Wintersheimer was elected to the
Kentucky Court of Appeals in 1976, and to the
Kentucky Supreme Court in 1982, defeating appointed incumbent
John Jay O'Hara. He won reelection in 1990 and 1998. He was a prolific opinion writer, including opinions that established the constitutional basis for the family court in Kentucky, established the constitutional basis for economic development in Kentucky, established the tort of outrage in Kentucky, and established the guidelines for open records investigations in Kentucky. He taught business law at
Thomas More University before becoming an adjunct professor in constitutional law at
Chase College of Law for twenty years. In 2010, he published a memoir titled, "Secrets of the Kentucky Supreme Court." He died on February 18, 2021, in Covington. ==Electoral history==