Taylor turned professional in 1896, at the age of eighteen, and soon emerged as the "most formidable racer in America." Taylor's first professional race took place in front of 5,000 spectators on December 5, 1896. He competed in a half-mile handicap event on an indoor track at New York City's Madison Square Garden II on the opening day of a multi-day event. Although the main event was a six-day race from December 6–12, other contests in shorter distances were held on December 5 to entertain the crowd. These races included the half-mile handicap for professionals in which Taylor competed, a half-mile race between Jay Eaton and Teddy Goodman, and a half-mile scratch race. In addition, there were half-mile scratch and handicap races for amateurs.