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Mr. Waugh, a well-known, colorful and blunt-spoken figure in the intelligence community, was a Special Forces veteran by the time he first arrived in Laos in 1961, in the early days of the Vietnam War, as part of a United States military advisory mission called White Star.
Over parts of a decade in Southeast Asia, he helped train counterinsurgency forces in South Vietnam and Laos. He participated in parachute drops to the Ho Chi Minh Trail, which required jumping from aircraft at altitudes of 20,000 feet or more, he said, free-falling in the nighttime to the lowest possible height before popping the chute, to avoid enemy detection.
And he served with the innocuously named Studies and Observations Group of the Military Assistance Command, Vietnam, a clandestine unit that ran reconnaissance and rescue missions in South and North Vietnam, Laos and Cambodia.
“There was no rest at SOG, only war recon, rescue, sleep,” Mr. Waugh told Annie Jacobsen in her 2019 book, “Surprise, Kill, Vanish: The Secret History of C.I.A. Paramilitary Armies, Operators and Assassins.”
In June 1965, Mr. Waugh, then a master sergeant, was nearly killed when his team was overwhelmed by North Vietnamese forces in Binh Dinh Province, along the South Vietnam coast. He was shot in the knee, foot, ankle and forehead in a rice paddy. Thinking he was dead, North Vietnamese forces stripped him naked.
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