Simon turned pro in 1994 and won the WBO Light Middleweight title in 1998 by defeating Winky Wright by controversial decision. The bout had initially been ruled a draw, but then a “scoring error” was discovered, favoring Simon. He defended the title four times against Kevin Lueshing, Enrique Areco, Rodney Jones and Wayne Alexander. He later captured the WBO Middleweight title against Sweden’s Armand Krajnc in a 12 round unanimous decision. In 2002 Simon was involved in a serious car accident sustaining him injuries that prevented him to defend his title, due to this he was stripped of the belt.
Simon returned to boxing in March 2007, winning an eight round decision over Stephen Nzuemb, in Namibia. He won a fight against Tanzanian Rashid Mutumla by knockout on 2 December 2010.
Following his release from jail in 2009 Simon launched a comeback, recording several wins over journeyman opposition. In his most recent outing in June 2012, Simon stopped journeyman Ruben Groenewald at 1:23 of the first round after knocking him down twice. Simon weighed over 200 pounds, the heaviest of his career.
