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Billy Rees was born in Jonesboro, Arkansas, where he lived much of his life. He graduated from Arkansas State College with a B.S. degree and a private pilot's license. During World War II, he served in the U.S. Army Air Forces as a navigator and navigation instructor. He flew the "Hump" from India to China and then joined the Ferry Command in Long Beach Calif. He reached the rank of major.
After the war, Billy became a navigator for Seaboard. He claimed to have owned 2 nightclubs, 2 liquor stores, 2 restaurants, 1 theater, 1 pool hall, and a beer lounge; as well as 19 new Cadillacs, and 4 motorcycles.