In 1989, Stuart was serving as the general manager for Edward F. Kakas & Sons, furriers on Newbury Street. Stuart's wife, Carol (née DiMaiti, born March 26, 1959, in Boston), was a tax attorney, and pregnant with the couple's first child. On October 23, the couple were driving through the Roxbury neighborhood after attending childbirth classes at Brigham and Women's Hospital. According to Stuart's subsequent statement, a black gunman with a raspy voice forced his way into their car at a stoplight, ordered them to drive to nearby Mission Hill, robbed them, then shot Charles in the stomach and Carol in the head. Stuart then drove away and called 911 on his car phone.