Early airlines, especially in the 1920s and 1930s, struggled to turn a profit without a lucrative airmail route contract. In July of 1927, Pan American Airways was awarded the overseas airmail route from Key West, Florida to Havana, Cuba, with a deadline to start service by October 19, 1927. Although the company acquired a Fokker F.VIIA-3m to fly the 90-mile route, various issues including rainy weather conditions delayed the construction of a suitable runway for the aircraft in Key West. Scrambling to find an aircraft and a pilot to fulfill their contract, Pan American hired West Indian Aerial Express's pilot Cy Caldwell and modified their Fairchild FC-2 landplane with floats to be able to take off from Key West and land in Havana. Carrying seven bags of mail, Cy Caldwell inaugurated Pan American's first ever service #onthisday in 1927. Nine days later, Pan American's Fokker F.VIIA-3m took over the route, inaugurating scheduled service. This image was posted on October 19, 2022.