Holmes has acknowledged selling drugs on the street corner of his hometown of Belle Glade, Florida as a teenager; he says that his mother's influence and a desire to play professional football made him decide to stop.
Holmes was arrested in Miami Beach, Florida on May 27, 2006 for disorderly conduct. Charges were subsequently dropped after Holmes paid a fine. Holmes was arrested for a second time on June 18, 2006 for domestic violence and assault in Columbus, Ohio.
On July 7, 2006, Holmes appeared in Franklin County Court in Columbus, Ohio for both a pre-trial regarding the domestic case and hearing regarding the traffic ticket. He plead no contest to the traffic ticket and agreed to pay a fine. While Lashae Boone, the mother of Holmes' daughter and the victim in the assault case, requested that the domestic violence and assault charges be dropped, the prosecutor refused. Boone and their daughter accompanied Holmes to court. The charges were later dropped.
On October 23, 2008, Holmes was arrested in Pittsburgh and cited by officers for possession of marijuana. Holmes released an apology after missing a game, stating that he wished to "focus all of [his] efforts on helping our team win on the field and achieve its ultimate goal."