Harold Dean Whipkey was born January 25th, 1940, in Sayre, Oklahoma to Katie Mae (Wylie) and Elmer Harold Whipkey. He passed from this earthly life and entered the gates of heaven on Saturday, February 12th, 2022, in Kingston, Oklahoma at the age of 82 years and 18 days. Harold grew up in the Mayfield community and attended school at Sweetwater, Oklahoma graduating in 1958. After high school graduation, he attended Sayre Junior College where he played basketball and obtained his associates degree. He continued his education at Central State University where he continued playing basketball for the Bronchos while obtaining his Bachelor of Science in education. He married Norma Jean Callen in 1958, in Erick, Oklahoma. Harold began his career in education in Fort Supply, Oklahoma where he coached for five years. He and Norma and their two young sons, Ron and Roger, eventually settled in Aline and then later Cleo Springs, where Harold was the high school principal and junior high coach for Aline-Cleo schools. While at Aline-Cleo, Harold obtained his master's degree in in Education Administration from Northwestern Oklahoma State University and became the superintendent of Aline-Cleo schools. In 1992, he left Aline-Cleo to become the superintendent at Higgins, TX and was there until he retired in 2005. Harold married Cathie (Diel) in 1995 and they made Higgins their home. Harold enjoyed watching his grandchildren at sporting events, quail hunting out at his family farm, fly fishing with his boys in Colorado, and spending any time he could on the golf course. Harold is preceded in death by his parents, his first wife Norma in 2002, and his second wife Cathie in 2020. Harold is survived by his two sons, Ron Whipkey and wife Holly, of Kingston, Ok and Roger Whipkey and his wife Rebecca, of Lubbock, TX; Six grandchildren, Benjamin Whipkey, Mason Whipkey, Jacob Whipkey, Ashlie Allmendinger, Reagan Whipkey, and Rylee Whipkey; two great grandchildren Karter and Karsyn Allmendinger; stepdaughters Casie Brownlee, Kimberly Scrogin, and Kristina Redman. Funeral services will be held Friday, February 18th, 2022 at 2:30 PM at the Sweetwater First Baptist Church. Burial will immediately follow at the Mayfield Cemetery under the direction of Chris Whinery and the staff of Affordable Cremation Service-West. Condolences can be made online at www.classicfunerals.com. There will be visitation at The Sweetwater First Baptist Church Friday from 9:00 A.M – 1:00 P.M. The family will be available to greet friends from 12:00 P.M. – 1:00 P.M. Coffee, drinks and snacks will be provided.