Robert Cupp is in his second term as Criminal Court Judge, having been elected in 1998 and 2006. A Sullivan County native, Cupp graduated from Sullivan High School, and attended East Tennessee State University before transferring and earning his undergraduate degree at the University of Tennessee-Knoxville.

Cupp graduated from UT-Knoxville's School of Law and received his license to practice law in Tennessee in 1972.

As Criminal Court Judge, Cupp hears cases in four counties: Washington, Carter, Unicoi and Johnson.