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Pan American World Airways could be considered a corporate Cinderella—a rags-to-riches-and-back-again phenomenon.

From its founding in 1927 and its relatively obscure inauguration as a mail carrier on a 90-mile mail run from Florida's Key West to Cuba, Pan Am's route system grew to span the globe. The company that would eventually become famous for its blue-and-white-world logo grew into a conglomerate of hotels, airlines, business jets, real estate, a helicopter service, and even a guided m...