He retired after serving for four years as the chairman of the powerful United States House Committee on Rules.

[1] In April 1941, Bolling entered the United States Army as a private and served until discharged as a lieutenant colonel in July 1946, with four years' overseas service as assistant to the chief of staff to General Douglas MacArthur in Australia, New Guinea, Philippines, and in Japan.

He was twice a candidate for House Majority leader, losing to Carl Albert in 1961 and to Jim Wright (by three votes) in 1977.

During the 1970s, Congressman Bolling owned a cottage on St. Barthelemy in the French West Indies, which he also rented to other vacationers.

[9] He subsequently married Jim Grant Akin, a Congressional liaison officer for the U.S. Department of Health Education and Welfare, who later served as his legislative affairs assistant.