High-Flying Youth

Rising to the Challenge

In 1941, the United States entered World War II. Billings, now 18 years of age, volunteered for the Army Air Corps. He was assigned to the 825^th Bomb Squadron, part of the 484^th Bombardment Group, and flew bombing missions over Europe.

At a critical point of the war, the clandestine Office of Strategic Services (OSS) selected Billings to participate in Operation Greenup. This involved flying behind enemy lines so spies and other special operations forces could parachute in. History proved that Operation Greenup was a crucial part of the Allied victories in Europe.

By the time the war ended, Billings had flown 39 missions for the OSS. He earned the Distinguished Flying Cross for his service in the Army Air Corps. Decades later, he earned the Congressional Gold Medal for his key role in the OSS missions. Billings was often called a hero for his efforts, but he didn’t let the praise inflate his ego. “The spies and the special forces – they were the real heroes,” he said.

From Commercial Flights...

In 1947, Billings received news from the government. The Army Air Corps had become the U.S. Air Force. With the new name came a new uniform. It was royal blue, and earned the nickname of “blue uniform.” Billings could not afford the blue uniform, and had to resign his commission.

Even though his military aviation career ended, Billings couldn’t stay away from flying for long. From 1946 to 1948, Billings worked as a flight and ground instructor at Hanscom Field (BED) in Bedford, Massachusetts. He soon became a commercial airline pilot - first for TWA, then for Eastern Air Lines. His career with Eastern Air Lines lasted 35 years, until he reached the mandatory retirement age.

...To Angel Flights

In 2015, Billings signed up to be a volunteer pilot for Angel Flight Mid-Atlantic (a program of Mercy Medical Angels). He flew patients to and from critical medical care in his Cessna. One of his friends, Nevin Showman, joined Billings in the cockpit. As friends and fellow aviators, Billings and Showman shared an inside joke: they preferred to call themselves “flying partners” rather than “co-pilots.”

Shortly after joining Angel Flight Mid-Atlantic, Billings embarked on the “Wings Around America” mission. This mission raised awareness for the nonprofit they flew for. They flew to all four corners of the continental United States. One stop was Victorville, California, where Billings flew B-24 bombers more than 70 years prior.

Billings flew more than 450 missions as one of more than 400 volunteer pilots who donate their time and resources to help patients who otherwise couldn’t access medical care. “I get paid in hugs,” said Billings.

Surprise of a Lifetime

In 2018, Angel Flight Mid-Atlantic hosted a celebration called Volunteer Pilot Appreciation Day (Pilot Day for short). Billings and Showman had flown the most missions out of all the volunteer pilots the year prior, and shared the Pilot of the Year Award for 2018.

This was not the only award for Billings. Frank Borman, an Apollo 8 astronaut and former executive for Eastern Air Lines, had written a special letter to Billings. Billings also earned a challenge coin from the U.S. Air Force Chief of Staff.

But the biggest award was yet to come. Angel Flight Mid-Atlantic's Executive Director at the time, Robb Alpaugh, had managed to track down an authentic “blue uniform” – complete with the awards Billings had earned from that time. It was truly the surprise of a lifetime!



Still in the Air

Billings recently turned 98 years old. Because of health issues, he had to retire from his role as a volunteer pilot. His decades of service did not go unnoticed. At a ceremony in November 2021, Billings received the Presidential Lifetime Achievement Award. Billings said that even though he wouldn’t sit at the controls, he would still be in the cockpit.



Mercy Medical Angels celebrates volunteer pilots like Billings, who have been the backbone of our mission for 50 years. Thanks to them, we’re still in the air.