How the OSS Shaped the CIA and American Special Ops


Wild Bill Donovan’s admirers and critics still argue over his legacy, but on one point they agree: His World War II Office of Strategic Service (OSS) became the Petri dish for the spies who later ran the CIA as well as the special operators who conduct some of the most daring raids the world has ever seen.

Four CIA directors — Allen Dulles, Richard Helms, William Colby and William Casey — learned the craft of clandestine warfare as operatives for Donovan’s OSS. Indeed, the daring, the risk-taking, the unconventional thinking, and the élan and esprit de corps of the OSS permeated the new agency.

So would the OSS’s failings: the delusions that covert operations, like magic bullets, could produce spectacular results, or that legal or ethical corners could be cut for a higher cause. Dulles launched the calamitous operation to land CIA-trained, anti-Castro guerrillas at Cuba’s Bay of Pigs. Helms was convicted of lying to Congress about the CIA’s effort to oust President Salvador Allende in Chile. Colby would become a pariah among the agency’s old hands for releasing to Congress what became known as the “Family Jewels” report on CIA misdeeds during the 1950s, ‘60s, and early ‘70s. Casey would nearly bring down the CIA — and Ronald Reagan’s presidency — from the scheme to secretly supply Nicaragua’s Contras with money raked off from the sale of arms to Iran in exchange for American hostages in Beirut.

Few appreciate how remarkable it was that President Franklin Roosevelt appointed William J. “Wild Bill” Donovan, in July 1941, to be the head of an intelligence organization called the Coordinator of Information, later renamed the Office of Strategic Services. Donovan was a Republican, Roosevelt was a Democrat, and the two had a history of fierce political battles in New York. But to Roosevelt, Donovan — a hero of the Great War and part of the Republican Party’s internationalist wing — was the only one who seemed to be thinking seriously about how to set up a worldwide foreign intelligence service, which FDR desperately needed as the cyclone of World War II approached the United States.

Donovan started with just one man — himself. By the end of the war, he had been promoted to major general and had assembled a force of more than 10,000 spies, saboteurs, commandos, propagandists, research analysts, and support personnel operating in stations all over the world. He had clandestine officers who stole secrets from the Axis, guerrillas who fought behind enemy lines, some of the country’s finest minds analyzing the intelligence, and psychological warfare specialists who tried to sap enemy morale.

Based in Switzerland, Dulles ran the OSS’s most successful spy operation against the Third Reich. Casey organized dangerous missions to penetrate Nazi Germany. Colby led daring commando raids into occupied France and Norway. Helms mounted risky intelligence programs against the Russians in war-torn Berlin just after the German surrender.

After FDR died, President Harry Truman, who was not close to Donovan and had received derogatory reports on the OSS and its director, shut down the agency on October 1, 1945, and parceled out its functions to the Pentagon and State Department. Truman was not blind to the need for a foreign intelligence service to spy on future Cold War threats. He just didn’t want Donovan and his OSS leading it. In 1947, however, Truman created the Central Intelligence Agency, whose organization practically mirrored the postwar spy service Donovan had in mind and was staffed by a number of OSS alumni.

Dulles ran the CIA as he had his OSS station in Switzerland. He believed that intelligence was a key part of American foreign policy and that the network of associations, the breadth of vision and the daring he had displayed fighting the Nazis would succeed in battling communism. Spying during the war and afterwards was a gentleman’s pursuit, he believed, practiced in the shadows by and among “men of affairs” like him, who were comfortable bending ethics or cutting legal corners for a higher cause. Though he talked little about Donovan after the war, Dulles’s operating style mirrored the general’s in many ways. Like Donovan, Dulles showed no interest in managing the CIA’s inner workings, leaving them to his deputies so he could be free to dabble in the clandestine operations that interested him.

Helms, who took over the CIA in 1966, had no vision for recasting the agency as Dulles had. His strength, as it had been in postwar Berlin, was management, not innovation. He was also determined to keep the CIA out of the headlines, ordering division heads to scrub covert operations overseas for security and shut down the ones in danger of being exposed. Though Helms was a demanding taskmaster, subordinates groused that he was too soft on the “old boys club” of former OSS officers in the agency, which needed shaking up. Helms wanted to keep his distance from old World War II spy pals so he wouldn’t be seen as playing favorites as director, but play favorites he did. He pulled OSS officers’ children who had joined the CIA out of meetings to give them a special welcome in his seventh-floor office at Langley. He often balked at firing veterans who misbehaved overseas, instead finding out-of-the-way jobs for them in headquarters.

Colby, who liked to putter around his Bethesda, Maryland home wearing his floppy Army fatigue cap from World War II, was profoundly affected by his OSS experience, say friends and relatives. As Director of Central Intelligence he drove his own car to work, ate with employees in the cafeteria, called in young analysts to compliment them on their reports and suggest ways their work could be improved, and found time in his schedule to listen to any employee walking in with a complaint. Like Donovan, he believed the mundane work of information gathering often produced more valuable intelligence than a Mata Hari-style escapade. With advances in electronic intelligence gathering, the human spy was a “contributor, but not the sole actor,” he said.

Casey hung two photos on the wall of his seventh-floor office — portraits of Ronald Reagan and Wild Bill Donovan. He ran the CIA the way he thought the general would. Like Donovan, he kept his door open to all ideas for operations. He hated bureaucracy, circumvented the chain of command, and poked his head into offices rungs below. He was proud, as Donovan had been, of the vast array of PhDs working at Langley. Like Donovan, he loved to tour his overseas stations, not only to boost morale and size up field officers who worked for him but also to leave Washington’s political wars behind. When he returned, he always delivered vivid trip reports to President Reagan, just as Donovan had done with Roosevelt.

Today, a statue of Donovan, commissioned by Casey when he was Director of Central Intelligence, stands in the main foyer of the CIA’s headquarters building — a symbolic reminder that Donovan was the father of modern American espionage. The basic skills agency officers practice today differ little from those of their OSS predecessors, save for more modern technology.

The U.S. Special Operations Command (USSOCOM) also claims an OSS lineage. Donovan’s special operations teams, for example, supplied partisans with weapons to fight the Nazis in Yugoslavia. His Detachment 101 organized guerrilla attacks against Japanese military targets in Burma. The OSS also fielded more than a thousand highly trained, foreign language-speaking paratroopers, skilled in sabotage and small-arms tactics, who were used in small groups to harass the enemy. These Operational Group commandos, called OG’s, fought behind the lines in France and Italy. A glass-enclosed case, full of Donovan memorabilia, sits in the main foyer of USSOCOM’s Tampa, Florida headquarters. The command’s leaders have held brainstorming sessions to explore what this modern force can learn from its roots and how it can emulate the special operations fighters of the OSS.

Donovan can also be considered the father of the psychological operations USSOCOM and the CIA wage. In the OSS, these were called morale operations and the technology used was, in some cases, far cruder than the kind used in today’s dark arts. Donovan’s officers planted rumors in newspapers claiming that top Nazis were abandoning Germans and fleeing to South America, dropped leaflets on Wehrmacht soldiers, and beamed radio broadcasts at them with propaganda messages mixed with songs by Marlene Dietrich.

Clearly, Donovan was one of the men who shaped modern unconventional warfare. Today’s shadow warriors who practice espionage, launch covert attacks, or try to change hearts and minds overseas can trace their heritage back to the OSS and its band of “glorious amateurs.”


Douglas Waller is an author, lecturer, and former correspondent for Time magazine. He is the author of Disciples: The World War II Missions of the CIA Directors Who Fought for Wild Bill Donovan (Simon & Schuster) which will be released on October 6. He also wrote Wild Bill Donovan: The Spymaster Who Created the OSS and Modern American Espionage (2011), described by Booklist as “the definitive biography of a seminal figure in the history of American intelligence.”