He was hired as co-pilot and flight engineer with Northeast Airlines in 1958, and retired in 1987 as captain with Delta Airlines. He also operated a popular Christmas tree farm on Silver Street in Great Barrington for many years.
The family moved the Dempsey's Garage business to Great Barrington in 1937, operating on Railroad Street until 1947 when Mr. Dempsey and his brother, Matthew J. Dempsey Jr., took over the business and moved it to 42 Bridge St.
He enlisted in the U.S. Army in August 1942, served as a military policeman in Italy, and was awarded the European African Middle Eastern Service Medal.
