Bailey emigrated from Jamaica to Canada at age 13, and played basketball before his graduation. Although participating in athletics as a hobby, he didn't take up the sport seriously until 1994. By that time, he was an extremely successful stockbroker.
The following year saw his international breakthrough. At the World Championships in Gothenburg, Bailey surprisingly won the 100 m and also won the 4 x 100 m title with his teammates.
He repeated that double at the 1996 Atlanta Olympics, setting a world record of 9,84 in the 100 m (the previous record was set in July 1994 by Leroy Burrell at 9,90). He won a third world title in 1997 with the Canadian relay team, while finishing second in the individual event behind Maurice Greene.