Winter Park High School community remembers Derek Gwinn

He was larger than life — yet life was never about him.

The Winter Park High School community is mourning the loss of a loving father, son, mentor, friend and graduate in Derek Gwinn, who died suddenly April 3. He was 58. 

Gwen was born in Spartanburg, South Carolina, and his family moved in 1972 to Winter Park. As a student at Winter Park High, Gwinn enjoyed great success on the football field as an offensive and defensive lineman, moving on after graduation in 1979 to compete on the gridiron for Georgia Tech.

His play got him noticed at the NFL level, and Gwinn enjoyed a two-year stint with the Kansas City Chiefs.

For years after his graduation, Gwinn felt the calling in his heart to support his high school, joining the Winter Park High School Foundation to support and fundraise various projects and improvements.

The foundation’s Director of Charitable Giving Vince Furey was a close friend of Gwinn for the past seven years.

“He loved Winter Park High School, loved Winter Park High School football, loved the community of Winter Park, and he was just one of these guys that had this big personality,” Furey said. “Somebody at his funeral said the energy of a room changed when he walked into it. That’s an absolute fact. He just had this personality that would pick you up and make you feel bigger than you are.

“If we had some need (at the foundation), he would help network and help facilitate an opportunity to meet that need, whether that was him personally or other contacts he had in the community,” he said. “He was definitely a doer. … It didn’t have to be just the football team, it could be anything really related to the high school. … There was never a ‘no’ from Derek.”

Some of the projects Gwinn helped support included the re-painting and renovation of the school’s athletic center weight room and main hallway, as well as the purchase of the signature inflatable Willie the Wildcat tunnel the football team runs through at home games.

But Gwinn was more than just projects and fundraising. Beyond his first priority — which was always pouring into his daughter, Jordan Alexis, and son, Jack Henry — Gwinn also took many Winter Park student-athletes under his wing.

“He was a guy who was really mentoring kids on the team,” Furey said. “He wasn’t just showing up and watching; he was actually working with kids and players. It’s something that he loved to do. There was a bunch of kids (who) were really positively impacted by the time he took personally to spend with them.

“Certainly, a lot of it revolved around football, because he was an offensive lineman too,” he said. “But I think part of it is also just becoming a man, balancing athletics and academics and being the right person. Derek seemed like he never had a down day. He was always up, always positive and always boosted up your spirits when you were around him.”

It was an incredible thing to witness for former Winter Park High School football defensive coordinator Charles Friedley, who coached Gwinn on the football field and also taught his 10th-grade biology class.

Friedley remembers how well Gwinn balanced athletics and academics — a key factor that got him into Georgia Tech.

It was special to watch Gwinn mentor students pursuing their own success, Friedley said.

“As far as being a person that accomplished a lot, he wanted to give it back,” he said. “He wanted to give it back to his community and his school. That was his endeavor.”

Winter Park High School assistant football coach Johnny Miller saw much of that mentoring firsthand, as well. He grew up with Gwinn and witnessed him grow as both a football player and a person.

“He was a kid that went to Winter Park and got a lot out of Winter Park — it was his high school, and he gave back,” Miller said. “It’s refreshing to see people (who) are willing to do that.”

Winter Park High graduate Neal Hayes met Gwinn during his years as a Wildcat on the track and field team — Hayes was a runner and Gwinn threw the shot put and discus. They both graduated in the class of 1979 and were close friends until Gwinn’s passing, Hayes said. 

Gwinn was easy to spot in a crowd because of his large football frame — standing at about 6-foot-5 and 250 pounds — but the size of the man’s heart far exceeded his stature.

“He was larger than life — both literally and figuratively,” Hayes said. “He was great at reaching out to people and always tried to help out people any way he could. He wasn’t good at receiving help. He was like, ‘What can I do for you?’ more than what you could do for him.”

Gwinn is survived by his daughter, Jordan Alexis; son, Jack Henry; father, William B. Gwinn; brother, W. Bradford Gwinn, Jr.; sister-in-law, Cheri; nephew, Justin; niece, Kelsey; and his “lady love,” Sheryl King.