Douglas M. Wynn Sr.

Douglas Monroe Wynn Sr. 71 of Jennings FL, passed away February 23, 2026 at Haven Hospice surrounded by his loving family.

Doug was born in Jacksonville Florida to James Louis (JL) Wynn and Maggie Sheffield Wynn on October 14, 1954. He graduated from Hamilton County High School in Jasper FL in 1972. Doug was an avid baseball and football player. He also loved to hunt, fish and scuba dive. If there was water around he was in it one way or the other. He was raised on his family’s farm, where he discovered early the work that would shape his life and character. The land was not just where he grew up, it was where he learned the value of dedication, resilience, and pride in a job well done. Farming wasn’t simply his livelihood, it was what he loved and he carried that passion with him throughout his life.

An exceptional farmer, he understood that success came from patience, perseverance, and faith in the work of his own hands. Those same qualities made him a gifted mechanic and entrepreneur. Over the years, he owned and operated businesses with the same integrity and determination that defined his life. There was little he couldn’t fix.

He was known as a fixer of all things and a tireless worker, someone who showed his love through action. His hands built, repaired, and restored; his work ethic set an example for everyone around him. Above all, he took pride in providing for his family and in doing honest work each and every day.

He is survived by his loving wife Glenda Stapleton Wynn, son Doug Jr (Kasey) Wynn of Live Oak Fl, daughter Stacey (Garrick) Wood of Iowa Park, TX, his brother Eddy Wynn (Jackie) of Jennings, FL. Six grandchildren that he adored, Sidney Nicole Wynn, Blake Douglas (Emma) Wynn, Braxton Lee Wynn of Live Oak FL and Madison Alexis Wood, Malorie Grace Wood, and Micah Logan Wood of Iowa Park TX. He is also survived by brother-in-law and sister-in-law John and Teresa Oliver, David Stapleton (Sue Eplin) and Robert Stapleton, and dear to his heart, Vern Raulerson and Dale Myrick, and numerous aunts, uncles, cousins, nieces, and nephews.

Doug was preceded in death by an infant daughter, Carrie DeAnna, who was stillborn at birth, his father and mother JL and Maggie Wynn.

Memorial services will be held Saturday, February 28, 2026, at 10:00 a.m. at Jennings Community Church (former Jennings United Methodist) 1371 McCall St. Jennings, FL 32053