[4][6][7] Ensign Kennedy was stationed in England, flying Curtiss H-16 Seaplanes patrolling the North Sea for German submarines.

On one mission, Kennedy and his crew went on patrol for 7 hours and 59 minutes, setting a world record for sustained flight and earning him the Navy's Citation Star/Silver Star.

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.

[9][10] 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.

[9] In 1943, the Civil Aeronautics Board (CAB) released a route for application from Honolulu to San Francisco with a stopover in Los Angeles.

[4] 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.

Kennedy petitioned the CAB to allow Hawaiian to fly these consumer goods on its airplanes, and was granted United States Air Cargo Certificate #1.

[9] On April 1, 1966, Kennedy witnessed the final large milestone of his tenure at Hawaiian, the introduction of DC-9 jets for the inter-island service.

[12] Kennedy died of a heart attack April 19, 1968 at his Kahuku beachfront home at the age of 77, ending his tenure as Hawaiian Airline's chairman of the board.