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  • The late Hugh Montgomery, a former ambassador who retired from the CIA in 2014 after serving the intelligence community for more than six decades, displays photographs from his younger days.
     The late Hugh Montgomery, a former ambassador who retired from the CIA in 2014 after serving the intelligence community for more than six decades, displays photographs from his younger days.

Intelligence Threats Increase in Complexity

The Cyber Edge
May 1, 2017
By George I. Seffers
E-mail About the Author

A CIA founding father warned that other nations will suffer insider leaks.

Editor’s note: Hugh Montgomery, the focus of this article, passed away April 6, just weeks after this SIGNAL interview.

It is just a matter of time before other countries face insider leaks similar to those that have haunted the American intelligence community, said Hugh Montgomery, a former U.S. diplomat and a pioneering intelligence officer who served for more than six decades.

Montgomery, a spy in the CIA’s early days who is considered a founding father of the agency, listed cyber as one of the intelligence community’s top threats. His assessment came on the heels of accusations of insider leaks at the National Security Agency (NSA) and the CIA. “I think they face a huge challenge in the whole cyber world. There is, as both NSA and now CIA have learned, a huge security issue facing them,” said Montgomery, who retired from the CIA in 2014 at age 90. “Clearly, the cyber world has introduced a new dimension of technical vulnerability that no one knows how to cope with.” 

The World War II combat veteran also warned that intelligence agencies from other countries likely will face the same threat in the future. “What’s going to be the next country that encounters the same difficulties? There will be others, I can assure you,” he cautioned.

Montgomery, who was honored posthumously last month with the AFCEA Charlie Allen Award for Distinguished Intelligence Service, said he stayed in touch with his intelligence community colleagues and that their reactions to the leaks were “unprintable.” He described the entire situation as “a mess” and “very discouraging.”

Edward Snowden, who leaked vast numbers of NSA documents to WikiLeaks, was a contractor for the agency, and some reports suggest the recent leaks of CIA data also may have come from contractors. Montgomery questioned whether too many contractors have too much access. “It’s one of the things Mr. Trump and his staff will have to consider because ... if the material came from contractors, then there’s obviously something wrong with contractors,” he said. “What a horrible business. I don’t understand it. I do not pretend to understand how this has happened. If it’s coming from inside, as I guess it is, they have a real problem.”

The leaks undoubtedly will affect international relations, but it is too early to tell exactly how, Montgomery offered. They also may exacerbate the intelligence community’s struggle to hire top technical talent, who can earn more working for industry, he said.

The 93-year-old admitted that the cyber world confounded him. “When I see all these numbers and letters jumping around the screen, I just turn off the machine,” he stated.

When asked about other threats facing the intelligence community, he responded: “Just look at a map—Russia, China, North Korea. You can look at the whole world while you’re at it.” And when asked if he can offer recommendations for the intelligence community, he simply said, “Good luck.”

The world, he said, has grown much more complex since the inception of the CIA. “There are more challenges than we can even begin to count. The world is far more complicated than in the ‘good old days’ of World War II,” he said with a hint of sarcasm.

Montgomery enlisted in the Army at age 18 and was wounded while serving as a paratrooper—he jumped into Normandy on D-Day with the 82nd Airborne. He subsequently joined the Office of Strategic Services (OSS), the CIA’s predecessor. The office was established in 1942 when Franklin D. Roosevelt was president. Maj. Gen. William Donovan, considered the father of American centralized intelligence, led the organization. “Because of his very close relationship with President Roosevelt, he was able to do things with 13,000 people that we couldn’t do with 13 million these days,” Montgomery declared. 

He recalled that Donovan, nicknamed “Wild Bill,” also enjoyed support from Gen. George Marshall, USA, who served as Army chief of staff under Roosevelt and “who came to appreciate the intelligence products he was getting from the OSS analytical branch,” Montgomery said.

The OSS was a small but capable organization. “It was able to create all kinds of irregular warfare activities in Europe and the Middle East and everywhere else, but again, simply because Donovan had a blank check from President Roosevelt,” Montgomery stated. 

When Roosevelt died in April 1945, Gen. Donovan sent a message to the OSS staff members saying the president’s death likely would mark the end of the organization because “I have more enemies in Washington than I do in all of Europe,” Montgomery recalled Donovan’s message saying. President Harry S Truman “didn’t waste very much time in, simply with an executive order, abolishing OSS. And that was the end of that,” he added.

OSS personnel scattered across government, but then, “Truman came to recognize in very short order that he needed an intelligence service, which led to the CIA,” Montgomery said. The CIA was created in 1947 when Truman signed the National Security Act into law.

Montgomery’s early days with the intelligence community involved moving behind enemy lines for a variety of missions, including the search for nuclear scientists. “We went in very small teams, and most or all of the team spoke fluent German. We had very carefully plotted and planned activities. They were just quick trips, normally using captured German vehicles and that sort of thing—sometimes successful, sometimes not,” he said.

Montgomery said he deliberately forgot the names of the scientists on their list because that is what intelligence operatives do. Most of those names, he added, would probably not be recognizable outside of nuclear science circles anyway. “To us, they were just names of scientists deep, deep inside Germany,” he said.

He also recalled helping a top-ranking German general escape from the former Czechoslovakia so that the officer could surrender to the United States rather than Russia. “We were able to get him in Prague during the last days of the confusion of the war and bring him out under a blanket in the back [seat] of a car to the demarcation line, which was west of Prague,” Montgomery revealed. “We brought him out, and he was turned over as a major war criminal and tried and inevitably hanged by the Czechs.”

Montgomery spoke several languages, including German, French, Spanish, Portuguese, Italian, Russian and Dutch, with “some Greek and a little Japanese here and there.” His mother was a language teacher, and he himself briefly taught Spanish and Portuguese at Harvard before being coaxed by friends to join the OSS and “earn an honest living back in Washington,” he recounted. Montgomery lost count of the number of countries he was assigned to during his career, but they included France, Germany, the former Czechoslovakia, Denmark, Russia, Italy and Greece, with some time spent in Holland as well.

As far as Montgomery knew, his life was never in real danger during the wartime missions. “I hope not. I never lingered long enough to find out. We believed in moving fast,” he said.

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