Sylvester "Chuck" Bailey

Sylvester "Chuck" Bailey, 77, beloved husband, father, brother, and friend, passed away on November 3, 2023. He was born on February 18, 1946, in Pittsboro - Calhoun County, MS, to the late Jessie Fox and Ester Bailey.

Sylvester will always be remembered for his kind and gentle nature. He touched the lives of countless individuals through his generosity and compassion. His warm smile could light up a room, and his presence brought comfort to those around him.

Growing up in Mississippi with his late brothers Johnny, Jerry, John, and Charles, as well as his late sister Thelma Moon, Sylvester learned the importance of family. He cherished the bond they shared and often reminisced about their childhood adventures together. Sylvester's love for his family was unwavering and anchored him throughout his life.

Sylvester was united in marriage with the love of his life, Carrie Bailey. As a father to his sons, Bernard Warren, Russell Kelly, Timothy Kelly; and step-daughters, Demetria Davidson, and Angela Davidson, Sylvester was a pillar of strength and support. He instilled in them the values of hard work and perseverance while encouraging them to pursue their dreams. Sylvester's love for his children knew no bounds.

Beyond blood relations, Sylvester cherished the friendships he formed over the years. His kindness attracted others to him like a magnet. Those lucky enough to call him their friend knew that loyalty and trust were guaranteed when it came to Sylvester "Chuck" Bailey.

Visitation will be held on November 12, 2023, from 12:00 PM to 1:00 PM at Oak Grove Church, located in Bruce, MS. Following the visitation, a funeral service will be conducted at the same location at 1:00 PM. All those who knew and loved Chuck are welcome to attend these events and pay their respects.

Sylvester's memory will forever be cherished by his loving wife Carrie Bailey; his children Bernard Warren, Russell Kelly, Timothy Kelly, Demetria Davidson, and Angela Davidson; his brother Roger Bailey; his sister Sarah Gray; as well as numerous extended family members and dear friends.


Sylvester "Chuck" Bailey may no longer be with us physically, but his spirit lives on in the hearts of all those who had the privilege of knowing him. His genuine love for others and his unwavering dedication to his family will forever serve as an inspiration. May he rest in eternal peace.