Although he was expelled from high school and admitted to Oregon State University on a provisional basis, Jackson received a bachelor of science degree in 1925.

Jackson had a stint in military service in World War II, during which he attained the rank of colonel in the United States Army Air Forces.

Jackson served as Executive Officer under Ira C. Eaker, commander of the Eighth Air Force, in Italy.

Among the decorations he received were the Bronze Star, Legion of Merit, Order of the British Empire, and Crown of Italy.

[2] He was also a director of Standard Insurance Company, the U.S. National Bank of Oregon, Fred Meyer, Inc., and the U.S. Chamber of Commerce.

[6] Jackson leased, then purchased, in 1946, a fashionable Colonial Revival house in Medford that was designed by noted architect Frank Chamberlain Clark.