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Born on the Southside of Chicago, Wilson started boxing in 1980 at the age of 14. He was coached by Tom O’Shea. Wilson was an amateur standout and was the 1993 National Golden Gloves Light Middleweight Champion. He later went on to become the United States Amateur Light middleweight champion in 1997–1999. Chicago Golden Gloves finalist (1986). He won the Chicago Golden Gloves from 1990-1992 U.S. Olympic alternate (1996).