11/19/2025
Even though Puerto Rico was a US territory, the air mail routes to the island were considered foreign air mail routes prior to the Second World War. Dennis Powelson, a company pilot for the Don Q rum distillery, established his own airline in 1938, Powelson Line, to get the air mail contract.
The following year he rebranded as Caribbean Atlantic Airways (CAA) Using Stinson Tri-Motors, the airline flew its first services in 1942 between San Juan and the Virgin Islands. Postwar, the airline was branded as Caribair and was purchased by Dionisio, Benigno and Juan Trigo, three brothers with their own import-export business.
Caribair's services proved popular and the workhorse DC-3s that replaced the Stinsons were joined by Convair 340/440s as international services to the other islands of the Caribbean were added (the first being the Dominican Republic in 1948). In 1965, some of the Convairs were converted 640s with the re-engining with Dart turboprops.
Also in 1965, Caribair ordered its first Douglas DC-9s and inaugurated services the following year. They were the first Puerto Rican airline to operate pure jets. By 1968, Caribair had phased out the DC-3s and the fleet consisted of the DC-9 Series 30 and the Convair 640s.
Ambitious expansion put a crunch on Caribair's finances and by 1970, the airline needed cash badly.
Wanting to expand its Caribbean network, Eastern offered to buy Caribair and moved to manage the airline starting in 1970 pending merger approval by the Civil Aeronautics Board. Oddly, the CAB voted against the merger in deference to Pan Am who opposed Eastern's expansion.
Things got weird in 1972 when President Nixon urged the merger take place to save Caribair jobs to help Puerto Rico's governor, Luis Ferre, who was facing a tough re-election fight against challenger Rafael Colón who ultimately won.
In 1973, the merger was approved and Caribair was absorbed into Eastern Air Lines.
Images: Ed Coates, Carlos M. Rivera-Cuesta, William Sierra, Francisco Rodriguez