with players and help them understand you never know when the last practice or the last game is going to happen so don’t take each day for granted.” 

The step launched his coaching career. 

Crabtree worked at many levels of baseball, including stops at Nyack College, Rollins College, Weber International and Florida Southern College. He even coached two years in the Florida Collegiate League in 2013 and 2014 as an assistant on Orlando Freedom and College Park Freedom. 

The eight years at Florida Southern as a recruiting coordinator and associate head coach for two of the years under Lance Niekra taught Crabtree his biggest lesson to players: “Don’t change who you are.” 

“Being you is going to be who makes you the most confident and feel the best,” he said. “I don’t want to change too much of who I am, and I don’t want them to change too much of who they are, because again, that’s when we’re all going to be at our best.” 

It’s exactly what he’s emphasizing to this summer’s Squeeze roster. 

“It’s been an honor and a privilege, and this is an experience that I obviously have wanted for a very long time,” Crabtree said. “I took over Trinity Prep in January this year as a head coach, so this is my second, third-ish experience with running the thing, and it’s been phenomenal. Those people (who) believe in you and trust you: Those are the ones (who) always hold an extremely special place in my heart, and I’m forever grateful.” 

SQUEEZING IN 

Finding their way to the Squeeze this summer all became possible through General Manager Adam Bates. 

Crabtree met Bates years ago through the baseball community in Florida, and the job offer instantly piqued his interest. He had been looking to get back into coaching college players. 

“It’s really fun to coach college players because of the baseball IQ, being able to work and dive into things with them and really push them to big limits and everything else,” Crabtree said. “As I tell those players all the time. ‘The difference between a professional athlete and them is all mental.’”

For Brazelton, the pathway became available through his pitching academy. He has athletes across Orlando-area high schools, and a mutual friend connected him with Bates. But Brazelton was hesitant at first: Did he want to commit to the travel with coaching?

In the end, he snagged the unique opportunity to work with players who are older than the average at his academy. 

“I try to breathe life into them,” he said. “Right before we go out there (for a game), I talk to them about making sure they know they’re good enough. They’re good enough at what they’re doing. … If you talk to anybody about my personality, I’m super positive. I don’t believe that you tear a kid down or a player down.” 

When the Squeeze opened its summer practice, Crabtree and Brazelton were strangers. 

Within the first month, their dynamic has blossomed.

“Coach Crabtree is what I would call a baseball man,” Brazelton said. “He loves everything baseball. He loves fixing grass. He loves lining the field. He loves making sure everything is right.”

Crabtree takes the hands-on coaching approach. He enjoys every aspect of running a program, from preparing the field to tackling the game strategy. Brazelton focuses on developing pitchers and mentoring them through the mental side of the game by utilizing his MLB experience. 

“We were in the middle of a game the other night and I looked at (Brazelton) and I was like, ‘You got so much more knowledge about this game than me, so I’m all ears when you talk,’” Crabtree said. “I always love to surround myself with people that know more than me because I just feel like that’s how you learn.”