Taylor, who began boxing officially at age 13, earned numerous accolades throughout his amateur career, starting with his achievement of the 1996 Under-19 Championship. He went on to win a pair of Police Athletic League Championships and National Golden Gloves titles and he finished second and third at the 1997 and 1998 United States Championships, respectively. In 1998, Taylor won a bronze medal at the Goodwill Games. Then, in 2000, he earned a spot on the Olympic Boxing Team, becoming the first boxer from Arkansas ever to compete in the Olympic Games. Competing at the 2000 Olympics in Sydney, Australia, Taylor ended up winning the bronze medal.
During his reign as champion, Taylor won a rematch against Hopkins and defeated Kassim Ouma and Cory Spinks, as well as fighting Winky Wright to a draw.
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