Standing on the South Sumter High School football field, Keith Hileman let the memories wash over him. The roar of the crowd, the dedication of the players and the countless moments that defined more than three decades of service filled his mind. 

“A lot of history happened here,” Hileman says. “But what makes me most grateful is seeing all the kids who graduated from here coming back to serve the community. That’s what it’s all about.”

After 35 years as a coach, teacher and mentor, Hileman is retiring, leaving behind a legacy that has shaped generations in Bushnell. His impact extends far beyond the field or the weight room—it’s etched into the culture and traditions of South Sumter High School.

A Career Born of Opportunity

Hileman’s career in education began in 1990 after he and his wife Debbie moved to Bushnell from the Midwest. The couple had taken a chance on Florida after Hileman left a feed mill job in Nebraska. 

“My wife was teaching in Nebraska, and I was working in the mill,” Hileman explains. “We decided to take a shot at coming to Florida. A week before school started, I got a call from Inman Sherman, the athletic director, and Bob Edwards, the principal at the time. They needed a teacher and a coach. I got lucky. I was ready to go on unemployment, but instead, I ended up at South Sumter.”

What started as a hopeful leap turned into a career filled with purpose. Hileman began coaching football in 1991 and later expanded to basketball, track and field, and even softball. 

“I’ve been coaching football for 35 years, basketball for 26 years, and I spent about 10 years with track and a few with softball,” he says. “For the last eight years, I’ve also been the athletic director and took over after Inman Sherman retired.” 

Throughout his career, Hileman has seen South Sumter grow and change, but one thing has remained constant—the strength of its community. 

“South Sumter is unique in that people stay,” he says. “Our administration, teachers, and coaches are dedicated to this place. It’s not like other schools where there’s a lot of turnover. People spend generations here, and that’s special.”

The school’s motto, “Tradition Never Graduates,” holds a deep meaning for Hileman. 

“The coolest thing is seeing former students come back,” he says. “We’ve had Clinton Hart and Keanu Neal have extensive careers in the NFL. A.J. Bryant played here and is now the varsity basketball coach. They all gravitate back to South Sumter and the area because this place is home. It’s something that keeps the legacy alive.”

Hileman has also been a part of the school’s evolution. For 33 years, he personally painted the lines on the football field, a labor of love that took hours in the blazing Florida sun. 

“Every line, every marker—I painted them by hand,” he recalls with a chuckle. “They were going to get a Turf Tank robot to do it a few years back, but the county decided to invest in a turf field instead. It’s been great for the kids, and I don’t miss all that time out there in the heat!”

While the new facilities are a welcome change, the bonds he’s built with students and colleagues mean the most. 

“Coaching is a special thing,” he says. “It creates a bond that brings people together. You feel like you’re part of something bigger.”

The Influence of Mentorship

Hileman credits much of his success to the guidance of Sherman, the legendary South Sumter football coach and athletic director who gave him his first opportunity.

“Sherman is the reason I stayed here so long,” Hileman says. “When I was young, I told him, ‘Whatever you want me to coach, tell me how to do it, and I’ll coach it that way.’ That trust meant everything. Over the years, we had our disagreements, but we always worked through them. After a tough day, we’d go out for dinner and talk it over. That bond kept us going.”

Even after Sherman’s retirement in 2016, Hileman carried on the same philosophy, building trust and developing young athletes.

“When coach Ty Lawrence took over from Sherman, we took those same concepts and built on them,” Hileman says. “We know what to look for in kids, and that’s helped us grow. This year, we had five kids commit to NCAA Division I programs. That’s a testament to the hard work everyone puts in.”

A Legacy of Impact

Hileman’s influence isn’t limited to athletics. Over the years, he’s taught countless students, instilling the same values of discipline, hard work and respect.

“We’ve had Harvard lawyers, veterinarians, scientists, you name it,” he says. “You get out of education what you put into it, and South Sumter offers kids the opportunity to succeed. The community here makes that possible.”

As Hileman prepares to retire, he’s taking time to reflect on the people who made his journey possible, starting with his wife, Debbie.

“She’s the backbone of our family,” Hileman says. “She stuck with me through all the long hours and raised our kids while I was coaching. She has supported me every step of the way. We’re looking forward to spending more time together and seeing what’s next.”

While retirement will bring a new chapter for Hileman, his love for South Sumter High School will never fade.

“I’ve had the best job in the world,” he says. “Coaching, teaching, and building bonds—it doesn’t get better than that. But it’s time. I’m ready to retire and see what life holds outside of the classroom and the field.”

As he prepares to step away, Hileman remains confident in South Sumter’s future.

“The school has a fine future ahead,” he says. “The kids and administration here are special, and the community makes it all work. I feel lucky to have been a part of it.”

Photos: Matthew Gaulin