After a year, Chandler was not able to afford Harvard. He returned to Kentucky and continued at the University of Kentucky College of Law, coaching high school sports in Versailles and served as the head coach of the women's basketball at the University of Kentucky in 1923. He was an assistant coach and scout for Charlie Moran at Centre, and he coached the freshman football team there. A member of the Order of the Coif, he received his Bachelor of Laws degree in 1924. He was admitted to the bar the following year and opened his law practice in Versailles.