Trippe’s interest in flying led him to begin the first aviation club at Yale.

Trippe's interest in aviation manifested itself in 1917 when he began taking classes at the Curtiss Flying School in Miami. That same year, he left Yale University to become a Navy bomber pilot. Although he never saw any action, Trippe returned to Yale so captivated by flying that he founded the university's first aviation club.

After graduation, Trippe attempted a conventional Wall Street career, but soon realized his true passion lay in flying. He began making plans to start a new airline. Based in New York, his company would fly to foreign cities. Backed by rich friends, Trippe opened the offices of Pan American Airways in 1927. Taking advantage of his connections with the political elite, he got Pan Am the first U. S. government air mail routes to the Carribean. As a young man, Juan Trippe - named after his mother's favorite aunt, Juanita - started calling himself Terry, a seemingly more appropriate name for someone from a prosperous family of White Anglo Saxon Protestants. Hoping to negotiate better deals if foreign business associates assumed he was Spanish, Trippe switched back to using the name Juan.

Trippe began a life-long friendship with Charles Lindbergh in 1928 when he asked Lindbergh to serve as a consultant to Pan Am.

Throughout his career, Juan Trippe had an uncanny ability to foresee changes in the aviation industry before they happened. Trippe's early bid to dominate the overseas routes gained an enormous boost when he succeed in convincing the most famous aviator in the world, Charles Lindbergh, to work for his airline. Trippe flew with Lindbergh as they mapped out new air routes for Pan Am in the early 1930s. Sharing a belief in aviation's ability to open up new worlds, the two would remain life-long friends.

Trippe was able to use his family’s old sea merchant logs to help Pan Am plot a course across the Pacific.

In 1934, Trippe made a startling announcement, "Pan Am is going to conquer the Pacific." Flying an airliner across the Pacific was thought to be impossible, since there were not enough places to land and refuel in the vast stretch of open water between America and China. Trippe went to the office of the postmaster general with a proposition: if Pan Am found a way to cross the Pacific, it would be guaranteed all of the airmail contracts to the Far East. Surprisingly, the Roosevelt administration agreed to this monopolistic deal. They decided that it was in the national interest to allow Pan Am to do what it had done in the Caribbean - blaze a path behind which American business and the American military could follow. Trippe spent millions to oufit a ship that would sail to Wake Island, a tiny piece of land that he knew almost nothing about, and build an airport. Over the course of nine lonely months, they transformed the three square mile island from an almost barren, uninhabited wasteland into a bustling town with streets, a dock and a seaport. Pan Am Clippers were soon crossing the Pacific. Juan Trippe's gamble had paid off for Pan Am.

In the early 1950s, aircraft manufacturers were decidedly uninterested in building passenger jets, arguing that jet engines - which had been introduced into military aircraft during World War II - burned too much fuel to be economically viable and that the traveling public was perfectly content flying in propeller airplanes. Juan Trippe disagreed. He thought Pan Am could benefit enormously from the development of large commercial jetliners. Unfortunately for Trippe, the aircraft manufacturers didn't want to make the new planes. Pitting one manufacturer against the other, Trippe lured both Boeing and Douglas into the jet building business. Both companies benefited from Pan Am's orders, but it was Juan Trippe who ultimately was the big winner. He got the large new jet he wanted - the Boeing 707. Pan Am soon had an unheard of 90% occupancy on its fleet of jets.

Before retiring, Juan Trippe was ready to take one last gamble. Trippe's goal since the end of World War II had been to transform air travel from an elite experience into one that was affordable for the masses. By the early 1960s, air travel had become so popular that airports were struggling to handle the constant stream of small jets. To solve the problem, Trippe envisioned a jumbo jet, a true oceanliner of the air. Trippe sold Boeing on his idea for the new plane, the 747. The jumbo jet proved to be a huge gamble not only for Trippe, but for Boeing, which had been driven to the brink of bankruptcy developing it. Competing airlines were forced to keep pace with Pan Am and orders for the 747 soon came pouring in. The 747 was the last in a long line of airplanes that Juan Trippe insisted had to be built.

By the time Trippe retired in 1968, Pan Am was flying to 85 nations in 6 continents. Trippe died in 1981, his vision of a world where more people flew for less money had become a reality.