Debra Ann Bailey

DEBRA ANN BAILEY, age 67, of Port St. Joe, Florida, passed away on August 9, 2025. She was born on October 5. 1957, to her mother, lona Smith, and father, James Bailey, and was affectionately known as "Deb" or "Debra-Ann”.

Very early in her childhood, Debra was taken in and raised as her own child by her sister, the late Emma Lee Chambers. This loving act brought her many "bonus" siblings, each of whom she loved dearly. Debra graduated from Port St. Joe Jr.-Sr. High School with the Class of 1976. Soon after, she welcomed her handsome son, Sean C. Bailey, into the world, and later, her two beautiful twin daughters, Tia and Tamara Chambers. Though she had three biological children, she also built a strong, cherished connection with Terrance Chambers, whom she loved as her own son.

Debra was renowned for her strong work ethic throughout her life. Her varied occupations included hairdresser, fast food worker, dry cleaning presser, and housekeeper. She found joy in fishing, parties, long car rides, movies, and swimming. Debra loved cooking and entertaining for friends and family, carrying her sweet and generous spirit of hospitality from St. Joe to Fort Myers.

She adored spending time with her grandchildren and took immense pride in becoming a great-grandmother. Her love for travel and outgoing spirit ensured she made a new friend wherever she went.

Debra is survived by her son, Sean Bailey, two daughters, Tamara and Tia Chambers, and two sisters, Sandra Bailey and Patricia Bailey. She also leaves behind three grandchildren, Cheyenne Bailey, Jaida Bailey, and Mason Bailey, a great-grandchild, Nico Prince Gilmore; and many beloved nieces, nephews, cousins, and friends.

She will always be remembered for her loving spirit, strong faith, resilience, loyalty, and kind heart.

Services will be held at Philadelphia Primitive Baptist Church in Port St. Joe, Florida on Saturday, August 30, 2025 with visitation beginning at 9:00 A.M. Eastern Time and the funeral at 10:00 A.M. Eastern Time. Burial will follow at Forest Hill Cemetery.

Arrangements are entrusted to the caring staff of Comforter Funeral Home in Port St. Joe, Florida.