Hill appears to have had some experience of flying before he enrolled in autumn 1912 in the Glenn Curtiss Flying School, in order to study flying thoroughly. He was issued land plane certificate No. 234 by the Aero Club of America. Between 1915 and 1924, Hill pursued a career as an aircraft instructor, test pilot and aircraft sales representative in several different locations in the central and eastern United States.[1]
Bertaud's elimination from the crew of Columbia spurred him to make his own attempt at a transatlantic flight, this time from New York to Rome, Italy, and Hill agreed to join him. William Randolph Hearst agreed to sponsor the attempt to publicize his newspaper, the New York Daily Mirror. The newspaper's editor, Philip A. Payne, accompanied the two pilots on the flight.
The three took off, with Hill at the controls, in Old Glory, a Fokker F.VIIA monoplane, from Old Orchard Beach, Maine, at 12.23 pm EST on 6 September 1927. The Old Glory had last been sighted by the steamship California at 11.57 pm, 563 km east of Cape Race. At 3.57 am and 4.03 am distress signals from the aircraft were received by radio; its estimated position was then 960 km east of Cape Race, Newfoundland. On 12 September, the SS Kylefound substantial amounts of wreckage from the aircraft, but no trace was ever found of Bertaud, Hill or Payne.[1]