Herbert Lee Bailey, Sr., 63
November 12, 1962 – March 24, 2026
“As for me, my life has already been poured out as an offering to God.
The time of my death is near.
I have fought the good fight, I have finished the race, and I have remained faithful.” 2 Timothy 4:6–7
Herbert Lee Bailey, Sr., entered this world on November 12, 1962 unto the union of his parents, Walter Lee Bailey and Clara Green Dabbs, in Lee County, Mississippi, and transitioned to be with the Lord on March 24, 2026 in the evening in Green Oaks, Illinois doing what he loved, traveling caring a load in his truck, providing for his family whom he loved dearly, at the age of 63.
Herbert was a proud graduate of Pontotoc High School, Class of 1981, where he showcased his athletic spirit as a member of the football team. He also developed discipline and strength through his involvement in martial arts.
He found joy in life’s simple pleasures—cooking, driving across our beautiful country as a truck driver, and touching lives by sharing the Word of God. Above all, Herbert was a devoted family man and friend whose life was deeply rooted in love, care, and unwavering dedication to those he cherished most.
Herbert loved serving the Lord and was ordained as a deacon. Herbert was a charming presence and a jokester, never met a stranger; you would feel like you had known him forever. This is the lasting impression he would leave with you.
Herbert traveled the roads as a truck driver, enjoying doing what he loved for thirty-one years. His handle name, known by other truck drivers on the road, was Mississippi Deacon
Aug 2012, Herbert married the love of his life, Jennifer Denise Curtis and through this union, God beautifully brought their blended family together, formed a new household unit, and made it work.
To cherish his life and carry on his legacy, he leaves his wife of fourteen years, Jennifer Denise Bailey; 19 children, Chiquita Dominis –Yourbatis(Johnson), Sheena Ivy (Shyne) of New Orleans, LA, Herbert Bailey, Jr. of West Point, MS, Shelby Bailey of California, Amelia Baker, Stephen Bailey, Jocelyn Brown, Jameisha Brown, and Andrew McGaughy, all of Tupelo, MS, Rachel Bailey of Saltillo, MS, Ashley Bailey, Phillip Bailey of Tupelo, MS, Shannon McGaughy of Guntown, MS, Scherella McGaughy of Belden, MS, Sonya McGaughy of Tupelo, MS., Nicholas Betts (Jasmine) of Anderson, IN, Shermila Betts of Horn Lake, MS, Keivonte Smith (Alina) of Germany, Jakierra Brown of Orlando, FL; mother, Clara Dabbs of Tupelo, MS; siblings, Lenora Elzie of Thaxton, MS, Glynis Bailey and Johnnie Ruth Bailey of Tupelo, MS; special sons, Chindeu Ufio and Rodney Crump Jr.; a sister and brother in law, Gregory and Latasha Metcalf; three God-daughters, Baleigh Lucas, Karleigh Ware, Emori Ware. 48 grandchildren and a host of other relatives, and many friends.
Herbert was preceded in death by his father, Walter Lee Bailey; grandmother, Ceola Green; and granddaughter, Faith Ivy.
Honorary Pallbearers – Phillip Bailey, Stephen Bailey, Herbert Bailey, Jr., Andrew McGaughy, Shelby Bailey, Keivonte Smith
Active pallbearers – Servantes McGory, James Harps, Gregory Metcalf, Anthony Rogers, Fredrick Curtis, Justin Ware
Flower bearers- The Women of Life Changing Ministries and Pontotoc High School Class of 1981
Please follow the funeral home link above for further information, or to send online condolences or memorial gifts.
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Viewing
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Celebration of Life Service
