Born in Warrenton, Missouri, Randolph became a typesetter in 1912, also joining the International Typographical Union (ITU).
In his spare time, he studied at the Webster College of Law, and was admitted to the bar in Illinois in 1921.
He remained active in the ITU, and in 1927/1928 served as president of the Chicago Typographical Union local.
Under his leadership, there was a major ITU strike in Chicago, which succeeded in retaining the closed shop there.
Randolph subsequently created Unitypo, a union newspaper for distribution in cities where the ITU was on strike.