Post was born in Grand Saline, Texas (Van Zandt County), to farmer parents William Francis and Mae Quinlan Post, but his family moved to Oklahoma when he was five. His aviation career began at age 26 as a parachutist for a flying circus, Burrell Tibbs and His Texas Topnotch Fliers, and he became well known on the barnstorming circuit. On October 1, 1926, an oil field accident cost him his left eye, but he used the settlement money to buy his first aircraft. Around this time, he met fellow Oklahoman Will Rogers when he flew Rogers to a rodeo, and the two eventually became close friends. Post was the personal pilot of wealthy Oklahoma oilmen Powell Briscoe and F.C. Hall in 1930 when Hall bought a high-wing, single-engine Lockheed Vega, one of the most famous record-breaking aircraft of the early 1930s. The oilman nicknamed it, the Winnie Mae, after his daughter, and Post achieved his first national prominence in it by winning the National Air Race Derby, from Los Angeles to Chicago. The fuselage was inscribed, "Los Angeles to Chicago 9 hrs. 8 min. 2 sec. August 27, 1930." Adam Charles Williams finished second with a time of 9 hrs. 9 min. 4 sec.
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