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John Billings (1923–2022), WWII spy pilot

by Linnea Crowther

John Billings was a U.S. Army Air Forces veteran of World War II who flew Allied spies behind enemy lines for the Office of Strategic Services (OSS).

A lifetime of flight

Billings took his first flight on his third birthday and discovered a lifelong passion. He learned to fly as a teen, before enlisting in the U.S. Army in 1942 and undergoing aviation training. Once in the Army, Billings was recruited for Operation Greenup by the OSS, the precursor to the CIA. Billings’ part in the mission involved flying three Allied spies into the Austrian Alps, where they would gain important information about Nazi activities. It was a dangerous mission, one that other pilots refused to undertake, but Billings was up for it and successfully completed the flight. It was the first of 39 missions he would fly for the OSS during the war. Billings retired from the military as a captain in 1946. He was honored with a Distinguished Flying Cross.

After returning home from World War II, Billings became a commercial pilot, working for Eastern Airlines for decades before his retirement in 1983. He continued to fly as a volunteer for Mercy Medical Angels, which flies “Angel Flights” for patients who are unable to afford long-distance transportation for critical medical care. He piloted more than 400 flights for the organization, and in 2015, he flew around the perimeter of the U.S. to raise awareness of Mercy Medical Angels. Billings continued volunteering for Angel Flights well into his 90s.

Notable quote

“Everyone has some sort of addiction, and flying’s mine. But I have an excuse. I was born with a genetic defect. My feet hurt if I stand on the ground too long.” —from a 2015 interview for the Santa Cruz Sentinel

Tributes to John Billings

Full obituary: The Washington Post

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