The Swashbuckling Lawyer Who Was the Ultimate Spy

William J. “Wild Bill” Donovan CC 1905, LAW 1907, was the head of WWII’s Office of Strategic Services (OSS), the predecessor to the Central Intelligence Agency. 

William J. “Wild Bill” Donovan CC 1905, LAW 1907

He was the ace of agents — architect of covert operations, recruiter of undercover assets, manipulator of disinformation, gatherer of priceless intelligence, perpetrator of psychological warfare, the all-seeing man in the shadows.

This was William J. “Wild Bill” Donovan CC 1905, LAW 1907, the head of WWII’s Office of Strategic Services (OSS), the predecessor to the Central Intelligence Agency. More than anyone else, Donovan laid the groundwork for this country’s vast present intelligence network. He was, by Dwight D. Eisenhower’s sights, “The Last Hero.”

A native of Buffalo, N.Y., Donovan cut an all-around Columbia figure — Phi Kappa Psi, the George William Curtis Medal for Public Speaking, track, crew and, finally, Lions quarterback. Although he graduated from the Law School (FDR was a classmate and admirer), he harbored a passion for bravado and derring-do. So in 1912 he joined some genteel Buffalo types (the “Silk Stocking Boys”) who, with official War Department permission, were organizing a local division of the New York National Guard. Ultimately they chased Mexican revolutionary Pancho Villa from late 1916 to early 1917. Soon after his return, with the Great War raging, Donovan won command of New York’s famed “Fighting Irish” 69th Infantry Regiment.

In France, where he was wounded three times, Donovan — by then a major —earned his “Wild Bill” rep. After a disastrous encounter at the Ourcq River in July 1918, in which he lost 600 of his 1,000 men (among them Sgt. Alfred Joyce Kilmer CC 1908, of “Trees” fame), he showed considerable élan at that September’s furious St.-Mihiel offensive. “Get moving; what do you think this is, a wake?” he bellowed.

At the Second Battle of the Marne, he went into combat wearing his decorations and insignia, as if daring the Germans to target him. “They can’t hit me and they won’t hit you!” he shouted. Though shot in the knee, attacked by gas and showered with the shreds of three of his men, he threatened to court-martial anyone who tried to get him off the field. For his actions, Donovan received the Medal of Honor. As Erasmus wrote — and as Donovan once jotted down — “Fortune favors the audacious.”

Come the Armistice, Donovan oscillated between his Wall Street law firm and public service. He was the U.S. attorney for the Western District of New York, assistant to AG Harlan Fiske Stone and a 1932 New York gubernatorial candidate. But his attention was increasingly focused on the new war in Europe. As it was, FDR was determined to help the British, but he wanted inside information about their ability to fight. Happily, the British foreign intelligence service, MI6, was eager to supply it. And so, in a series of discreet fact-finding missions, FDR dispatched Donovan to various war theaters to evaluate Axis and British capabilities and convey his impressions.

A certain Royal Navy officer, future James Bond creator Ian Fleming, helped plant a particular idea in Donovan’s head: Why not create some kind of integrated U.S. intelligence apparatus? Donovan agreed: “Modern war operates on more fronts than battle fronts.” He prevailed upon FDR, who on June 18, 1941, authorized an Office of Coordinator of Information, with Donovan as director.

Donovan turned the COI (it became the OSS in 1942) into a formidable enterprise. By 1943, its budget stood at $35 million; by the end of 1944, it employed 16,000 people. Many were bona fide commando types, penetrating enemy lines to stage raids, destroy installations and commit miscellaneous mayhem. Others were analysts, decoders, snoops, thieves, paymasters, safecrackers and cartographers. Donovan’s ranks eventually embraced such luminaries as John Ford, Sterling Hayden, Stephen Vincent Benét, Marlene Dietrich, Archibald MacLeish, Julia Child and Carl Gustav Jung, leading some to joke that “OSS” stood for “Oh, So Social!” So seriously did it take its clandestine purpose that others thought it an acronym for “Oh, Shush, Shush.”

“Strategy, without information on which it can rely, is helpless,” was one of Donovan’s mantras. He won his greatest acclaim through bold tactical operations. In May 1942 his agents burglarized the Lisbon office of the Japanese military attaché and stole his most secret cipher. In conjunction with the Army Air Forces, the OSS attacked 525 of 868 rail targets in France shortly after D-Day, causing massive logistical foul-ups.

Come war’s end, Donovan assumed that the OSS would continue, with he as its leader. But he had stepped on too many bureaucratic toes and made too many enemies. More important, many feared that a peacetime OSS would constitute an “American Gestapo.” The upshot was that the OSS was dissolved on September 20, 1945, with Donovan retiring as a major general.

Being honored with the College’s Alexander Hamilton Medal in 1950 and being appointed Ambassador to Thailand in 1953 did little to lift Donovan’s spirits. Hospitalized for dementia two years before his death in 1959, he “imagined he saw the Red Army coming over the 59th Street bridge, into Manhattan, and in one memorable last mission, fled the hospital, wandering down the street in his pajamas.” But his legacy is secure. Today, he is immortalized with a life-size bronze statue at the CIA’s Langley, Va., headquarters.

Another memorial, more abstract yet more personal, can be found on Columbia’s Amsterdam Avenue sky bridge. Tightrope Walker features two spindly figures, one perched precariously atop the other’s shoulders. Dedicated to Donovan by his friends and associates, its daring poise captures what he once told Corey Ford CC 1923: “It isn’t how brave you were yesterday, it’s how brave you are today.”