Taylor, who began boxing 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 (PAL) 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.
He made his professional boxing debut in 2001 and won his first 23 bouts, which included victories over former champions Raúl Márquez and William Joppy. On July 16, 2005, Taylor defeated Bernard Hopkins to win the undisputed middleweight championship, claiming The Ring magazine middleweight championship and the middleweight titles from the four major boxing organizations.
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. On September 29, 2007, Taylor suffered his first professional loss to Kelly Pavlik and lost a rematch to Pavlik on February 16, 2008. Afterwards, Taylor moved up to the super middleweight division. In his first fight in the weight class, Taylor defeated Jeff Lacy to earn a fight against World Boxing Council (WBC) super middleweight champion Carl Froch. Taylor, ahead on two of the scorecards, lost the bout to Froch by technical knockout in the final round.
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