In 1926, Pyle signed Lenglen and several of the best tennis players in the world to start the first professional tennis tour, which traveled throughout the U.S. and Canada. Two years later, he inaugurated the first Trans-American Footrace, known as the Bunion Derby, an ambitious, 3455-mile-long foot race from Los Angeles, California, to Chicago, Illinois, to New York. While the 1928 race was not a financial success, Pyle organized a 1929 "return" along essentially the same route, but from New York to Los Angeles.
After managing the "Ripley's Believe It or Not" exhibit in the Chicago World's Fair, Pyle married comedienne Elvia Allman Tourtellotte in 1937. He became president of the Radio Transcription Company, a position that he held until his death of a heart attack in Los Angeles, February 3, 1939.