Charles Shelton "Cowboy Chuck" Kelly Jr.

Charles "COWBOY CHUCK" Shelton Kelly Jr. September 19, 1951 – August 31, 2025
On September 19, 1951, a legend was born. Charles "Cowboy Chuck" Shelton Kelly Jr. came into this world in Norfolk, Virginia, and passed peacefully at home on August 31, 2025, at the age of 73 in Chesapeake, Virginia.
Chuck was the third oldest of seven children, growing up with his five sisters-Kathleen, Koleen, Kay, Kim, and Kia-and his brother, Marty. He spent much of his youth on his grandpa John Henry's farm in Roanoke Rapids, carrying those country roots with him throughout his life.
He attended Ingleside Elementary, Princess Anne High School, and Frederick Military before graduating from Barry Robinson. On the football field, he became known as one of the hardest-hitting linebackers around. According to teammates like Michael Romano, Chris and Steve Sakis, he never failed to knock at least one opponent out of the game every Friday night. His son Cody often heard him say, "If I'd been just a little taller, I would've been in the NFL." One of his favorite memories was visiting the Football Hall of Fame with Cody and meeting linebacker legend Dick Butkus-whom he was often compared to during his football career.
Chuck's toughness wasn't confined to the gridiron. He trained at Wearing's Gym in Virginia Beach, where he once sparred with heavyweight champion Joe Frazier-who admitted Chuck took his best shots without going down. His feats of strength became family lore, including the time he lifted the front of a Volkswagen above his head.
In his younger years, Chuck lived life as a renegade-working as an enforcer and owning more than 20 motorcycles. He rode with Bill Stancil, his wife Barbara, and many others. He claimed he never lost a fight, and those who knew him believed it. When he learned Pamela Dillon was pregnant with their son, Chuck traded in his "iron horse" for a four-legged one and began writing a new chapter of his life. On October 9, 1991, Cody was born, and fatherhood became Chuck's proudest role.
Chuck later married Pamela Dillon in his parents' backyard. Though they eventually went their separate ways, they shared years of love and the joy of raising Cody. He worked tirelessly at Mid Atlantic Coatings Inc. alongside Mike Leanzo, Gus Angelopoulos, Greg Williams, Kenny Matthews, Pulusi "Bruce" Loane, William "Tennessee" Morse, Jim Berry, Larry "Grant" Gordy, Charlie Burke Sr. and Jr., Gary Haskins, and many others. A natural leader, he was respected for his work ethic, sense of humor, and ability to inspire loyalty. He often told his son that he worked so hard so Cody would never have to.
Later, he moved his family to Wedgewood Dr. in Suffolk, where the property became known as the "DOUBLE C RANCH." Horse riding, fishing, swimming, hunting, and Sunday cookouts turned into weekly gatherings for family and friends. He welcomed many of Cody's friends and treated them as his own. To so many, he was a father figure. He was also "Coach Chuck"-whenever Cody played a sport, Chuck was the head coach. He worked all day, came home, cooked dinner as a single dad, cared for the horses, maintained the property, and still showed up as both coach and father. Not once did he complain or show stress. A real cowboy-the very definition of a man.
Outside of work, Chuck's passions were as bold as his personality. He immersed himself in Civil War reenactments, where he found lifelong friends like Ray "Bone" Bailey and Wally Faison-the "Three Musketeers." Later, he discovered team penning and sorting, earning buckles and cash prizes while building another family of friends in the horse world, including Mark Adcock, his wife June, and their children Taylor and Haley; Ray and Lisa Norman and their daughter Lauren; Jeanette Fowler and the whole staff at South Point Saddlery; Dallas Weeks; Jimmy and Faith Rogerson; Bishop Russell; Earl Bateman; Earlene Gregory; Steve and Terry Temple; and so many more.
Chuck grew up Presbyterian and carried pieces of that faith with him, even as he carved his own path. In his final days, his daughter-in-law, Ebonee Kelly, lovingly guided him as he confessed Jesus Christ as his Lord and Savior-bringing peace and strength to his fearless spirit.
Beneath the tough exterior, Chuck had a soft heart-especially for kids, women, and his two grandchildren, Mason Dillon Kelly and Makai Shelton Kelly, who became the pride and joy of his later years.
To many, Chuck was more than a father, brother, or friend-he was a role model. Cody's friends admired him deeply, often looking to him for wisdom, guidance, and strength. "Uncle Chuck" welcomed anyone into his home with open arms, reminding them, "Don't be bashful," as he pulled up a chair at the dinner table. Chuck would give you the shirt off his back, not for accolades or recognition, but out of pure love. He genuinely loved, and when he loved, he loved unconditionally. He touched countless lives and made everyone feel like family.
Chuck was cut from a different cloth-a rare breed, one of a kind. Fearless in everything he did, he shocked doctors time and again with his incredible pain tolerance and resilience, leaving many amazed at just how tough he truly was.
He was preceded in death by his parents, Charles Shelton Kelly Sr. and Bettie Josephine Wood Kelly. He is survived by his son, Cody Kelly; his daughter-in-law, Ebonee Kelly; his two grandchildren, Mason Dillon Kelly and Makai Shelton Kelly; his brother, Marty, and his wife Kim; and his five sisters: Koleen, with her two sons, David and Roger; Kathleen, with her two daughters, Kelli and Kasey; Kay and her husband, Paul, with their daughters Gabrielle and Alicia and their son Philip; Kim and her husband, Wes, with their daughter Kirsten; and Kia and her husband, Donald, with their daughter Emily and son Stephen. He also leaves behind many great-nieces and nephews he loved and adored, along with countless friends who knew him not only as a fighter and big-hearted hero, but as a true legend-a word most often used to describe him.
A celebration of Chuck's life will be held on what would have been his 74th birthday, September 19, 2025, at River Oak Church, beginning at 6 p.m. Friends, family, and anyone Chuck knew or impacted are invited to share stories and honor a man who lived courageously, loved deeply, and left an indelible mark on everyone he met.
May he rest in peace, remembered forever for his heart of gold, his unwavering spirit, and the legendary life he lived with no regrets. You will always live on through those whose lives you changed and touched.
"LEGENDS NEVER DIE Chuck's body may have left this earth but his EXAMPLE lives on forever his INSPIRATION lives on forever his SPIRIT lives on forever his LEGACY lives on forever..." To send flowers to the family or plant a tree in memory of Charles "Cowboy Chuck" Shelton Kelly Jr., please visit our floral store.