Hale Holden was president of the Chicago, Burlington and Quincy Railroad from 1914 to 1918 and 1920 to 1929, and chairman of the board of directors for Southern Pacific Railroad from 1932 to 1939. He was one of the lawyers working for James J. Hill's defense team in the Minnesota Rate Cases. In later years he served as a director for a number of large companies including American Telephone & Telegraph, New York Life Insurance Company and the Chemical Bank & Trust.