Ashby’s commercial aviation career began when he joined United Airlines as a flight operations instructor responsible for training new pilots on the Boeing 727, 737, and 747. United had no black pilots at the time according to Ashby’s obituary. In 1973 Robert Ashby joined Frontier Airlines as its first black pilot, eventually amassing over 22,000 hours of flying. He retired as a captain in July 1986, becoming the first African American to reach retirement age, then 60, with a commercial airline.