Major-General Freeman is a native of Toronto, ON. He joined the Royal Canadian Air Force in 1952 and attended Royal Roads Military College, Royal Military College, and University of Toronto where he obtained a Bachelor of Applied Science in Civil Engineering in 1957. Following training as an Air Observer, in 1958, he flew with 440 All-Weather Fighter Squadron on CF 100 Interceptors at Zweibrucken, Germany. In 1959 he transferred to the Construction Engineering Branch and was assigned to 30 Air Movements Base, Langar, England. In 1962, following completion of RCAF Staff School, Toronto he joined the Directorate of Civil Engineering at Air Force Headquarters, Ottawa.

In 1964, Major-General Freeman was promoted squadron leader and became Station Construction Engineering Officer at RCAF Station Uplands, ON. He was a student at RCAF Staff College, Toronto, 1965-66 and then served as Technical Services Officer at Canadian Forces Base. In 1967 he was assigned to the United States Air Force on exchange duties in the Directorate of Civil Engineering at The Pentagon, Washington, D.C., and promoted wing commander. In August 1970, he became Director of Construction Engineering Control at Canadian forces Headquarters.

Promoted to the rank of colonel in July 1972, he was assigned to Air Transport Command Headquarters, Trenton, ON, initially as Command Construction Engineer and later as Deputy Chief of Staff, Technical Services. In July 1975, he was appointed Command Engineer in the newly formed Air Command HQ in Winnipeg. He was promoted to brigadier-general in October 1976 and named Director General Quartering at National Defence Headquarters. In September 1977 MGen Freeman was appointed Chief of Construction and Properties. He retired from the Canadian Forces in 1982 to work as an engineering management consultant. In 1987 he joined the Department of Public Works as Assistant Deputy Minister Architectural and Engineering Services until 1990. He is on the Board of Directors of Defence Construction Canada and the Marine Society of South Marysburgh, ON.

In October 1991, MGen Freeman was appointed Colonel Commandant of the Canadian Military Engineers.