Trippe was born in Sea Bright, New Jersey, on June 27, 1899, the great-great-grandson of Lieutenant John Trippe, captain of the USS Vixen. Because of his Spanish first name, people often assume that Trippe was of Cuban descent, but his family was actually Northern European in ancestry and settled in Maryland in 1664. He was, in fact, named after Juanita Terry, the Venezuelan wife of his great uncle. Trippe graduated from The Hill School in 1917. Attending Yale University as America entered World War I, he left Yale and, along with some of his Yale classmates, applied for flight training with the U.S. Navy. After completing training in June 1918, he was designated as a Naval Aviator and was commissioned as an Ensign in the U.S. Naval Reserve. However, the end of World War I precluded him fr