Timothy M. Cunningham was born on May 4, 1921. He attended Catholic grade and high schools in St. Paul, Minnesota. When World War II started, he entered the Army Air Corps as a flying cadet. After graduating, he was assigned as a flight instructor, and later became a B-24 Airplane Commander.

After the war, he was an Air Force Reserve Pilot, and also worked as a civilian flight instructor until he was hired by the FAA as an Air Traffic Controller. He served as an Air Traffic Controller in Minneapolis, San Antonio, Burbank, and San Diego. He retired in San Diego after 30 years and went to work as a flight instructor for the Armed Forces Aero Club at Montgomery Field, San Diego. He also became an accident prevention counselor in the San Diego area. He obtained teaching credentials for the State of California, and was employed for one year as a part-time teacher at Mesa College in the Aeronautical Department. Later, he was hired by his friend Ted Steckbauer at Brown Field where he worked as a technical writer, flight instructor, glider pilot, tow pilot, and ground and flight simulator instructor.

When he discovered that there was an aerospace museum restoration shop in San Diego, in 1978, he became a volunteer at the San Diego Aerospace Museum, and helped with restoration of such airplanes as the Ryan SC and the Ryan M-1, Spirit of North Dakota, and the building of the Spirit of St. Louis III. He later joined the museum staff where he worked for more than 30 years as Restoration Supervisor, and later Restoration Director. He was also a member of the museum's Exhibit Committee. He was dedicated completely to doing all that he could to make the museum a truly outstanding San Diego landmark.