Navy pilot Charles Elliott as Chief Pilot and Army pilot Carl Cover as Operations Manager. Kennedy, Cover, and Elliott, all being WWI veterans, decided on Armistice Day (November 11) to be the inaugural flight in the Sikorsky S-38 amphibious airplanes. On November 11, 1929, Kennedy's dream of scheduled airline service in the Hawaiian Islands took flight as Elliott and Cover flew the two Sikorsky's in formation from Honolulu to Maui, then on to Hilo. Starting an airline the month after the Wall Street Crash of 1929, was a daunting task. However, the Board of Directors had great faith in Kennedy, making him the President of both Inter-Island Steam Navigation and Inter-Island Airways in February 1933. The airline lost money for the first 5 years, until Kennedy was able to secure the airmail contract starting on October 8, 1934. This allowed Kennedy to start looking for larger airplanes to operate, and 10 days after the maiden airmail flight he decided on the Sikorsky S-43, making Inter-Island Airways the launch customer for this new aircraft. Expanding beyond the islands Kennedy now aimed at expanding Inter-Island Airways to fly to the US mainland. To represent this, on October 1, 1941, Kennedy changed the airline's name to Hawaiian Airlines. In 1943, the Civil Aeronautics Board (CAB) released a route for application from Honolulu to San Francisco with a stopover in Los Angeles. Kennedy and TWA's president, Jack Frye, teamed up on the petition where Hawaiian would fly the routes, TWA would withdraw its application in exchange for 20% ownership of Hawaiian Airlines. Kennedy spent a great deal of time and money traveling to Washington, D.C. arguing Hawaiian's case to the CAB, but since Pacific Overseas Airline submitted they didn't get a chance at the application, the CAB decided to start the entire application process over again, but it was too expensive for Kennedy to attempt once more. The route application process resurfaced in 1959, after Kennedy had handed over the Presidency to Art Lewis, but remained on as chairman of the board. This time Hawaiian was flying DC-6s to the mainland on charters, and felt they had an excellent chance to win the route. Once again to no avail, the route was awarded to Western Airlines. Kennedy would never get to see his airline fly to the mainland on a scheduled basis, as Hawaiian would have to wait until the Airline Deregulation Act of