The Gayle Isleib murder was the April 30, 1996, killing of a 54-year-old Manchester, Connecticut, grandmother by her Walmart coworker Tyrone Montgomery, who shot her seven times in her own driveway after she rejected his advances and asked to be moved to a different department. Montgomery, then 25, was convicted of murder and felony murder in 1997 and sentenced to 65 years in prison.
The Coworker Who Would Not Leave Her Alone
Gayle Isleib worked in the shoe department of a Walmart in Manchester and lived with her husband, Douglas Isleib, at 863 Tolland Turnpike. Tyrone Montgomery had worked beside her in the same department for about a year.
Arrest documents and trial testimony describe Montgomery becoming infatuated with her and making sexual comments about her to the shoe department manager. When Isleib rebuffed him and started ignoring him, he grew enraged. She told him more than once to leave her alone, complained to store management about his behavior, and eventually asked to be transferred to a different department to get away from him.
Weeks of Stalking Before the Shooting
Montgomery’s behavior sharpened in the weeks before the murder. He showed up at the store on his days off just to be near her and waited in the parking lot after her shifts to try to talk to her. He told coworkers about “killing someone and not getting caught.”
Less than a week before the shooting, he pulled a BB gun on Isleib while she was giving him a ride in her car, held it against her side, and said, “See how easy it is for someone to hijack you.” He later told police it had been a joke. The day before the murder, someone spotted him near her home.
Investigators would later learn he had been planning something far more elaborate. Three handwritten notes found in his car laid out a plot to kill Douglas Isleib with an ice pick and then kidnap Gayle. He planned to disguise himself as a woman and come to the door under the pretense of returning a cake dish. A search of his car turned up women’s clothing, makeup, an ice pick, a cake dish, a knife, duct tape, latex gloves, and a can of mace. In his bedroom, police found an invoice for a book titled Hit Man and a slip of paper with Gayle Isleib’s Social Security number on it.
The Night of April 30, 1996
Isleib was coming home from her evening shift at Walmart. At about 10:50 p.m., she pulled her Jeep Cherokee into the driveway and hit the automatic garage door opener. Montgomery had followed her in a white Mitsubishi Mirage. As she sounded her car horn, he got out with a .22 caliber Norinco rifle and fired seven shots. Five of them struck her in the head. She also had defensive wounds on her left hand. She died in the driver’s seat.
Douglas Isleib heard the horn and the gunfire from inside the house, looked out, and saw Montgomery standing at the driver’s side of the Jeep. He ran back in to call 911. After Montgomery drove off, Douglas went outside and found his wife unresponsive.
How Police Tied Montgomery to the Killing
Detectives identified Montgomery as a suspect within 24 hours. Douglas Isleib recognized him as his wife’s coworker and said he was “100 percent” certain of the identification. Investigators briefly considered Douglas because he owned a small-caliber weapon of the type used, but the case turned on Montgomery quickly once coworkers described his fixation on Gayle.
The physical evidence was heavy. Ballistics testing matched seven shell casings from the crime scene and three found at Montgomery’s home to a single .22 caliber Norinco rifle. Montgomery had bought that rifle at the same Walmart where he and Isleib worked, four days before the murder. To keep the purchase off the books, he arranged for the sporting goods manager, Salvatore Cavaliere, to place a special order. The sale never made it into the store’s gun logbook, and Montgomery did not use his employee discount. Cavaliere was later charged with tampering with the paperwork, destroying evidence of the transaction, and lying to police; the disposition of those charges is not established in the available record.
A friend of Montgomery’s told investigators that about three hours before the shooting, Montgomery said he had a rifle in his trunk and was going to Isleib’s address to “do something.”
Montgomery checked into Cedarcrest Hospital the day after the murder. Police searched his impounded car on May 2, recovering the plot notes and the cache of supplies. The rifle itself was recovered months later, on August 24, 1996, in Middletown, Connecticut.
Trial, Verdict, and 65-Year Sentence
Montgomery went to trial at Hartford Superior Court over two weeks in September and October 1997. The case was largely circumstantial but broad: the ballistics match to the rifle he had purchased, the handwritten kidnap-and-murder notes, the Hit Man invoice, coworkers’ accounts of his obsession and threats, and Douglas Isleib’s eyewitness identification.
Prosecutors also called Jeremiah Lopez, a convicted thief who had shared a cell with Montgomery. Lopez testified that Montgomery confessed to the killing in detail, describing how he had bought the .22 at Walmart, followed Isleib home, and fired through the window of her Jeep, and how he had watched the husband react and the police take the notes from his car.
On October 1, 1997, the jury found Montgomery guilty of murder and felony murder. It acquitted him of a separate attempted murder charge tied to the plot against Douglas Isleib. On November 21, 1997, the court sentenced him to 60 years for the murder and felony murder counts, with a consecutive five-year sentence for using a firearm during the commission of a felony. Total: 65 years. The family was told at sentencing that he would serve the full term without possibility of release.
Appeal and Later Admission
Montgomery appealed to the Connecticut Supreme Court, which affirmed the conviction on October 17, 2000. The court found that trial prosecutors had committed a constitutional violation by introducing evidence that he ended a police interview after being read his Miranda rights, but held the error “harmless beyond a reasonable doubt” given the weight of the other evidence. Years later, Montgomery contacted the lead investigator, former Detective Paul Lombardo, and admitted he had shot Isleib.
The Lawsuit Against Walmart
In August 1997, Douglas Isleib sued Walmart in Rockville Superior Court, alleging that store management knew Montgomery was stalking and harassing his wife and did nothing to protect her. Attorneys for the family said “there were many people in that store who knew that this guy was stalking her.” The record available here does not show how the lawsuit was resolved.
The 2021 Sentence Modification Law
The case surfaced again in the Connecticut legislature in 2021. Beth Schultz, Gayle Isleib’s daughter-in-law, submitted testimony to the Judiciary Committee opposing Section 28 of House Bill 6594, which would let people convicted of felony murder petition for a sentence modification without a prosecutor’s agreement and reapply every five years if denied. Schultz told the committee that her husband, Gayle’s son, had been so traumatized by his mother’s murder that he died by suicide in April 2012, and that the law would force families to relive the case in repeated hearings.
Governor Ned Lamont signed HB 6594 in July 2021, and the sentence modification provision became Section 25 of Public Act 21-102. Judicial attorneys later concluded that as written, the law applied only to people convicted and sentenced after it took effect, which left open whether it would ever reach Montgomery’s case.