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Born in Clinton, Oklahoma in 1953, Winchester received his Bachelor of Arts from the University of Oklahoma and his Juris Doctor from Oklahoma City University. After graduating from law school, Winchester practiced law in Weatherford, Oklahoma, and Hinton, Oklahoma, before being named Associate District Judge for Caddo County, Oklahoma in January 1983. In December 1983, at age 30, Winchester became one of the youngest district judges in the state when he was appointed as District Judge for the Sixth Judicial District of Oklahoma. During his tenure as a district judge, he tried more than 200 jury trials, ranging from fraud to first-degree murder death-penalty cases.
Winchester was named Outstanding State Trial Court Judge by the Oklahoma Trial Lawyers Association in 1986 and served as an executive board member of the Oklahoma Judicial Conference from 1992 to 1996. He also served as President of the Oklahoma Judicial Conference in 1995. From August 1997 to January 2000, Winchester served as a United States Administrative Law Judge. While in these positions, he established the second in-state program for Children Coping With Divorce to assist children during difficult times.
Governor of Oklahoma Frank Keating appointed Winchester to the Oklahoma Supreme Court on January 4, 2000. In 2007, the eight other Justices of the Oklahoma Supreme Court elected him to serve a two year term as Chief Justice of Oklahoma.
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