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Spy party: Tuxedos, martinis and some of the greatest heroes of World War II

Helias Doundoulakis, left, receives a Distinguished Service Award on Nov. 7 from Rear Adm. Brian Losey, the commander of Naval Special Warfare Command. (Photo courtesy the OSS Society)
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Army Maj. Frank A. Gleason’s small unit was facing an advancing Japanese army in China in December 1944 when he made a judgment call: Rather than let 50,000 tons of ammunition and weapons fall into enemy hands, they’d blow it all up.

The fiery chain reaction of explosions, Gleason recalled, went on for three days. It was a highlight of a long deployment in which Gleason’s unit detonated more than 150 bridges and an assortment of river ferries, locomotives, barracks and weapons stockpiles during one of the great sabotage missions of the World War II.

“People have asked me, ‘Weren’t you afraid?’ And I say, ‘I didn’t know enough to be afraid,'” said Gleason, 95. “We just had a great time just blowing up everything. I only had one objective, and that was if the Japanese could use it, I tried to destroy it.”

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Gleason, who retired as a colonel, was one of several veterans of the secretive Office of Strategic Services (OSS) who were recognized Saturday for their heroism at a black-tie dinner in Washington. A precursor of the CIA, the organization carried out everything from propaganda missions to espionage behind enemy lines in both the European and Pacific theaters during World War II.

The annual dinner was hosted by The OSS Society, which counts some of America’s best-known modern spies and special operators among its ranks. Those in attendance Saturday included CIA director John O. Brennan, former Undersecretary of Defense for Intelligence Michael Vickers, former U.S. Special Operations Command chief Adm. Eric T. Olson and Rear Adm. Brian L. Losey, the chief of Naval Special Warfare Command.

The event’s stars, however, are the nonagenarian veterans of the OSS, who were sprinkled at tables throughout the Ritz-Carlton banquet hall as officials offered nearly a dozen toasts with martinis (never champagne). Gleason received a Distinguished Service Award, along with George and Helias Doundoulakis, a pair of Greek-American brothers who served in Greece under cover while spying on the Nazis.

The event’s biggest recognition — the William D. Donovan Award — went to Amb. Hugh Montgomery, who was wounded while serving as a paratrooper in World War II and joined the OSS’s counterintelligence branch, known as X-2. He went on to become one of the CIA’s founding fathers, and served in several other roles in the intelligence community before retiring in 2014. The award he received is named after the two-star Army general who led the OSS.

This video was shown at the dinner to explain Montgomery’s selection:

Montgomery, who turns 92 this month, recalled Saturday that he didn’t know what X-2 was during World War II. His unit was known at the time only as the 12th Army Group’s Special Counterintelligence Attachment. It worked frequently with MI6, the legendary British military intelligence organization, and its members had wide latitude to move throughout Europe.

To explain the secretive nature of operations at the time, Montgomery recalled that some members of his unit were given what was known as the “Eisenhower Pass,” a document that was signed by Gen. Dwight Eisenhower, the supreme commander of Allied Forces in Europe. It included little more than his signature, a phone number and directions in several languages for anyone reading the document to call the number if a soldier was detained.

“When this document was issued, we were told that without fail, it had to be returned intact if the war ever ended, or we would never see the U.S.A. again,” Montgomery said. “Needless to say, we took great care of this treasure and used it sparingly, although it did serve us well when the need arose.”

The OSS Society continues to press for recognition for the remaining OSS veterans, said its president, Charles Pinck. Last week, legislation was introduced on Capitol Hill to have them recognized with the Congressional Gold Medal, one of the top awards a civilian can receive.

The Gold Medal has been used to recognize groups of military veterans in the past, including the Native American Code Talkers of World War I and World War II, black U.S. Marines who were trained for war at Montford Point, N.C., and the Monuments Men, who served during World War II to protect art and artifacts from destruction.