Harold Gray was an American pilot and executive for Pan American World Airways who served as CEO from 1968 to 1969.

Harold attended the University of Iowa, but dropped out after his sophomore year to take flight training at the Army Air Corps Training Center in San Antonio, Texas. He later graduated from the University of Detroit with a degree in aeronautical engineering.

In 1928, Gray was working for Sky View in Miami when met the staff of Pan Am. He was hired as the company's the tenth pilot. His first assignment was to fly a hazardous route over the jungles of South America.In 1934 he qualified as Pan Am's first master of ocean flying boats. Between 1937 and 1939 he piloted Pan Am's first survey flights to Bermuda, Ireland, Southampton, the Azores, Lisbon, and Marseille.

On March 29–30, 1939, Gray piloted the Yankee Clipper on the first ever trans-Atlantic passenger flight. The first leg of the flight, Baltimore to Horta, Azores, took 17 hours and 32 minutes and covered 2,400 miles. The second leg from Horta to Pan Am's newly-built airport in Lisbon took 7 hours and 7 minutes and covered 1,200 miles. Following the flight, Gray described the flight over the radio for the National Broadcasting Company.

In 1941, Gray piloted the Cape Town Clipper on what was then the world's longest proving flight. He flew 19,000 miles from La Guardia Airport in New York City to Léopoldville in the Belgian Congo and back.

In July 1964, Gray was elected president of Pan Am and in May 1968 was elected as chairman and chief executive officer.