Dale Leon Phelps, age 91, of Leesburg, Florida, passed away peacefully on March 13, 2025, surrounded by his loving family. He was born on July 9, 1933, in Otter Creek, Florida, to the late Grady and Thelma Phelps.
Growing up, Dale worked in his family’s store from a young age, where he fondly recalled the pulpwood workers who would come in early each morning to purchase a Pepsi and a Moon Pie. As a teenager, Dale also worked as a pulpwood worker, and he often shared many wonderful memories of those hard-working days. These early experiences instilled in him a strong work ethic and a deep connection to the community.
Dale graduated from Bronson High School at the young age of 16. He then attended the University of Florida before graduating from Massey Business College in Jacksonville, FL. Following his education, Dale proudly served his country in the U.S. Army from 1953 to 1955, stationed at Fort Monroe in Hampton, Virginia.
After his service, Dale worked for the Florida Game Commissioner alongside his brothers. This period of his life was particularly fulfilling, as it allowed him to blend his deep appreciation for nature with his strong sense of family. Dale cherished these years, and he often regaled his family and friends’ colorful stories of his many adventures in the field. Whether it was recounting his experiences tracking wildlife or his fondness for working alongside his brothers, those stories reflected his love for the outdoors and the strong bonds that he shared with his family.
Dale later enjoyed a successful career as a Metro Manager in Circulation for the Orlando Sentinel, where he was known for his dedication and leadership. After retiring in 1990, Dale and his beloved wife, Geraldine “Jeannie” Georgia Shockley Phelps, settled in Leesburg, Florida, where they enjoyed their golden years together.
Dale and Jeannie shared a beautiful marriage, which began on October 4, 1958. Their love and devotion to one another lasted for 66 years. Dale’s family was his greatest joy, and he took immense pride in being a devoted husband, father, grandfather, and great-grandfather. His love for his family was immeasurable, and he stood behind them no matter what. He will be remembered for his kindness, his unwavering faith in the Lord, love for others, and the warmth he brought to all who knew him.
Dale had a special love for fishing, particularly on the Gulf of Mexico (America). It was one of his greatest pleasures, and he found peace and joy in the water, surrounded by the beauty of nature. His passion for fishing was not limited to the Gulf; he also enjoyed feeding the fish in the creek in the backyard, ensuring that his grandsons and great-grandchildren could always catch a fish. He instilled his love for fishing in all of them, creating memories that will last for generations.
Daddy also had a great love for reading. Robert W. Service was one of his favorite authors, and he would often read “The Cremation of Sam McGee” to us, as well as many other wonderful short stories. His love for literature and storytelling left a lasting impact on all of us and brought us closer together as a family.
He was preceded in death by his daughter, Karen J. Wells; his parents, Grady and Thelma Phelps; and his brothers, Darwyn and Joseph Phelps.
Dale is survived by his loving wife, Jeannie; his brothers: Grady W. Phelps and Gary (Bunny) Phelps and sister, Susie (Sammy) Long. His children, Kelly (David) Wells, Kandi (Will) Maynard, and son-in-law Bobby Wells. He is also survived by his cherished grandchildren, Robert “Chase” (Jessica) Wells, Wesley D. (Lorissa) Wells, Coleman (Laura) Wells, Benjamin C. (Rachel) Wells, Grady (Cheyenne) Maynard, and his only granddaughter, Paityn (Austin) Totillo. Additionally, Dale leaves behind 15 great-grandchildren, ten boys and five girls, who brought him great joy and pride.
Dale’s family will miss him dearly, and his legacy will live on in the hearts of all who had the privilege of knowing him. You will forever be remembered and cherished.