Richard E. Olson

Richard Emil “Dick” Olson was born November 6, 1917, in Stoughton, Wisconsin, the son of Winton and Hattie Maxson Olson. He graduated from Stoughton High School in 1935 and married Dorothy Wright on July 16, 1938, beginning a marriage that would last more than 66 years.

During World War II, Olson enlisted in the U.S. Army Air Forces, entering service in July 1943. His military training took him to several locations, including Keesler Field, Mississippi; Mississippi State College; San Antonio, Texas; Amarillo, Texas; and Pratt, Kansas. At Amarillo Army Air Field, he completed technical training as an aviation mechanic, preparing him to maintain the B-29 Superfortress.

Olson was initially trained in connection with B-17 aircraft before being transferred to the B-29 program. He completed a transition course at Amarillo and was trained for duty as a member of a B-29 aircrew. Records later identified him with the 93rd Bomb Group, and a wartime newspaper account reported that he received a Presidential Unit Citation for his service. Another surviving clipping places Private Richard E. Olson with the 246th Army Air Forces Base Unit, Squadron D, at Pratt Army Air Field in Kansas. Olson was discharged from military service on November 20, 1945.

After the war, Olson returned to civilian life and became a familiar Stoughton businessman. Over the years, he owned or operated several businesses, including a Firestone store, a farm, and real estate and insurance operations. He became a special agent for Central Life Assurance Company and completed specialized life insurance training at Purdue University. His business career eventually included work in real estate, a field in which records still identify him in the early 1960s.

Olson also devoted considerable time to public and community service. He served as an alderman on the Stoughton City Council and remained active in a number of local organizations. His connection to American Legion Post 59 eventually led to his election as Post Commander. Olson was chosen Commander with Tony Malizio as First Vice Commander and Lloyd Emery Jr. as Second Vice Commander, with the newly elected officers scheduled to be installed June 22 and serve for one year. He also represented Post 59 as a delegate to the Wisconsin American Legion state convention in Madison.

Outside of his business and civic activities, Olson enjoyed fishing and hunting and was remembered for helping others. He and Dorothy raised four children: Marshall, Keith, Patricia and Melissa.

Richard E. “Dick” Olson died January 20, 2005, in Woodruff, Wisconsin, at the age of 87, surrounded by his family. He was preceded in death by his daughter Patricia and was buried at Riverside Cemetery in Stoughton. Military rites were provided by the American Legion Post 59 Honor Guard.

Perhaps the simplest description of Dick Olson appeared at the end of his obituary:

“He was liked by everyone.”

For a man whose life included wartime service, business ownership, city government and leadership of Post 59, that may be one of the nicest things that could have been written about him.