On August 6, 2008, Tillman was sent home from a team board meeting because he was acting strangely. After he arrived home, Tillman put his hands on the hips of his children's sixteen-year-old babysitter. Tillman's attorney would state that Tillman was not thinking clearly because he had taken a double dose of sleep aids and pain medication for a sore back and that he did not remember what happened. On January 27, 2009, Tillman was charged with summary sexual assault. He was placed on paid administrative leave by the Roughriders on February 2, 2009.