Harold was born on May 17, 1906 in rural Geneseo, Illinois..
With a flying career of 70 years, Harold logged nearly 30,000 flight hours, which is the equivalent of ten years and one month of continuous flying.
He was the first pilot to fly non-stop from Paris to Chicago, after which he presented Mayor Richard Daley with a statue of the Eiffel Tower. This flight made O'Hare Airport an International Airport.
As a captain for TWA for 30 years, Harold set multiple speed records for international routes.
He won permanent possession of the Greve Trophy because he won three consecutive races.
Harold won the Thompson Trophy in 1935 at the National Air Race in Cleveland OH. He was also awarded America's #1 Pilot by National Aeronautical Association in 1935.
He is acknowledged in the Smithsonian National Air and Space Museum “Golden Age of Flight” exhibit, for winning the 1935 Thompson Race in Cleveland Ohio.
Besides his racing career and piloting TWA flights, Harold was also a barnstormer and a skywriter.
Harold was the first TWA pilot to fly passengers over the North Pole.
His first pilot's license was signed by Orville Wright in 1929.