In 1989, Charles ‘Chuck’ 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, despite his injuries, and called 911 on his car phone. On the night of the crime, the CBS reality television series Rescue 911 was riding with Boston Emergency Medical Services personnel. The crew took dramatic footage of the couple being extricated from the car: Carol can be seen “in profile, her pregnancy prominent, being wheeled to the ambulance.” Other footage included Charles Stuart straining to speak with ambulance workers, and graphic scenes of his rushed entry to the hospital’s emergency room.

Carol Stuart died just hours after the shooting, at approximately 3:00 a.m. on October 24. Her funeral took place four days later at St. James Church in her native Medford. Shortly before her death, doctors delivered her baby by caesarean section, two months premature. Baptized in the intensive care unit, the child was given the name Christopher, according to Charles and Carol’s prior wishes. Christopher had suffered trauma and oxygen deprivation during the shooting, and died seventeen days later. A private funeral service was held for Christopher on November 20, 1989. Boston Police searched for suspects based on Charles Stuart’s description of the assailant. Though investigating officers asked doctors whether Stuart’s wounds could have been self-inflicted, they were told that this was very unlikely, given the severity of the injuries. Police found a young man, Willie Bennett, who fit Stuart’s description. On December 28, Stuart identified Bennett as his attacker in a lineup. The case against Bennett abruptly collapsed on January 3, 1990, when Charles Stuart’s brother Matthew identified Charles as Carol’s killer. Matthew admitted that he had driven to meet Stuart that night to help him commit what he had been told was to be an insurance fraud. Upon arrival, Matthew said that he had seen that Carol had been shot, and that his brother had shot himself to make it appear as a carjacking. Matthew took the gun and a bag of valuables, including the couple’s wedding rings, and threw them off the Pines River Bridge in Revere. Some of the items, including the gun, were later recovered. As Stuart had blamed the incident on an African-American male, and the information provided by his brother led the police to conclude this was not true, racial tensions were heightened in Boston for a time.

Police later learned that Stuart had been upset at the prospect of becoming a father, particularly worried that his wife would not go back to work and their financial status would be diminished. Stuart had also started some sort of relationship with Deborah Allen, an employee at Kakas & Sons, though Allen denied any romantic involvement. The Boston Globe reported that a $480,000 check was issued to Charles Stuart in payment for a life insurance policy on his wife, but no such check was ever found. The television show Cold Blood reported and confirmed that Charles Stuart received a $100,000 life insurance check, which he cashed just after being discharged from the hospital. Stuart also bought a new Nissan Maxima for $16,000 in cash. On January 4, 1990, hours after his brother Matthew revealed the truth to police, Charles met with his lawyer. Shortly afterward, Stuart’s car was found abandoned on the Tobin Bridge in Chelsea. A note was found in Stuart’s car, stating that he was “beaten” by the “new accusations” and was “sapped of [his] strength.”  Stuart’s body was found in the Mystic River the next day. Investigators later discovered that Stuart had previously expressed a desire to kill his wife. In 1991, Matthew Stuart was indicted for obstruction of justice and insurance fraud for his role in covering up the crime. An associate of Matthew, John McMahon, was also indicted as an accessory to murder. Stuart pleaded guilty in 1992 and was sentenced to three to five years in prison. He was released on parole in 1997, but was later rearrested for cocaine trafficking. On September 3, 2011, Matthew Stuart was found dead from an apparent drug overdose in Heading Home, a homeless shelter in Cambridge.