Leonard Jackson Keeling

Leonard Jackson “Jack” Keeling, III, age 77, passed away unexpectedly in his sleep on Friday, August 21, 2026. Born in Harrison, Arkansas, on July 24, 1949, Jack was the son of L.J. Keeling, Jr and Arlene Keeling. He spent most of his childhood in Union City, Tennessee.

Jack attended the University of Tennessee, Knoxville, where he was a proud member of the ATO fraternity. After college, he began his career as a commodity broker with Southern Feed Ingredients. His entrepreneurial spirit eventually led him to establish his own business, bringing together his knowledge and success in the commodities industry with his lifelong passion for horses. From that vision, Windswept Enterprises in Collierville, Tennessee, was born.

A true AQHA horseman, Jack devoted countless hours to raising, breeding, training, showing, and enjoying horses. He and his family traveled throughout the country hauling horses to compete at local and national horse shows. For Jack, horses were far more than a hobby; they were a lifelong dream and a way to spend time with his girls. That brought him tremendous joy and happiness.

In his later years, after facing multiple health challenges, Jack made his home at The Brennity in Fairhope, Alabama. True to his outgoing personality and natural gift for making friends, he quickly earned the affectionate title of “The Mayor of The Brennity.” He loved welcoming newcomers, “breaking them in,” telling stories, making friends, and helping everyone feel at home.

Above all else, Leonard treasured his family. His three daughters and seven grandchildren were the greatest joys of his life. He cherished every visit, phone call, conversation, and opportunity to spend time with them. His family was at the center of his heart, and his love for them was unmistakable.

Jack was preceded in death by his parents, L.J. Keeling, Jr and Arlene Keeling. He is survived by his three daughters, Kim Shikle (Rich Abernathy), Jessica Hopper (Warren), and Jackie Etz (Brian); his seven beloved grandchildren, Keegan Hopper, Parker Shikle (Jordyn Behan), Riley Hopper, Chandler Hopper, Avery Etz, Lily Etz, and Stella Etz; his sister, Jean Jones (Ken) of Troy, Tennessee; and several nieces and nephews.

Leonard will be remembered for his entrepreneurial spirit, his passion for AQHA horses, his quick wit and storytelling, his ability to make friends wherever he went, and, most of all, the tremendous love he had for his daughters and grandchildren.

His family is heartbroken by his unexpected passing and will forever treasure the memories, stories, laughter, and love he gave them.

A Celebration of Life will be held Saturday, August 29, from

4:00–6:00 p.m. at:

Hope Farms Barn

915 Nichols Ave

Fairhope, AL 36532

Family and friends are invited to come together to celebrate Leonard’s life, share memories, and honor a man who was deeply loved and will be profoundly missed.