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While attending Joplin High School, Cummings was taught to fly by his godfather, Orville Wright, the aviation pioneer. Wise and Wilderson. His first solo was on March 3, 1927. Greeenwood Flying  During high school, Cummings gave Joplin residents rides in his aircraft for $5 per person. Christensen Mo Bio

While attending Joplin High School, Cummings learned to fly. Some reports of his learning to fly allude to a relationship with Orville Wright, the aviation pioneer, as being his god-father and his flight instructor. These reports appear to be based solely upon media interviews or reports of such interviews of Cummings. There is no historical record of Orville Wright having traveled to Joplin, Missouri, either around the time of the gestation or the birth of Robert Cummings, or during 1927 – the year Cummings learned to fly. Mr. Cummings, born in 1910, would have only been 8 years old when Orville Wright had essentially stopped flying as a result of injuries he sustained from an accident at Fort Myer, Virginia, in September 1908. That Orville Wright taught Cummings to fly is also contradicted by Cummings’ interview reported in the March 1960 Flying magazine. There, Cummings described that he learned to fly “by trial and error, mostly error” during 3 hours of instruction from a Joplin, Missouri plumber named Cooper before he soloed on March 3, 1927. p. 46-47. Cummings gave Joplin residents rides in his aircraft for $5 per person.