The Mysterious Captain J.K. Montgomery

LXXXIV

The tale of Pan American Airways’ beginnings is a tangled skein of plot and counterplot, murky because much of it is lost in the mists of time, murkier because accurate records were not kept, and murkier still because the men involved wanted it that way. It is a story of backroom deals and backstabbings that are as dismayingly exciting as they are fascinating. One of the difficulties in untangling the knotted skein is that everything happened so fast --- within a few weeks from June to October 1927 --- that it is difficult to determine who was doing what when and where and to whom.  

Sometime while he worked to acquire landing rights in Cuba, Juan Trippe managed to create a parent company for Pan American, the Aviation Corporation of America (ACA). ACA promptly began swallowing small, undercapitalized airlines. 

Airlines came and went in those days; many had one airplane, others --- like Pan Am on October 19, 1927 --- none. Some were paper tigers. Besides battling Rickenbacker and Stout for landing rights in Cuba, Juan was also battling other men for the airmail contract itself. 

Captain J.K. Montgomery (variously identified as a retired Army Air Corps flier or Naval Air Service flier), who according to one version of the Pan Am legend, created the airline himself and then asked Trippe to fund it, and according to another version of the story already owned Florida Airways, ultimately founded American International Airways with the backing of investment banker Richard B. Bevier. It was a seaplane line focusing on inter-island travel, created primarily to grab the airmail route to Havana (but wasn’t that why Montgomery had allegedly founded Pan Am? And if he already had an airline with landing rights and routes, why start two more? What happened to J.K. Montgomery, who just suddenly vanished from all versions of the story? According to the book Anti-History by Gabrielle Durepos, Montgomery is a George Kaplan-esque figure).

While Montgomery and Bevier created AIA, Richard Hoyt, another investment banker, created Atlantic, Gulf & Caribbean Airways to grab the airmail route to Havana and provide air service to the Canal Zone. Somewhere between the two of them, AIA and AG & C may have owned an aircraft or two. Compared to Eastern Air Lines (Rickenbacker’s company) and Stout Air Service (Stout’s company), these two were also-rans, but in the chaos that was early aviation, the U.S. had granted them routes. Juan Trippe stepped in, bought them up, divvied up some stock, and gave everybody a title with a commensurate salary. Suddenly, Pan American had routes extending from Atlanta south through Florida and the Caribbean basin.  It had only to develop them. 

For a man who was only 28, Juan Trippe had a remarkable ability to stay on task. He was like the proverbial hummingbird who, visiting the mountain once every thousand years to sharpen its beak, wears the mountain down to a flat plain. He always came to the table knowing exactly what he wanted and he argued with men --- many older and far more experienced at business than he --- until he got it. He had, it was said, “an intuitive, dreamlike sense of where aviation could go,” often based on wishful thinking, but bonded to the same kind of intuition when negotiating. He seemed to know just when men would crack, what they wanted, and what they would settle for. And he never backed off.