Juan Trippe’s close call

“Best Laid Plans” Department: Did you know that but for the sheerest stroke of luck, Juan Trippe’s dream of building an international airline might have ended before it ever began? In 1927, Pan American Airways founder Trippe had managed to secure a U.S. Air Mail contract for the route between Key West and Havana — on one condition: The first Air Mail delivery had to take place on or before October 19, 1927 — no extensions allowed. The airline was still so new that its incorporation with Trippe at the helm was only consummated on October 11th — eight days before the deadline. Trippe’s crew in Key West worked frantically to clear runways and finalize the installation of a hangar and ticket office but then disaster struck: Four days before the October 19 deadline it began to rain–and it kept on raining. The “airport” became a swamp. The Fokker VII land plane that Pan Am had lined up for the flight arrived in Miami from New York but couldn’t continue to Key West because it couldn’t land on the inundated airfield. Even worse, Pan Am had agreed to forfeit a $25,000 performance bond if it failed to meet the terms of the Air Mail contract. Pan Am’s Capt. John Whitbeck, who was supervising the airport installation in Key West, put in desperate calls to airports around the country looking for a seaplane that Pan Am could charter. Then came a stroke of luck: Whitbeck got wind that a Fairchild FC-2 seaplane, “La Nina,” belonging to Basil Rowe’s West Indian Aerial Express, had put up at Miami’s N.E. 8th Street Marina for repairs. Whitbeck contacted the Fairchild’s pilot, Cy Caldwell, and then Caldwell’s boss, Basil Rowe. Rowe was not keen on delaying his plane’s flight as it was booked by a client, but he was eventually persuaded to agree to Caldwell’s flying Pan Am’s mail to Havana for a price that is reported to have been anywhere between $175 to $250. Caldwell flew La Nina to Key West on the afternoon of October 18th for an overnight stay and was reputedly given the “royal treatment” by Pan Am while there — though Prohibition was in effect in other parts of the country, liquor still flowed freely in the Keys. The next morning, at 8:04 AM on October 19th, Caldwell took off with the mail. He arrived in Havana an hour and two minutes later, thus saving the day for Pan Am and earning himself a permanent place in U.S. aviation history. Some nine days later, on October 28, 1927, landing conditions at Key West had improved and Pan Am was able to inaugurate its first regularly scheduled mail flight service between Key West and Havana, on the Fokker VII tri-motor “General Machado.” Rowe later sold his West Indian Aerial Express to Pan Am, joining the company and becoming one of the airline’s most highly awarded and famous pilots.