walcott first challenged for the lightweight championship on october 29, 1897, at the lennox athletic club in new york, but was tko'ed by the champion george "kid" lavigne in the 12th round. he was also unsuccessful in his first attempt to win the world welterweight championship when mysterious billy smith outpointed him on december 6, 1898. likely his most frequent opponent, walcott fought smith six times in his career.