Watkins was born in 1887. He was the son of the Rev. Amos Watkins of the Trinity Episcopal Church in Bay City, Michigan. He attended Ann Arbor High School and next enrolled at the University of Michigan. He played at the tackle, fullback and center positions for the Michigan Wolverines football team from 1905 to 1909. He won a Rhodes Scholarship to study at the University of Oxford in 1909. Watkins later received a law degree from Detroit College of Law and began practicing law in Detroit. He also regularly returned to Ann Arbor to serve as an assistant coach to the football team under head coach Fielding H. Yost. During World War I, he served in the U.S. Army and attended the first training camp at Fort Sheridan. After the war, he became "one of Detroit's most respected attorneys."