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After 30 years in prison, the man convicted of killing Cambridge mayor’s son is eligible for parole

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Cambridge Mayor E. Denise Simmons urged the Massachusetts Parole Board to keep behind bars the man who killed her son.

“Mr. Benjamin should not be released," she told the board. "Not now, not ever.”

Ernest Nate Benjamin shot and killed Anthony Simmons, in 1995. He was convicted of first-degree murder.

After 30 years in prison, Benjamin is eligible for parole. He's part of the “Mattis” cohort, a group of incarcerated individuals whose sentences are being re-evaluated after the Supreme Judicial Court’s Commonwealth v. Mattis' decision.

In the landmark split ruling, the court said it’s unconstitutional for judges to sentence anyone under the age of 21 to life in prison without the possibility of parole.

"Advancements in scientific research have confirmed what many know well through experience: the brains of emerging adults are not fully mature," the justices wrote. "Specifically, the scientific record strongly supports the contention that emerging adults have the same core neurological characteristics as juveniles have."

The decision left more than 200 people in Massachusetts eligible for parole.

On Thursday, the parole board heard Benjamin’s case in front of a packed room. Benjamin, cuffed to the chair, read his statement through tears.

He accepted “all responsibility for [his] actions” and apologized directly to the victim’s family.

“  I’d like you all to know of the remorse that I carry deep down inside for depriving you of your loved one," he said. "I'm truly sorry for what I've done to you.”

He presented himself as a reformed man and spoke about the work he has done on his mental health.

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“Had it not been for my refusal to deal with my own pain and issues that I experienced while growing up, Anthony may still be alive.” Benjamin said.

The board questioned Benjamin for nearly two hours. They asked about the day of the crime, his mental health journey, the programs he completed inside prison and his plan if he were to be released.

Multiple friends and family members also spoke on behalf of Benjamin.

When it was her time to address the board, Simmons placed a photo of her deceased son Anthony, on the table as her daughter, Jada Simmons, sat beside her.

Simmons spoke about the pain she and her family have endured since the murder.

“ He did not just kill a man. He devastated an entire family,” she said. “My daughters lost their brother. Anthony's daughter lost her father.”

Simmons disagreed with the premise that the crime was “youthful impulsivity.”

“ Mr. Benjamin was not a child when he killed my son," she said. "He was nearly 20. He was an adult.”

Simmons also took issue with Benjamin’s re-entry plan. Benjamin told the board he'd enroll in the state's re-entry programs. But Simmons questioned whether or not these types of programs are likely to exist in the future.

“We all know that we're coming into very, very hard times with significant federal budget cuts going in the very services he's counting on to provide stability and supervision may just disappear,” she said.

Benjamin’s attorney, Lisa Newman-Polk, disputed Simmons' claims about reentry programs and asked the board to remember the purpose of the Mattis decision.

“The science has progressed in understanding that young people, even at 20, are not fully developed,” she said. “Especially when someone has endured the kind of really unimaginable trauma that Nate has endured."

The board is expected to make a decision on Benjamin's parole in the next few months.

Editors Note: This post has been updated to reflect that more than 200 people in Massachusetts are eligible for parole, per new information from the state's parole board.

This article was originally published on April 18, 2025.

This segment aired on April 18, 2025.

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Stephanie Brown Producer, Agile Production Team

Stephanie Brown is a producer for WBUR's agile production team.

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