By Philip R. Devlin
(October 21, 2022) — Sixty years ago this week, the Cuban Missile Crisis played out for thirteen tense days in October of 1962. At Premier Nikita Khrushchev’s urging, the Soviet Union shipped intermediate-range missiles armed with nuclear warheads to Cuba– far more powerful than the atomic bombs dropped on Hiroshima and Nagasaki. Cuban dictator Fidel Castro, still seething at America for sponsoring the disastrous Bay of Pigs invasion in 1961, welcomed the missiles with open arms. The presence of nuclear missiles just 90 miles from Florida, however, greatly alarmed Americans and brought the world to the brink of nuclear war.
U-2 spy planes (photo above) confirmed the presence of the missiles, and in one of the most important presidential addresses ever given, President John F. Kennedy informed Americans of their threatening presence on Monday night October 23, 1962. The Joint Chiefs of Staff, led by Air Force General Curtis LeMay, strongly advocated bombing and invading Cuba to remove the threat. Others, such as JFK, United Nations Ambassador Adlai Stevenson, and Secretary of State Dean Rusk, wished to explore a diplomatic solution to the crisis.
The diplomatic solution required time, but the public and political pressure for immediate action was enormous. The very next day Kennedy ordered the military to stand ready at DEFCON 2, the first time in history that the military had been ordered to that heightened alert. (DEFCON 1 is nuclear war.) Thanks in part to the critical actions of a CIA operative and World War II hero from Windsor Locks named Hugh Montgomery, JFK knew that time was on their side. The Kennedy administration aggressively pursued the diplomatic solution while imposing a naval quarantine on Russian shipping to Cuba.
Born in Springfield, Massachusetts on November 29, 1923, Hugh Montgomery (photo above) lived at 42 Elm Street in Windsor Locks. His grandfather, J.R. Montgomery, founded the Montgomery mill on the canal bank in 1871. Hugh attended Windsor Locks public schools from Kindergarten through 8th grade and then commuted to Loomis for secondary school. His mother taught foreign languages at Smith College, and Hugh inherited her aptitude for learning languages. By the time he had graduated from Harvard, Montgomery was fluent in eight languages, including Russian—a factor critical in his role during the Cuban Missile Crisis.
Following the attack on Pearl Harbor, Hugh joined the Army and became a member of the 82nd Airborne Division; in fact, he parachuted into Normandy on D-Day. He was wounded in the leg in France during the Battle of the Falaise Pocket in August of 1944, a wound that caused him to limp for the rest of his life.
Montgomery’s proficiency in French and German was not lost on his superior officers, and he soon became part of the OSS—the forerunner of the CIA. He was sent on several key spy missions into Germany; in fact, his undercover four-man team was the first to discover the horror of the Buchenwald concentration camp in April of 1945. He broke radio silence to obtain medical aid for the emaciated prisoners there.
After using the GI Bill to complete his Ph.D. at Harvard, Hugh was recruited to join the CIA in 1953. He remained with the CIA until 2014 when he retired at 91, having served more than 60 years in the agency. Regarded as a “founding father” of the CIA, Montgomery amassed numerous awards in his long career. He served in many diplomatic posts all over the world, but none would equal the importance of his presence in Moscow in 1962.
Montgomery’s main job in Moscow was to help manage a Russian double agent named Oleg Penkovsky.
A decorated World War II military hero, Penkovsky (photo above) had grown embittered at his inability to get promoted and grew disenchanted with Soviet Premier Khrushchev’s policies. He decided to defect to the West. Historians regard Penkovsky as one of the most important spies of the 20th century.
Hugh Montgomery had arranged a “dead drop” with Penkovsky at a 4th of July party at the American embassy in Moscow in 1962. Penkovsky was to leave a packet of important material for Montgomery taped to the inside bottom of a toilet tank lid in a bathroom at the embassy. Montgomery’s retrieval of the packet became eventful, however, as the toilet tank was an older model located high on a wall for gravity feed. Hugh first stood on the toilet seat to reach it, but the seat was made of wood and splintered. He resorted to standing on the wash basin and successfully reached the packet but fell back as the sink separated from the wall. Montgomery personally translated the Penkovsky documents and promptly sent them to CIA headquarters where the director took them to President Kennedy.
It is hard to overstate the importance of Penkovsky’s role in helping JFK defuse the missile crisis. Cold War historian Jerrold L. Schecter put it this way:
“His contributions changed American and British thinking about Nikita Khrushchev’s strategic nuclear capabilities and intentions. Penkovsky’s material made it clear that the USSR lacked the nuclear missile capability Khrushchev claimed, thus enabling President Kennedy to call Khrushchev’s bluff. During the Berlin crisis of 1961 and the Cuban Missile Crisis in 1962, Penkovsky was the spy who saved the world from nuclear war.”
It is also hard to overstate the importance of Windsor Locks native Hugh Montgomery and the other CIA and MI6 operatives (such as British MI6 agents Janet Chisholm and Greville Wynne) who had helped manage Penkovsky and were on the receiving end of his vital information. (See the 2021 movie The Courier starring Benedict Cumberbatch as Wynne.) In total, Penkovsky is estimated to have had 140 hours of interviews with American and British operatives, passed on 111 rolls of film, and more than 10,000 pages of intelligence reports!
It is no surprise that Oleg Penkovsky had a book written about him entitled The Spy Who Saved the World. Unfortunately, Penkovsky was arrested by the KGB on the day before JFK’s address to the nation concerning the missile crisis. He was beaten and tortured for weeks before he was found guilty of treason and executed in the spring of 1963. Interestingly and appropriately, Penkovsky’s CIA code name was “HERO.” Without American and British operatives such as Hugh Montgomery, however, the transfer of Penkovsky’s vital information that enabled the Kennedy administration to resolve the Cuban Missile Crisis peacefully would have never occurred.
