Bolden was arrested October 11, 2003 in Atlanta, Georgia on charges of possession of a stolen vehicle and violation of Georgia's controlled substances act. He was not indicted on the drug charge, and on April 14, 2004 pleaded no contest to possession of a stolen vehicle. The vehicle aforementioned which was purchased from a friend that unbeknownst to him was stolen. He was sentenced as a first-time offender to three years probation and ordered to pay a $3,000 fine.
On April 30, 2007, he was released by the Bucs and returned to the Winnipeg Blue Bombers of the CFL. After missing the last three games of the season as well as the post-season games, Bolden was released before the 2008 training camp on May 27, 2008.