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.
The following year was 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 Olympics in Atlanta, 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 relay team, while finishing second in the individual event behind Maurice Greene.
After that season, Bailey struggled with injuries and never reached his previous level of performance. He retired from the sport in 2001.
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