Coach Chester – Lessons for Life and a Lifetime of Lessons

BY GINNY BENNETT PHOTO BY RAY WISHART

As a senior at Mosley High School when my friends and I began signing up for classes, taking Outdoor Education was almost a given. This is the class all seniors want to take, so of course I had to take it. As I walked into Outdoor Ed the first day of my senior year, I thought to myself, ‘Wow, this isn’t your average class.’ But now looking back, I see so much more than a unique course. I see Coach Chester and how lucky I was to have the best teacher in the world.

Winston Chester or “Coach Chester” has been teaching at A. Crawford Mosley High School for 40 years and has taught more than 11,000 students in his teaching career. He created his unique Outdoor Education program in 1993 and is proud that more than 80 percent of the seniors take this class as an elective. Coach Chester’s passion for teaching is rooted in relationships with his students. If you ask any student of his what they learned from Coach Chester’s class, it will far exceed the outdoors. Tales about Outdoor Ed will involve a lot of laughing and possibly tears. Coach Chester is much more than a teacher, to many he is a hero. He challenges his students not just to live ordinary lives, but extraordinary lives.

I remember every Monday walking into class and passing around the story stick. The story stick is pretty self-explanatory – you pass the stick around and every student is encouraged to share what he or she did that weekend and talk about something that involved the outdoors. In the beginning, this exercise didn’t mean that much to me but, looking back, I can see how Coach Chester cared about how we spent our weekends. He looked each student in the eyes and smiled his sweet smile and, no matter if your weekend was extraordinary or just ordinary, in that moment you felt extraordinary.

This hero’s story begins in the small town of Quincy, Florida in 1949. He grew up in what could be described as the typical American family. His dad went to work and mom stayed at home with Winston and his brother, Wayne. Coach Chester’s upbringing strongly influenced him to be the gentle person we all know today. “I was surrounded by love at a very young age,” he explains. His passion for the outdoors started when he accompanied his father on hunting trips and went camping with the family at a very young age.

He remembers those moments, looking up to his father, smiling and enjoying the outdoors and those early mornings when everyone else was asleep and he, his brother and father were out hunting. “The outdoors bonded us.”

Winston Chester remembers playing sports in the yard with his brother when they were young boys. He also remembers that his brother was always better than him. In middle school, Winston Chester started playing football and basketball on a team and discovered his passion for sports. He was much taller and bigger than other kids his age. It gave him an advantage and confidence in his physical abilities. He continued playing football and basketball in high school as well. One of Coach Chester’s biggest disappointments in life is his high school football team not winning the state championship after an undefeated record.

Only toward the end of my senior year did I hear through the grapevine that coach Chester played college football. So I went up and asked him about it in class one day. Without making eye contact he responded, “Now why are you asking that?”

“Well did you?” I replied. He avoided the question again and I pried and pried until he finally admitted he did. The humility he had in that moment stuck with me and is a quality I admire most in him.

As a senior in high school, Winston Chester was offered a football scholarship to the University of Florida. He remembers, “Now, this was a big deal, a small town boy, getting to play football at a big school. I took it.” Coach Chester says this opportunity was God’s hand and protection. He continued “During this time it was very common for young men to get drafted right out of high school to fuel the ground forces in
the Vietnam War. Now let me tell you, I would have been the first one to go. I would have been going as a Green Beret. I know I would have made the qualifications with my drive and my physical capabilities. Today I know the average time on ground for Green Beret military was two weeks. God was protecting me by providing this scholarship. I believe he wanted me to be here at Mosley and be able to invest in so many young people’s lives. If I had not gotten that scholarship, I believe I wouldn’t have been able to do what I do.”

He played defensive back at the University of Florida in his freshman year but sustained a concussion at practice in his sophomore summer and his physicians advised him not to play again. That marked his last year playing football, but he was able to stay at the University of Florida for the next three years on a scholarship.

During college, he married his lovely wife, Gail Gregory, and they have two children. Coach Chester graduated from the University of Florida with a bachelor’s degree in physical education and got his first job at Rutherford High School where he taught physical education for three years.

He has also earned a Master of Educational Administration from the University of West Florida and an Educational Specialist Degree from Florida State University.

Then he moved over to Mosley High School to teach physical education. In the 1980s he coached women’s track and basketball. He calls these former students “the ladies of the eighties.” Chester is very proud of this time in his career when he developed women’s sports at Mosley.

Coach Chester’s love for the outdoors inspired him to create his own class educating young people about the outdoors. He reflects, “My positive experiences in the outdoors at a young age made me want to share these experiences with my students.” His love for the outdoors came naturally as he began going camping with his family when he was still in diapers. He taught his first Outdoor Education class in 1993. It consisted of twelve boys. He nicknamed them “the dirty dozen.” The next semester two girls signed up in Outdoor Education and, once word got out, there was no going back. Amy Lamagdeleine, who was a student of Chester’s in 2008 says “He taught us Outdoor Education but he also would share life stories and lessons he learned from them. That’s not something teachers normally do.” He involved his students in outdoor projects, such as planting more than 20,000 sea oats along our beautiful beaches in Rick Seltzer Park and Mexico Beach.

Outdoor Ed is known as “The #1 Class in America” to any student in Outdoor Ed. Oh, and to everyone in America, of course. It was part of classroom etiquette that whichever student answered the classroom phone would introduce themselves saying something like “No. 1 class in America, this is Ginny!” It’s safe to say this class wasn’t ordinary.

Coach Chester is a man who wears many hats. Not only did he develop Outdoor Education at Mosley High School, but he wrote a book and produces his own daily television show. His wife helps him with the schedule for the Fox 28 TV show “Panhandle Outdoors with Winston Chester.” He admits he could never do what he does without her love and support. His two children are both teachers, following in his footsteps. His son, Chip Chester teaches Physical Education at Tyndall Elementary. His daughter, Wendy Woodrick, teaches U.S. History at Bay Haven Charter Academy.

His book is titled Full Box and is a reflection of Bay County’s local heritage of fishing, the  fishing industry, and boat building. This book is crafted from stories of older fishermen and was written out of Chester’s desire to “preserve historical stories.” Coach Chester interviewed either the person the story is about or those who remembered the original settlers. The entire process of writing and publishing the book took about three years. The hard work paid off. Today, 5,000 copies have been sold. He is hoping to have an area in the new history museum downtown for the history of fishing in Bay County and play the audio of these stories aloud.

With his outdoor television show, Panhandle Outdoors, he provides the latest information on what is biting, migrating, or moving and it is known for its famous Friday fishing report that provides a wealth of information for an avid outdoorsman.

Coach Chester still enjoys the outdoors by going scalloping and fishing with his family, two of his favorite things to do. As I chatted with him about my summer, he also shared with me his time in Cape San Blas with his family enjoying God’s beautiful creation. He has an annual reunion with high school friends at the tobacco farm he worked on when growing up, called Little Bit Farm. He enjoys the outdoors while catching up with old friends such as Tom Buttram, who he has been friends with for more than fifty years. Mr. Buttram describes Chester as a great friend, a man of character, of strong faith, and says, “Winston is a man who can be depended on.”

I like to compare Coach Chester to a tree. His roots are his faith and family, the tree is his teaching career, the branches are his book and television show, and the fruit of the tree are his students. Coach Chester has touched many lives through his teaching career. Next year will be his last year teaching and he plans to help people after he retires. He isn’t sure yet what that will look like, but I wouldn’t be surprised if it would involve touching even more than 11,000 lives.

I will always remember Coach Chester encouraging us in class to take time to help others in life. In class and on his daily television show, he can be often heard saying, “Do something good for your fellow man.”