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While still on probation, Camacho, then 17, and a friend were involved in a carjacking during which his friend stabbed the car's driver. Camacho went to prison at Rikers Island for three and a half months. As on the streets, Camacho was involved in numerous fights in prison and landed in solitary confinement. It was an eye-opening experience for Camacho, who realized that he was jeopardizing his dreams of becoming a world-class boxer. He was also concerned about his young son, Hector, Jr., born to a former girlfriend when Camacho was 17.
By the time Camacho landed at Rikers Island, he had already won the New York Golden Glove championship. He would go on to win for three consecutive years. Camacho had begun boxing when he was ten years old. Restless and full of energy, Camacho found that boxing at the local boys' club gave him a much needed outlet for his aggression. His determination and exceptional quickness, along with his legendary cocky attitude, began to earn Camacho some amateur fights.
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