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.