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To Washington society matrons, Doole seemed the very image of discreet old money. In fact, he grew up poor, of strict and frugal Lutheran parents, on a 160-acre hog and chicken farm in Liberty. He went to aggie school at the University of Illinois, where he kept to himself. "We were not real buddy- buddy," says his sister Mildred Nation. "We minded our own business." Winning a commission in the Army in 1931, Doole learned how to fly airplanes. He later became a pilot for Pan Am, at first flying old Ford Tri-motors on the Guatemala-to-Panama run. Along about 1953--no one seems quite sure when --Doole made an unusual career move. He went to work for the Central Intelligence Agency.
Officially, the CIA says it has no record that Doole ever worked there, but among old agency hands, he is a legend. Operating out of a small, nondescript office on Connecticut Avenue, he founded and ran a far-flung network of airlines that the agency used to carry out its covert operations all over the world. Owned by a holding company, the Pacific Corp., that was itself a CIA front, Doole's empire included Air America, Civil Air Transport, Southern Air Transport, Air Asia and dozens of small puddle-jumper lines. Together, at their peak in the mid '60s, these CIA "proprietaries" added up to an airline that was almost the size of TWA, employing nearly 20,000 people (as many as the CIA itself) and operating some 200 planes. Even the CIA was not sure just how many. Asked by then Deputy Director Helms to account for all the planes in Doole's regime, a staffer spent three months on the project before confessing that he could never be more than 90% certain. The problem, explained the exasperated staffer, was that Doole was forever leasing planes between his shell corporations and changing their markings and tail numbers.
Traveling around the world, orchestrating his vast air armada, Doole kept his airplanes busy. Under the cover of legitimate freight and charter services, Doole's airlines supplied a 30,000-man secret army in the mountains of Laos for a ten-year war against the Pathet Lao, dropped scores of agents into Red China, and helped stage an unsuccessful revolt in Indonesia. Not surprisingly, all this flying about aroused curiosity. In 1970 a New York Times reporter asked Doole if Air America had any connection with the CIA. "If 'someone out there' is behind all this," Doole airily replied, "we don't know about it."
Doole's pilots, who flew in and out of tiny jungle fields in abysmal weather and sometimes under enemy fire, were a raffish lot. They referred to the CIA as "the customer," the ammunition they dropped as "hard rice" and being under heavy fire as "sporty." Brushes with death were described as "fascinating." To be "absolutely fascinated" meant scared witless.
Doole would appear from time to time at CIA bases from Vientiane to Panama City, but he stayed aloof from the pilots, many of whom regarded him as a bit of a snob. "I never saw the man without a tie on," scoffs one. Doole played bridge, flew airplanes and did business deals the same way: slowly and deliberately. "The Chinese liked to negotiate with him," recalls a former CIA official. "He was polite; he never showed any excitement. But he was tough."