The Germans stopped them cold, and a machine-gun bullet shattered Donovan’s knee. But he once again refused orders to evacuate, and spent the next five hours hobbling around and preparing his men for the inevitable German counterassault. When it came, he rallied the Fighting Irish and drove the Huns back into the fortress in a rout, all but winning the battle single-handedly. Had the assault failed, Donovan would have been court-martialed (assuming he even lived). As it was, he earned the Medal of Honor and returned home one of the most highly decorated soldiers in American history.

When World War II rolled around, Donovan was working in a New York law firm. He happened to have attended law school at Columbia with Franklin D. Roosevelt, and Roosevelt sent his old chum to England in July 1940 to provide a more accurate picture of events there than Joseph Kennedy Sr., the defeatist ambassador to the U.K., could. Although Donovan agreed that things were grim, he emphasized the grit of the British people and singled out Winston Churchill as a stupendous leader.* The assessment bucked up FDR’s spirits and contributed to the Churchill-Roosevelt alliance that would ultimately help defeat Hitler.

Read: That time the CIA bugged a cat to spy on the Soviets

Donovan parlayed his field trip to England into a job as Roosevelt’s coordinator of intelligence, and from there he founded OSS and became its chief. But while the role made sense on paper—Donovan clearly had the vision and drive to see OSS succeed—Wild Bill also lacked pretty much every other skill necessary to run a government agency. Even those who adored him admitted that he had “abysmal” if not “atrocious” administrative skills, and he simply didn’t have the patience or fortitude to manage people. As a result OSS became one of the most poorly run agencies in American history. Employees used to laugh over a line from Macbeth that perfectly summed up the enterprise: “Confusion now has made his masterpiece.”

Nowhere were Donovan’s flaws more evident than in his hiring practices. Needing to throw together an agency quickly, he turned to his circle of friends in New York and hired blue bloods by the dozen. The OSS roster was lousy with Mellons, Du Ponts, Morgans, and Vanderbilts. Columnists joked that the agency’s initials actually stood for “Oh So Social.” In Donovan’s defense, hiring aristocrats did make sense on some level: They usually spoke several languages and knew Europe well. But holidays on the Riviera were a far cry from war. As one reporter noted, “Knowing how to speak French in a tux didn’t necessarily prepare recruits for parachuting into enemy territory or blowing up bridges.” More than a few heirs and heiresses suffered “dramatic mental crackups” in the field.

Even more than aristocrats, however, Donovan loved misfits, and he staffed OSS with a bizarre array of talent. There were mafia contract killers and theology professors. There were bartenders, anthropologists, and pro wrestlers. There were orthodontists, ornithologists, and felons on leave from federal penitentiaries. Marlene Dietrich, Julia Child, John Steinbeck, John Wayne, Leo Tolstoy’s grandson, and a Ringling circus heir all pitched in as well. Observers sometimes referred to OSS as “St. Elizabeths,” after the well-known Washington, D.C., lunatic asylum. One top official there admitted that “OSS may indeed have employed quite a few psychopathic characters.” Donovan once said, “I’d put Stalin on the OSS payroll if I thought it would help defeat Hitler.” No one knew whether he was kidding.