Inside the Party for America’s Finest Spies

At the annual gala which celebrates the Office of Strategic Services, the World War II espionage outfit that birthed the modern U.S. intelligence community, tales of derring-do were swapped humbly.

The OSS Society

John Brennan arrived at the cocktail party on Saturday night wearing a name tag—as if anyone in the room would have trouble recognizing him.

The Director of the Central Intelligence Agency, or “D/CIA,” as the plastic-sheathed card affixed to his tuxedo lapel announced him, navigated the reception room at the Ritz-Carlton in Washington, which was now packed elbow-to-elbow with spies and special forces.

Eric Olson, the retired admiral and former commander of U.S. Special Operations Command, and the first Navy SEAL ever to lead that elite group, spotted Brennan through the crowd and came over to shake his hand, as a photographer captured the moment.

Olson was wearing a name tag, too. Everyone was. Which was a little curious considering that many people in the room had been trained to appropriate a fictional identity and blend into a crowd. Advertising oneself is not exactly good spycraft.

But these fellow spooks and soldiers hardly needed to be reminded of who was whom.

Many of them had served together, in assignments from Berlin to Baghdad, and surely kept enough secrets among themselves to fill a hundred seasons of Homeland.

This annual gala, which celebrates the Office of Strategic Services (OSS), the World War II espionage outfit that birthed the modern U.S. intelligence community, has become the closest thing that America’s spies and secret warriors have to a prom.

The only bit of glitz missing is a red carpet, but something about that color in a room filled with aging Cold Warriors just wouldn’t do.

The spies in black tie mixed with military officers festooned in fruit salads of medals and ribbons and women in ball gowns, stopping here and there to greet an old friend.

Michael Vickers, the Pentagon’s former top intelligence official, stood in the middle of the room, the best vantage point to survey the whole of the terrain and a prime spot to meet and greet.

Tom Ridge, the ex-Pennsylvania governor and first secretary of Homeland Security, leaned into a conversation amidst the din of clinking glasses.

Gen. Norton Schwartz, who retired in 2012 as chief of staff of the Air Force and now runs a trade association/consulting group for former national security officials, sipped on a white wine as the increasingly excited crowd began snapping selfies.

Get The Beast In Your Inbox!

Daily Digest

Start and finish your day with the top stories from The Daily Beast.

Cheat Sheet

A speedy, smart summary of all the news you need to know (and nothing you don't).

By clicking “Subscribe,” you agree to have read the Terms of Use and Privacy Policy
Thank You!
You are now subscribed to the Daily Digest and Cheat Sheet. We will not share your email with anyone for any reason.

At least two former CIA directors moved through the stream of VIPs, which included a retired general who used to the Defense Intelligence Agency, a couple of congressmen, and the Colombian ambassador to the United States.

Packed as they were, the guests occasionally parted, making way for some stooped, wizened soul looking for a spot to rest, a highball glass in one hand and a cane in another.

These were the original members of the OSS, the so-called “glorious amateurs” hand-picked by the outfit’s founder, “Wild Bill” Donovan, to drop out of college and jump out of airplanes behind enemy lines in Europe and Asia.

They left the halls Yale or the tedium of office jobs and became saboteurs and commandos in a clandestine war against Germany and Japan.

Many of them had never left the United States in their short lives. Nearly all of them are in their 90s now, and every year, fewer of their tribe make it to the party.

If Donovan, as the CIA historians call him, is the Father of American Intelligence, these were his children.

To serve in the OSS was to take part in what even Donovan himself called “an experiment.”

No one could say for sure whether an organization composed of men and women chosen for their facility with languages and their perceived cunning, more than how they handled a rifle, would actually make a difference in the war.

They did, of course. And when the war was over, some of the amateurs went back to their comparatively normal lives. But others made a life out of espionage.

Among them was Amb. Hugh Montgomery, who would be receiving the night’s big honor, the Donovan Award, and who graciously, patiently, posed for photo after photo with adoring fans.

Montgomery may be the inheritor to Donovan’s legacy. When he finally retired from the CIA—in 2014—he was said to be the last original member of the OSS working full-time at the agency.

For the current generation of senior spies, Montgomery is the bridge to their origin story.

You can draw a line from him to a man like John Bennett, the former head of the National Clandestine Service and one of the most important spy masters of the War on Terror, who received a career achievement award on Saturday. The award, not surprisingly, is named after Montgomery.

Montgomery began his service in OSS’s X-2 unit, which ran counterintelligence operations during WWII and was so secret, he said, that even he didn’t know its name until years later.

X-2 was the only unit given information from the Ultra program, Britain’s effort to crack encrypted German communications.

In the Cold War, Montgomery served in Athens, Rome, Paris and Vienna. In Berlin, he helped tap Soviet communications lines running under the city. In Moscow, he ran one of the most famous and, some say, productive CIA assets in history, the Soviet officer Oleg Penkovsky.

After his days abroad, Montgomery became a consigliere at Langley, a walking repository of the agency’s history who, former Director Leon Panetta later said in a tribute video, knew the particulars of the agency’s relationships with foreign intelligence services better than anyone.

The crowd of several hundred heard all these stories, and more, because the annual gala is really a tribute, bordering on a valedictory. The cocktail reception gave way to toasts in the neighboring ballroom, one of the largest in Washington, where a seated three-course dinner would be served before the presentation of several awards.

It’s the tradition of the OSS Society, the gala’s host, to serve every guest a dry martini, in honor of the liberation of Paris, when, it is said, war correspondent Ernest Hemingway walked into the Ritz and ordered 73 of the cocktails, for himself, the OSS men he’d teamed up with, and a band of French partisans.

David Cohen, an old CIA hand who led the New York Police Department’s first intelligence unit after the Sept. 11 attacks, offered the first of 10 toasts, “to the United States of America.”

A parade of notables kept raising their glasses, to the commander-in-chief, to the OSS, to Donovan and his contemporaries who went on to run the CIA, to the U.S. Special Operations Forces.

It’s a testament to the OSS nonagenarians’ fortitude that they remained upright. Or perhaps gin is the secret to their longevity.

Finally there was a toast to “the ladies,” a hidebound tradition that overlooks the fact that plenty of women fought with the OSS, including Stephanie Rader, who served undercover at the U.S. embassy in Poland at the close of the war.

Rader was seated with about half a dozen close friends who buy a table at the dinner every year and have lately been trying to get her the Legion of Merit, an award she was nominated for seven decades ago but still hasn’t received.

The head of the OSS Society, Charles Pinck, offered Rader a special nod from the podium and noted she was celebrating her 100th birthday, which brought everyone in the ballroom to their feet. Rader, who has Parkinson’s disease, remained in her wheelchair amid the applause, and, with the help of a friend, raised her arm and seemed to make an ever-so-slight victorious fist.

During the course of the long evening—Brennan wished the room “good morning” when he rose to present the last award, to Montgomery—some of the glorious amateurs seemed mystified as to how they ended up in a ballroom filled with generations of trained professionals, and resisted taking too much credit for the “experiment” that paved their way, even as they were handed awards for distinguished service.

Helias Doundoulakis told the crowd that he’d had only six months of training before he was dropped into Nazi-occupied Greece to gather intelligence on German troop movements. He just did his part, he insisted. His brother, now dead, had been the better warrior.

Another awardee, Col. Frank Gleason, who as a young OSS officer became a whiz with explosives and bombed, by his own count, hundreds of Japanese targets, from bridges to train cars, shrugged off his derring-do. He was just a kid, he said. “I didn’t know enough to be afraid. We just had a great time blowing stuff up!”

This forced humility is a trademark of the Greatest Generation, and a frequent irritant for their children and grandchildren who want to know what their forebears actually did in the war.

But their reticence to linger too much on old stories was also a useful emotional bulwark in an evening that could easily have given way to weepy, maudlin displays of patriotism.

The amateurs know what they did, and they were happy for others to know it too. But they didn’t need speeches and awards.

The war may have been an adventure, but it was an ugly, perilous one, too.

Doundoulakis, who delighted the crowd with breathtaking tales about evading two Nazis in a bar in Thessaloniki and escaping with his life through a window before dashing off an important telegram to OSS headquarters, was reminded that many of his compatriots had no stories to tell.

More than a few had their covers blown, he said, and their bodies were later found with their fingers missing.

It was just the right dose of sobering reality to keep the revelers grounded without wrecking their night. Let’s remember, but not too much, Doundoulakis seemed to say. Better to laugh and not to cry.

They were, after all, just kids.