Bailey received his B.A. (1924), M.A. (1925), and Ph.D (1927) from Stanford University, where he was also elected to Phi Beta Kappa. His doctoral work was in U.S. political history. He switched his emphasis towards diplomatic history while teaching at the University of Hawaii. After three years at Hawaii, he taught American history for nearly 40 years at Stanford and also served as a visiting professor at Harvard, Cornell, the University of Washington, and the National War College in Washington, D.C. He retired in 1968.