He was educated at Harvard University, receiving a B.A. in 1947, an M.A. in 1948, and a Ph.D. in 1952.

Ambassador Hugh Montgomery enlisted in the U.S. Army in 1942 and parachuted with the Pathfinders of the 505th Parachute Infantry Regiment of the 82nd Airborne Division into Normandy on D-Day. He was wounded at the battle of the Falaise Pocket

--the decisive battle of the D-Day engagement. Being released from the hospital a few weeks later, the then Sergeant Montgomery was told to report to a special counterintelligence detachment (X-2) of the OSS (probably due to his fluency in "eight or nine languages"); but, he was never told this unit was part of the OSS.

His OSS missions behind German lines included attempting to locate and free American POWs, searching for German atomic scientists and capturing a German baron in Munich who was a major supporter of the Nazi party. In April 1945, Sergeant Montgomery's four-man team accidently discovered the Buchenwald concentration camp while operating behind enemy lines and radioed for urgent medical assistance. Sergeant Montgomery was given the black SS flag that flew over the camp by its grateful inmates. He still has this flag which he plans to donate to a future National OSS Museum of American Intelligence and Special Operations. Following the war, Ambassador Montgomery had a storied career with the CIA's Operations Directorate, serving in senior posts in Rome, Vienna, Moscow and other capitals. He was the principal assistant to the CIA Berlin chief for the Berlin Tunnel operation in the 1950s that tapped underground cables being used for Soviet communications. He served in Moscow during the time of Oleg Penkovsky, a high-ranking Soviet military intelligence officer, while Penkovsky was one of the most valuable assets in the Agency's history. Ambassador Montgomery held many senior positions at the State Department and the CIA during the second half of his career. In 1985, he was made a U.S. deputy ambassador to the United Nations which allowed him to serve with his longtime friend General Vernon Walters who was named America's principal UN ambassador that year. Ambassador Montgomery returned to the CIA after Walters stepped down in 1989 and held several high-level posts advising CIA directors in Democratic and Republican administrations during the final 25 years of his career. Ambassador Hugh Montgomery was the Chairman of the Office of Strategic Services Society and the 2015 recipient of the society’s Donovan Award.