Judge Bailey is a 1995 graduate of the University of Tennessee College of Law. He practiced law with the firm of Rogers, Laughlin, Nunnally, Hood and Crum from 1995-2006. In 2006 he was elected Greene County General Sessions and Juvenile Court Judge. He was re-elected in 2014 and 2022. He also presides over the Greene County Recovery Court program. He has been involved in many community organizations. Judge Bailey is a 7th Generation Greene Countian and his wife, Sandy, is also from Greene Co. They have 3 children.