Stuart shooting timeline
It began at 8:43 p.m. on the night of Oct. 23, 1989 — but really, it goes back much further than that. Explore a timeline of the events leading up to the shooting on Mission Hill that rocked a community, shattered lives, and exposed racial fault lines.
Oct. 13,1985
Chuck Stuart and Carol DiMaiti wed
Chuck Stuart and Carol DiMaiti are married at St. James Church in Carol’s hometown of Medford. They couple began dating in 1981 after meeting at the Driftwood restaurant on Revere Beach, where he was a cook and she was a server.
Early1989
Chuck and Carol prepare for a growing family
Carol learns she’s pregnant in early 1989. The couple live in Reading, a suburb north of Boston, and start preparing for their growing family. She’s a tax lawyer at a publishing company, while Chuck is general manager at a fur store in downtown Boston.
Aug./Sept.1989
Chuck approaches people about killing Carol
Chuck tells two people — his brother Michael and his high school friend David Frank MacLean — that he wants his wife dead, according to police interviews and grand jury statements. Chuck is not excited to be a father and he believes Carol has the “upper hand” in the relationship. Both men refuse to assist Chuck in killing Carol. Neither alerts the authorities.
October1989
Chuck pitches his brother on an insurance scam
Chuck goes to his youngest brother Matthew and suggests they pull an insurance scam, by staging a robbery of his home in Reading. They attempt to pull off the robbery in mid-October at Chuck’s home but are interrupted by Carol and and call it off.
Oct. 22,1989
The brothers plan another staged robbery
After discussing a new insurance scheme, Chuck drives Matthew to Mission Hill and walks him through a proposed jewelry heist. He tells his brother to wait for him on a deserted street in the neighborhood the next night.
Oct. 23,1989
The Stuarts leave a birthing class at Brigham and Women’s Hospital
The birthing class is the last time anyone sees Carol Stuart before the shooting. Kim Woodward, an attendee of the class, later tells the Globe that Carol had a ton of questions that night and Chuck appeared nervous. “He just really was out of it.”
Oct. 23,1989
Matthew meets Chuck in Mission Hill
Matthew goes to a meeting spot in Mission Hill and meets his brother — as planned. Chuck tosses him a bag and Matthew drives off, Matthew says later.
8:43 p.m.,Oct. 23,1989
00:00
00:00
Chuck Stuart calls 911
Chuck calls 911 from a car phone in his Toyota Cressida. He tells an emergency dispatcher that he and his wife were shot by a carjacker somewhere near the hospital. He says his wife was shot in the head.
About 9 p.m.,Oct. 23,1989
Police locate the Stuarts’ car
Using the sound of sirens to locate the Stuarts, emergency responders find their car on St. Alphonsus Street in the Mission Hill neighborhood. Carol is in critical condition, with a gunshot wound to the head. Chuck is bleeding out, after being shot in the gut. Carol is transported to Brigham and Women’s, where she gives birth to a baby boy via C-section. Chuck tells police that the shooter was a Black man in a track suit.
about 10 p.m.,Oct. 23,1989
Matthew returns home, discovers the gun
Matthew says later he returns to the family home and learns from other family members that Chuck and Carol have been shot. When he realizes there is a gun in Chuck’s bag, he goes to his friend Jack McMahon. Matthew and Jack dispose of the gun and the bag in the nearby Pines River. They keep Carol’s diamond engagement ring.
around 10:30 p.m.,Oct. 23,1989
Mayor Ray Flynn pledges an aggressive response
At a Roxbury police station, Boston Mayor Ray Flynn addresses the media and calls for “every available detective” to be assigned to the case. The statement will appear that night on the 11 o’clock news.
2:50 a.m.,Oct. 24,1989
Carol dies
Medical staff pronounce Carol DiMaiti Stuart dead. She was 30 years old.
6:30 a.m.,Oct. 24,1989
Matthew and Jack begin telling people Chuck killed Carol
Matthew Stuart tells his on-again-off-again girlfriend Janet Monteforte that Chuck killed Carol. Jack tells his father, Martin, and his father’s girlfriend. Jack McMahon also tells his girlfriend, his brother Stephen, Stephen’s girlfriend, and his mother, Joyce, around this time. In the days ahead, Matthew also tells his uncle Ronald Corbett and his brother Michael.
Oct. 24,1989
Joey “Toot” Bennett allegedly brags to his friends his uncle is the shooter
While hanging out with friends, 15-year-old Joey “Toot” Bennett allegedly brags that his uncle Willie Bennett was responsible for the Stuart shooting, though he will later deny telling anyone this. Willie, known as “Wild Bill,” is a well-known criminal in the neighborhood who has already drawn the attention of the police — and Joey’s admiration. Among the friends is Dereck Jackson, 17, who tells Erick Whitney. Whitney then tells a version of the story to his mother, who tells Trent Holland, an officer in the Boston Police Department.
Oct. 26,1989
Chuck speaks to detectives for the first time at the hospital
Police interview Chuck Stuart for the first time after his operation. He gives a more detailed description of the crime and his assailant, saying the shooter told him not to look in the rearview mirror and that the man thought Chuck was a police officer. The same day, a life insurance check for Carol totaling $82,000 is made out to Chuck, who requests the check be delivered to his bedside in the hospital.
Oct. 28,1989
Carol’s funeral
Carol’s funeral service is held at St. James Church in Medford. The pallbearers include two of Chuck’s brothers, Michael and Matthew. Still hospitalized, Chuck has a letter read at the service, saying “goodbye, sweet wife.” About 800 people, including Governor Michael Dukakis and Flynn, attend.
Oct. 28,1989
Michael Dennis MacLean and a friend share the tip with the authorities
Michael “Dennis” MacLean, David Frank MacLean’s brother, is told about Chuck’s involvement and in turn tells his friend John Carlson about Chuck killing Carol. The two men later call State Trooper Dan Grabowski — who was a dispatcher the night of the shooting — to tell him the tip. They never hear back from Grabowski.
Oct. 28,1989
Boston police arrest first suspect who is publicly linked to the Stuart case
Acting on a tip, police locate a man named Alan Swanson. They arrest him and his girlfriend for breaking and entering. In the bathroom, police find a black track suit in his sink. The following day, Swanson appears in court on an upgraded burglary charge, where a dozen reporters are in attendance and bail is set at $5,000.
Nov. 3,1989
Police interview teens, ask about the Bennetts
After the story from Joey Bennett’s room reaches the police, they try to get Erick Whitney to talk. Erick’s girlfriend, Angela Brittle, is urged to bring in her boyfriend so he can share what he allegedly knows about the Stuart murder. Angela and her uncle Wilbur, a BPD cop, persuade Erick to come in in the afternoon. Erick relays his story, and is asked to contact Dereck. That evening, Erick Whitney and Dereck Jackson come to homicide with their girlfriends and are interrogated by police.
Nov. 4,1989
Erick and Dereck try to recant, are rebuffed
Erick Whitney and Dereck Jackson return to the Police Department hoping to recant. They are threatened with arrest or jail if they reverse their testimony. The boys stick to their original story, and repeat it in front of a grand jury several days later.
Nov. 6,1989
Alan Swanson is released
The Suffolk district attorney’s office, unable to make a case against Swanson for murder, reduces the charge to trespassing, a misdemeanor, and Swanson is released. Swanson is later found not guilty, and another charge of armed robbery is also thrown out.
4:34 p.m.,Nov. 9,1989
Baby Christopher dies
Christopher, Carol’s and Chuck’s baby, dies. The cause is listed as respiratory failure. He lived for 17 days.
Nov. 11,1989
The Bennetts’ homes are searched, Willie is arrested
The Boston Police Department executes three search warrants: one for Willie’s sister’s home, one at Willie’s girlfriend’s home in Burlington, and one for the Bennett family home in Mission Hill. At the Bennett family address, a SWAT team breaks down the front door with guns drawn. Willie is arrested in Burlington on a motor vehicle violation. Two days later, as police continue to build a case against Willie for the Stuart murder, he’s charged with the robbery of a video store several weeks before.
Nov. 20,1989
Christopher’s funeral is held
Relatives hold a private funeral service for Christopher, Carol’s and Chuck’s baby. Chuck is reportedly too ill to attend.
Nov. 21,1989
Willie is indicted for the video store robbery
A Norfolk County grand jury indicts Willie Bennett for one count of armed robbery and three counts of assault with dangerous weapon for the Brookline video store robbery a month before. He pleads not guilty a day after the indictment.
Nov. 22,1989
Erick and Dereck recant their testimony
Erick Whitney and Dereck Jackson retract their testimony in front of a grand jury convened to examine the Stuart case.
Dec. 5,1989
Chuck is released from the hospital
Chuck Stuart is released from the hospital. Shortly later, he issues two checks for $500 each to his brother Matthew. Matthew uses the money to buy jewelry for his girlfriend.
about 1:45 p.m.,Dec. 28,1989
Chuck identifies Willie in a police lineup
Chuck Stuart officially identifies Willie Bennett out of a police lineup. He tells the police he recognizes Willie’s jawline, even the shape of his ear, as that of the shooter in his backseat. He adds he is “99 percent sure that this was the individual that was in my car that evening.”
around 10:30 p.m.,Jan. 2,1990
Matthew decides to go to the police
Several of the Stuart siblings meet in Revere to discuss Matthew’s role. Matthew Stuart resolves to go to the police and after the meeting asks his siblings to not tell Chuck.
evening,Jan. 2,1990
The Stuart parents are told the truth
At a family meeting, without Chuck present, Matthew explains to more family members that Chuck was involved in shooting Carol.
around 7 p.m.,Jan. 3,1990
Chuck and his lawyer have a final conversation
Chuck Stuart talks to his lawyer, Jack Dawley. Their full conversation is unknown, but Dawley no longer represents Chuck when he leaves. Dawley calls Suffolk Assistant District Attorney Francis O’Meara to say he’s no longer Chuck’s lawyer, and asks if they’ve issued an arrest warrant. Chuck checks into a hotel room in Braintree.
8:45 p.m.,Jan. 3,1990
Matthew talks to the authorities
Matthew Stuart is interviewed by Lieutenant Detective Edward McNelley of the Boston police homicide unit in the sixth floor conference room of the Suffolk County Courthouse. Detective Peter O’Malley, Assistant District Attorney Francis O’Meara, and attorney John Perenyi are also there. Matthew tells them Chuck masterminded the robbery and Carol’s murder, and produces the diamond ring they had kept. He also says Chuck had agreed to pay him $5,000 for the Oct. 23 incident. Overnight, Jack McMahon and Janet Monteforte are also interviewed, as is Mark Stuart.
around 7 a.m.,Jan. 4,1990
Chuck jumps from the Tobin Bridge
Chuck Stuart drives to the Tobin Bridge in Chelsea, leaves a note, then jumps to his death into the Mystic River. His car is spotted shortly thereafter. Police divers locate his body about five and a half hours later.
Jan. 5,1990
The authorities identify Chuck as the prime suspect in his wife’s death and exonerate Willie Bennett
District Attorney Newman Flanagan says Stuart family members and friends have presented evidence implicating Stuart in the death of his wife. Flanagan says Bennett is no longer a suspect. Police detectives execute a search warrant at Chuck Stuart’s home in Reading in the afternoon. That night, Flynn stops by the Bennetts’ home in Mission Hill to apologize.
Jan. 6,1990
David Frank MacLean confesses to police officers
David Frank MacLean makes a statement to police officers. He acknowledges he was previously approached by Chuck and that he lied when asked by a Boston police detective about Chuck’s role in killing his wife.
10 a.m.,Jan. 9,1990
The gun used to kill Carol Stuart is found
Boston police divers and State Police divers recover the gun, which is placed into a white cooler and sent for testing. It’s matched to a gun kept by owner George Kakas of Kakas Furs, Chuck’s employer on Newbury Street. Kakas had kept the gun on the premises in the event of a robbery.
Oct. 5,1990
Willie is found guilty in the Brookline robbery
A jury finds Willie Bennett guilty in the Brookline video store robbery case. A few days later, he is sentenced to 12 to 25 years in prison.
Sept. 26,1991
Matthew and Jack are indicted
Matthew Stuart is indicted. Jack McMahon is also indicted. The grand jury interviews its last witnesses and is closed. Willie Bennett is officially cleared.
November1992
Matthew Stuart and Jack McMahon plead guilty
Matthew Stuart pleads guilty to multiple charges tied to the planned insurance scam. Jack McMahon, in a separate case, pleads guilty to accessory after the fact of murder, unlawful possession of a firearm, conspiracy to impede and obstruct justice, and concealing stolen property.
2011
Matthew Stuart dies
Matthew Stuart dies of an overdose in a Cambridge shelter.
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