#5 Miguel Cotto:
The final entry in this list bears the name of Puerto Rican Miguel Cotto, who represented his nation at the 2000 Sydney Olympics. Cotto was just 19 years old back then, and was handed the toughest draw possible in the light welterweight division.
The reigning World Champion from Uzbekistan, Mohamad Abdullaev proved too strong for the young Puerto Rican and Cotto was beaten comprehensively by 17-7.
Abdullaev went on to win the gold medal, but Cotto forged a fantastic career in professional boxing. He quite fittingly got his revenge against Abdullaev in the professional circuit. Five years after the Sydney Olympics, the 2 squared off in Madison Square Garden, where Cotto won in 9 rounds, with Abdullaev having to surrender thanks to a closed right eye.
Cotto is one of few boxers who have won the world title in 4 different weight categories. Cotto became a quadruple champion by winning the welterweight, light middleweight, lineal middleweight and light welterweight categories.