Robert Kenneth Bailey

Robert Kenneth Bailey, 82, of Pensacola, passed from this life on Thursday, September 26, 2025, and entered his heavenly home where he was reunited with many of his loved ones. He was born on December 31, 1942, in Pensacola, Florida.

Robert met and married the love of his life, Loleeta Carr Bailey Smith. They later divorced but always remained close friends. They raised their children, grandson, nieces and nephews and always had an open-door policy with plenty of love to share.

Robert worked hard his whole life and retired from the Escambia County School Board. He lived in Milton for several years, before returning to Pensacola to be closer to his daughters. He was very generous with his time and money. He loved to share in his son's, grandsons' and great-grandson's (Robby, Bo, Henry & Laedyn Bailey) love for car/truck racing and even ventured into race car driving. He shared his skill in dancing and singing with all his family and friends. Not only his presence, but his voice will be missed by many of us.

Robert taught all of us that grew up or around him to enjoy life. We spent many summers riding the dune buggy over the dunes at the beach. Many moons spent in tents perched oceanside under the moonlight listening to him sing, and mom fish, with the smell of fresh fish cooking. We would body surf, crab, fish, sing and dance from sunup to sundown. He always loved having his kin folks near him.

Robert gave us all unconditional love. He had a way of letting us know just how much we meant to him. His family was his everything. He was very thankful to all those that took such great care of him in his time of need.

Robert was preceded in death by his father, Henry O. Bailey; mother and stepfather, W.G. and Carrie B. Stacey; brothers: Owen H. "Pedee" Bailey, Hayward G. Bailey, and William E. Stacey; sister, Dorthy Mae Cedotal; wife, Loleeta C. Bailey Smith; son, Robert "Robby" Bailey; daughter, Tina M Bailey; and two great-grandchildren.

He is survived by daughters, Loretta Bailey and Anita Bailey; grandchildren: Joshua Griener (Ryan), Bo Bailey (Jessica), Cristie Crider (Casey), Christopher McConaghy, Zack Valadao (Britt), and Henry Bailey (Autumn); and thirteen great-grandchildren.

Visitation will be held from 11:00 a.m. until the funeral service begins at 1:00 p.m., all on Tuesday, September 30, 2025, at Trahan Family Funeral Home, Milton Chapel. Interment will follow at Crain Cemetery.

Pallbearers are grandsons: Joshua Griener, Bo Bailey, Christopher McConaghy, Zack Valadao & Henry Bailey; and great grandson, Laedyn Bailey.

Robert is missed and leaves a void in many of our hearts!