 Before joining the Ohio Supreme Court, Cupp gained appellate judicial experience as a judge on the Ohio Court of Appeals (Third Judicial District) from 2003 to 2006.Cupp was a member of the Ohio Senate for 16 years, 1985–2000, but was forced to retire due to legislative term limits.He was President Pro-Tem of the Senate from 1997 to 2000, the second highest-ranking leadership position in the Senate.