On August 23, 2007, Boston was arrested in Pinellas Park, Florida and charged with DUI after a failed sobriety test was conducted. Boston was released on his own recognizance. Boston's breath test resulted in a reading of 0.00 BAC. On September 10, 2007 it was released to the media that David Boston tested positive for GHB, a recreational drug with questionable ties to bodybuilding. After learning of the drug charges the Buccaneers quickly came to an injury settlement with Boston allowing him to be released. On September 12, 2007, Boston was officially released by Tampa Bay when they decided to sign Mark Jones. On December 1, 2011, Boston was accused of beating a woman after a night of drinking in Boca Raton. Boston allegedly punched the woman twice in the head, leaving a gash requiring 10 Stitches, according to a Boca Raton police report. Boston pleaded guilty to a charge of aggravated battery and received a six-month prison sentence. Judge Charles Burton said that he was extending leniency to Boston, turning down the prosecution's request for a term of four years, because of medical evidence that the defendant had incurred permanent brain injuries from the four concussions he sustained during his playing days.