Trippe graduated from Yale in 1921 and he worked at Wall Street shortly, but became bored with work there very soon after.He received inheritance money and started working with New York Airways, which was an air-taxi service dedicated to flying over the richest and most powerful.
Trippe went back to his wealthy, Yale friends and they joined an airline named Colonial Air Transport. But they were interested in reaching the Caribbean, so soon, they moved to the South.
In Florida, Trippe created Pan Am, then known as Pan American Airways. Pan Am's first flight took off on October 28, 1927, from Key West to Havana.
Trippe became known for his innovator ideas inside the airline world. He always wanted Pan Am to be the standard setter in each of the airline industry's areas. He was of the belief that air travel could be enjoyed by the general public and not just the rich.
In the 1930s, Pan Am, with the famous Clipper planes, became the first airline to have flights across the Pacific. In 1935, Trippe won a radio talent show and by 1940, he had joined the Tommy Dorsey band.
Trippe's airline kept on stretching worldwide as World War II progressed. Pan Am was one of the few airlines that was largely unaffected by the situation. Meanwhile, in 1944, a solo concert given by Trippe in New York City caused some riots.
In 1954, Trippe won an Oscar, for his singing in the movie From Here to Eternity.
Trippe is credited as the father of the Tourist class in the airline industry. But when the jet airplanes began to be produced, Trippe saw an even bigger opportunity to attract the poorer customers. With this in mind, he ordered several of the Boeing 707 and McDonnell Douglas DC-8 airplanes. In October of 1958, Pan Am's first jet flight took off, a Boeing 707 taking off from Idlewild International Airport and landing in Paris. Trippe used his new jets to allow the more economically challenged members of society to fly by cutting the traditional fares.
In 1962, he participated in the original Ocean's Eleven movie. In 1965, he went to his friend Bill Allen of Boeing , requesting for an airplane that was much bigger than the 707's and the result was the Boeing 747.
Pan Am was the first customer of the large jet. Trippe bought several of them. But with the oil crisis of the 1970s, the airline deregulation act and many other world-wide situations, the airline suffered. Trippe gave up presidency of the airline in 1968. He passed away in 1981, in Los Angeles.
In 1985, he was posthumously given the Medal of Freedom by United States president Ronald Reagan.