Harry B. Winger was born in August 1924 in Pulaski, Pennsylvania and grew up there on a farm. He joined the Army Air Corps at the age of seventeen and served as a pilot during World War II. He was shot down and remained a prisoner of war (POW) for eleven months and 23 days, being released when the war ended. He then used his skills and flew for MATS (Military Air Transport Service) for fourteen years. Winger began flying for the Maine Aviation Corporation in 1966, which is when he met Senator Muskie. He flew Senator Muskie around New England for several years, especially during campaigns.
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L'Hommedieu, Andrea, "Winger, Harry B. oral history interview" (2003). Edmund S. Muskie Oral History Collection. 413.