The Massachusetts Parole Board remains concerned about a former Worcester gang leader seeking release from prison after he continues to claim a murder was “accidental despite two persons being shot in their heads.”
On March 12, 1999, James Freeman III was convicted of first-degree murder for the death of Teofila Matos (Ledesma) after a jury trial in Worcester County Superior Court. He was sentenced to life in prison without the possibility of parole.
However, in January 2024, the Supreme Judicial Court ruled in Commonwealth v. Mattis that sentencing people, ages 18 through 20 at the time of their offense, to life without the possibility of parole was unconstitutional and amounted to “cruel and unusual punishment.”
Massachusetts was the first state in the country to transform the law, experts said.
“Essentially, the brains of what we are calling ‘late adolescents’ or ‘emerging adults’ function very much like juveniles,” Northampton attorney Paul Rudof, one of the lawyers who successfully challenged life sentences for individuals aged 18 to 20, told The Republican.
There were 210 cases that fell into the Mattis decision across Massachusetts, including Freeman.
He went in front of the parole board for the first time on Aug. 14, 2025.
During the hearing, the parole board talked about what happened the evening of Oct. 4, 1994 when 19-year-old Freeman shot and killed 50-year-old Matos in the kitchen of her apartment in Worcester. Her husband, who was also present, was shot near his left eye but survived.
Freeman, the leader of the Vice Lords gang, met up with several other men and discussed committing a robbery to get money and drugs. Two of the men went to get masks to use in the robbery. Freeman went to his girlfriend’s home and returned with two guns.
When the men got to the apartment, they kicked in the front door of a downstairs apartment. After searching the apartment and finding nothing, the men went to the second-floor apartment where Matos and her husband lived.
Freeman held both victims at gunpoint in the kitchen, while telling the others what to do and where to search, according to the parole board. Freeman then shot both victims in the head.
Freeman buried the murder weapon with his girlfriend, Luz Maria Torres Rondeau, according to The Boston Globe in 1999.
While awaiting trial, Rondeau told Worcester Police she knew about Freeman’s role in the killing and led them to the gun, the news outlet reported.
But the gang began to threaten her and she started making plans to move out of Worcester.
“Every time she’d get a job, the gang would come and harass her,” a relative told the Globe. “It was a problem.”
The day before she was expected to testify, Rondeau was shot and killed as she lay sleeping next to her 3-year-old daughter, the Globe reported. Muhammad Sahin, 22, a “follower” of the Vice Lords, was charged in connection with her murder.
Freeman had offered Sahin $10,000 for the killing, the news outlet reported.
The parole board stated it takes into account Freeman’s entire “significant criminal history.”
Still, the parole board recognized that Freeman began engaging in rehabilitative programming more than 10 years ago and has been steadily employed.
Assistant District Attorney Anne Kennedy of the Worcester District Attorney’s Office spoke against Freeman getting parole.
One board member voted to grant parole. However, they were out voted by the remaining members.
On Jan. 14, parole was denied with the option for another hearing to be scheduled in two years.
Overall, there were 1,436 people on parole in Massachusetts in 2025. There were also 1,208 discharges from parole.
