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The History-Maker: Remembering Ambassador Montgomery

Ambassador Hugh Montgomery was one of the greatest icons of the intelligence profession and one of the greatest American heroes of our time. From OSS commando, to legendary Cold War case officer, to US Ambassador, it’s hard to imagine a more storied or accomplished career than Hugh Montgomery’s—for an intelligence professional or for anyone else:

  • As an OSS commando in World War II, Hugh parachuted into Normandy ahead of the Allied invasion force.
  • As one of the first Americans to enter the Buchenwald concentration camp, he saw newly liberated inmates tear down a black SS banner and present it to him in gratitude for their freedom.
  • Below the streets of postwar Berlin, Hugh worked with the legendary Bill Harvey in supervising the construction of a tunnel that tapped into Soviet and East German communication lines, yielding an enormous trove of East Bloc messages.
  • While in Moscow, he helped handle Colonel Oleg Penkovsky, the source of pivotal information during both the Berlin and Cuban Missile crises.
  • And as a Deputy Ambassador to the United Nations in the late 1980s, Hugh countered Soviet exploitation of the UN Secretariat, particularly Moscow’s efforts to disseminate propaganda and conduct espionage in the United States.

Hugh was one of our nation’s silent warriors, carrying on the OSS ethos of consummate skill, remarkable bravery, and quiet humility. He was present for the entire modern history of American intelligence, from its origins in the wartime Office of Strategic Services (OSS) to the creation of the CIA. His story is woven into the very fabric of this Agency.

The recent passing of Hugh Montgomery has left a profound impact on the Agency; for those who knew and worked with him personally, and for those who have only known him through legend.

In memory of the man who was literally the epitome of the fabled ideal OSS recruit – “a Ph.D who can win a bar fight” – we’d like to share with you some of the exploits of the legendary Ambassador Montgomery.

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A young Hugh Montgomery
The Glorious Amateurs:

Hugh Montgomery had been studying at Harvard University to become a professor of languages—his mother’s profession—when WWII broke out. He left Harvard to join the Army in 1942.

Hugh’s command of German helped him become one of General William “Wild Bill” Donovan’s “Glorious Amateurs” – a phrase Donovan used to describe his fellow OSS officers. Hugh used his language ability to excellent advantage in Germany and Austria by claiming to be the son of German parents who had emigrated to South America—a cover story supported by his fluent Spanish.

Once, while hunting down war criminals, Hugh was given the name and address of a German baron and senior Nazi official in Munich. A butler answered the door to find a couple of grungy GIs and told them the baron was not receiving visitors.

“I do hate to interfere with the baron’s schedule,” Hugh replied in perfect German, “but the baron will receive us now.” Moments later, the baron was in the back of Hugh’s Jeep en route to being locked up.

From Spy to Scholar to Spy:

After the war, Hugh’s OSS supervisor, Richard Helms (who would later become DCI), urged him to join the newly established CIA. Hugh decided instead to go back to Harvard and finish his language degrees on the GI Bill. With fluency in eight languages and a working knowledge in several more, he earned his Bachelor’s magna cum laude, along with a Master’s and PhD, before joining the Harvard faculty.

Hugh eventually followed Helms’ advice, entering on duty at the Agency in January 1953.

Ambassador Montgomery would spend 24 years of his 50+ year Agency career overseas. He served as Chief of Station and Deputy Chief of Station in several Eastern and Western European countries. But his first six years as a CIA officer were in Berlin before the Wall went up—a city wide open for espionage and the perfect proving ground for a young case officer.

The Berlin Tunnel:

During the Cold War, monitoring and thwarting the Soviet Union’s influence worldwide was the top priority of the CIA. Berlin stood on the front lines of the superpower conflict. The East German capital was the center of a communications network connecting key European nodes and extending well into Russia. Soviet telephone and telegraph communications between Moscow, Warsaw, and Bucharest were routed through the city.

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Excavating Berlin Tunnel
By the early 1950s the Soviets had shifted from radio to land line telephones for most military traffic, transmitting both encrypted messages and nonsecure voice communications. CIA assessed that tapping the underground cables could be done securely and with little notice. Thus the Berlin Tunnel operation (aka Operation Gold) was born.

Hugh was not immediately read into the Berlin Tunnel operation, but was told by CIA Base Chief Bill Harvey to find sources with knowledge of the East German landline system. Along with maverick case officer Walter O’Brien, Hugh assembled a network of assets that reached deep into the Ministry of Post and Telecommunications. Without those crucial sources, there would have been no tunnel.

Once the tunnel was built and the tap installed, Hugh’s job was to take delivery of the tapes used to record the intercepts and ship them to Washington for exploitation. The Berlin Tunnel operation would last nearly a year before the Soviets shut it down in April 1956.

During that time, CIA and our British partners were able to record 50,000 reels of intercepts covering some 450,000 conversations. Translators worked full-time on transcribing the recordings into English until 1958—a landmark accomplishment made possible by Hugh and a small team of exceptional intelligence officers.

The Powder-Room Caper:

Hugh’s remarkable success in Berlin led to his appointment as Deputy Chief of Station in Eastern Europe, when tensions with the Soviet Union were at their highest. Hugh quickly mastered the elaborate tradecraft methods required to operate in hostile Cold War environments. Personal contact with assets was virtually impossible. Dead drops were essential.

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Oleg Penkovsky

It was during this time that Hugh was involved in a caper involving one of the most valuable assets in Agency history: Soviet GRU Colonel Oleg Penkovsky.

The US Ambassador threw a Fourth of July party at his residence, and Hugh was invited. He wasn’t there to mingle, however. Penkovsky planned to leave a package for Hugh during the celebration. The only catch: Hundreds of Soviets would also be in attendance.

The plan was for Penkovsky to leave the package inside the wall of a toilet’s flush tank at the residence for Hugh to retrieve. Simple, quick, and efficient. Except things didn’t go so smoothly.

When Hugh entered the bathroom to get the package, he realized the tank wasn’t a traditional, modern toilet, but rather an old-fashioned, European tank that was affixed high up on the wall and not easily reachable. With few options, Hugh decided to climb up on the wooden toilet seat to try and reach inside the tank. He was barely tall enough, but was able to stick his hand inside. Suddenly, there was a terrible cracking noise as the seat broke and splintered beneath him. Hugh quickly felt around for the package, but it wasn’t there. It had slid down to the bottom of the tank and he couldn’t reach it.

Unsure what to do now, Hugh eyed the sink, which clearly was not designed for people to climb on. It was his only option. Up he went, and sure enough, he could reach the tank. He felt around the bottom of the tank and found the package, but as he lifted his soaking wet arm, the sink upon which he was precariously balanced started coming away from the wall. He jumped down in a hurry and grabbed the sink before it crashed to the floor. Hugh managed to slip out of the bathroom without attracting attention. He found his wife, and they made a hasty retreat, dripping wet arm and all.

At the next Embassy staff meeting, the Ambassador said he wanted to know the name of the Russian S.O.B. who trashed his wife’s powder room.

During the Berlin Crisis of 1961, when Moscow issued an ultimatum to the Western powers to evacuate the city, Hugh received a report from Penkovsky advising that Khrushchev would back down if the Allies stood firm—which proved to be the case. Hugh personally translated and encrypted the entire message and sent it to the White House through CIA Director Allen Dulles. President Kennedy expressed his gratitude for Hugh’s work.

A Message from Italy:

Hugh’s mastery of clandestine tradecraft is certainly one of the elements that made him such an extraordinary officer, but it is only part of the story. Human intelligence is very much a social endeavor. Personality, character, and charisma help forge lasting relationships. Hugh made a lot of close friends over the years, including important figures whose personal ties could, on occasion, be of service to our country.

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Hugh Montgomery
In 1985, a plane carrying the terrorists who had hijacked the cruise ship Achille Lauro was forced by US fighters to land at a NATO airbase in Italy. A tense standoff ensued between Italian military police and US Special Forces over custody of the terrorists. Ultimately, the Italians apprehended the hijackers.

But Rome was upset over how the episode had been handled and wanted to convey a message to President Reagan through a mutually trusted and respected intermediary. Word went out that only one man would be allowed to receive it: Hugh Montgomery.

Flying by Concorde to Paris and then by Italian President Francesco Cossiga’s official plane to Rome, Hugh met with  Cossiga away from the limelight in an aide’s suburban apartment and was asked to write down a verbatim text of the message, which remains classified to this day. It was sent to Secretary of State Shultz, who relayed it to the White House. And yet again, Hugh earned the thanks of a grateful President.

Spy Against Spy:

Of course, not everyone Hugh encountered on the job became a close friend. While serving in Western Europe, he received a phone call from Philip Agee, the notorious Agency turncoat who exposed the identities of hundreds of our officers. Agee demanded to meet with him and threatened to “destroy” Hugh if he refused.

Hugh’s response was direct, succinct, and well within the capabilities of an OSS commando. “If I could get my hands on you,” he said, “I would gladly wring your neck, so I guess that makes us even.”

Mr. Ambassador:

In 1981—after serving as National Intelligence Officer for Western Europe and receiving the Distinguished Intelligence Medal from CIA Director Bill Casey—President Reagan appointed Hugh to direct State Department’s Bureau of Intelligence and Research.

Four years later, Hugh was given the rank of Ambassador—a rare honor for an Agency officer—and was asked by his friend and former Deputy Director of CIA, General Vernon Walters, to serve as his deputy at the United Nations. Hugh vastly improved intelligence support to the US Mission, establishing the close relationship that endures to this day.

As Hugh’s UN tour was coming to an end in 1989, so too was the Cold War. In December 1991—the very month the Soviet Union ceased to exist—CIA Director Bob Gates appointed Ambassador Montgomery to be his Special Assistant for Foreign Intelligence Relationships.

An important legacy of Hugh’s pioneering work was to set precedents for the sharing of US intelligence with UN agencies, especially war crimes tribunals. Having brought Nazis to justice some fifty years earlier, Hugh ensured that the international community had the information needed to indict those who committed atrocities during the violent breakup of Yugoslavia.

His efforts also laid the groundwork for the massive expansion of information sharing and joint operations with our foreign partners in the wake of the September 11th terrorist attacks.

A Legacy Like No Other:

After a lifetime in intelligence – serving under OSS Chief General “Wild Bill” Donovan and 20 CIA Directors – Hugh understood the Agency better than almost anyone. That’s why former CIA Director Michael Hayden chose Hugh to be the Director of the DCIA History Project in 2007. Hugh made profound contributions to the Agency’s historical record, drawing from his wide experience from the beaches of Normandy to a post-9/11 world.

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Amb. Hugh Montgomery receiving the Donovan Award from then-CIA Director Brennan, OSS Society Dinner, 2015.
In 2014, Hugh was awarded the Distinguished Career Intelligence Medal, the Director’s Award for Distinguished Service, and the Intelligence Community Seal Medallion. He retired from the CIA that spring, after 63 years of service.

Retired at the age of 90, Hugh spent his last years mentoring the younger generation of Intelligence officers. He also enjoyed reading, crossword puzzles and word jumbles, and acting as chairmanship of the OSS Society.

Hugh Montgomery passed away on April 6, 2017, after a brief illness. His beloved wife of 66 years, Annamarie, passed away a few years prior, but he is survived by his loving daughter and devoted son.

Ambassador Montgomery was a pioneering intelligence officer and a great American; one of the finest, most talented individuals to ever join the Clandestine Service. He faced risk and ambiguity with valor and purpose, always embodying the good faith and decency of the country he so proudly served.

We are exceptionally fortunate and honored to be heirs to the history that Hugh Montgomery made.


* Parts of this article were adapted from a speech former DCIA John Brennan gave at Hugh Montgomery’s retirement ceremony in 2012, as well as a speech Brennan gave at an OSS Society dinner honoring Ambassador Montgomery in 2015.


Posted: Jun 05, 2017 04:14 PM
Last Updated: Jun 14, 2017 01:45 PM