Winston C. Bailey

Winston C. Bailey, of Glasgow, Kentucky, passed away on September 27, 2026, at his residence in Glasgow, surrounded by his loved ones. He was born on November 18, 1941, in Glasgow, Kentucky to the late Edgar Bailey and the late Nora Lee Boles Bailey.

Mr. Bailey served his country with honor in the United States Army as a paratrooper in the 82nd Airborne. Following his military service, he devoted 26 years of work to Eaton Brake in Glasgow, Kentucky, remaining there until his retirement in 1994.

Retirement suited Winston well, and he became especially known for his handyman skills. He loved working on things and was often the first person his grandchildren called when they needed something hung up or made for them. He also loved to mow and took great enjoyment in doing so. Above all, the time he treasured most was time spent with his grandchildren and loved ones. He was deeply proud of his sons and of all those in his family.

He is survived by his beloved wife, Charlene Bailey, with whom he shared 61 years of marriage. He also leaves behind his sons, Carlos Bailey and Daylan Bailey (Tosha). His memory will be cherished by his grandchildren, Donte Gatewood, Santana Bailey, Daylan Edmonds, Mallory Bailey, and Raegan Bailey, and by his great-grandchildren, Brooklyn Edmonds and Layla Edmonds. He is also survived by his brothers, Fred Bailey, Rex Bailey, Jimmy Bailey, and Billy Allen, and by his sister, Janet Page. He will be remembered with love by his family and all who knew him.

In addition to his parents, he was preceded in death by his brothers, Roger Bailey and Rondel Bailey; and his sister, Hattie Hansford.

A graveside service will be held on October 2, 2026, from 11:30 a.m. at Oak Grove Cemetery under the direction of A.F. Crow and Son Funeral Home.Military honors will be provided at the Glasgow DAV Chapter #20.

Winston C. Bailey will be remembered as a devoted husband, proud father and grandfather, faithful worker, veteran, and a man whose hands and heart were always ready to help the people he loved.