In 1920, Chandler pitched a no-hitter for Grafton, North Dakota's team in the Red River Valley League. He attended a professional baseball tryout in Saskatoon but did not make the team. He returned to Transylvania and received a Bachelor of Arts degree in June 1921. He then signed with the Class D baseball team the Lexington Reds, where he was a teammate of future Hall of Famer Earle Combs. Briefly considering a career in baseball, he finally decided to study law. He entered Harvard Law School that same year, paying his way by coaching high school sports in Wellesley, Massachusetts. His former teammate Charlie Moran, then coaching the Centre College Praying Colonels football team in Danville, Kentucky, asked him to scout the national powerhouse Harvard Crimson, an upcoming opponent for Centre. Chandler took copious notes for Moran, and Centre defeated Harvard 6–0 in what is considered one of the greatest upsets in college football history.