Henderson Bailey, 77, of Surry, Virginia, passed away on the 11th of August 2025 at the VCU Health after a brief illness. Born on the 26th of January 1948, in Waverly, to the late John W. Bailey and Avis L. Bailey, Henderson lived a life full of love, laughter, and dedication.  He was preceded in death by a dozen siblings, Norman Bailey, Wallace Bailey, Irvin Bailey, Percell Bailey, and Peyton Bailey; seven sisters, Ola Bailey Rice, Helen Harris, Esther Evans, Lillian Jackson, Avis McKnight, Millie Lyttle and Hazel Pierce.

A graduate of the Surry County Public School System, Henderson was a loyal employee of Smurfit Stone Container Company in Hopewell, Virginia, where he retired. He was a man of simple pleasures who had a profound love for collecting cars. He found serenity in hunting and solace in the tunes of old jazz and R&B music.

Known for his style, Henderson was a sharp dresser who always carried a big, warm smile. His charismatic personality and positive aura brought joy to everyone around him. He was a devout worshipper at Mt. Olivet Baptist Church in Petersburg, Virginia. His dedication to his faith was a testament to his strong character and moral compass.

Henderson's life was a tapestry of love and kindness woven together by the threads of his relationships. He was a beloved figure in his community and touched the lives of many with his generosity and compassion. He will be dearly missed, but his legacy will live on in the hearts of everyone he knew.

His memory will be cherished and kept alive by Al'Dwayne Drew (Sharon), Yolanda Drew, Cheryl Charity, and Deidra Anderson; his brother, Preston Bailey; his sister, Alvinia Thomas (Willie); his adored grandchildren, sweet great-granddaughters, and a host of nieces, nephews, cousins, and other relatives.

Services will be held 11:00 A.M., Saturday, August 23, 2025, at Mt. Olivet Baptist Church, 800 Augusta Avenue, Petersburg, the Rev. Dr. Wesley K. McLaughlin, Pastor and Rev. Herbert Holly II, Co-Pastor, eulogist. The interment to follow at the Bailey Family Cemetery.

J. M. Wilkerson Funeral Establishment, Inc., 102 South Avenue, Petersburg, VA, (804) 732-8911, www.jmwilkersonsince1874.com. Watch the funeral services live online on our J. M. Wilkerson Funeral Establishment, Inc. Facebook page.