'Decades of pain': Now both killers of elderly Middleboro man granted parole. Why?

Amelia Stern

The Enterprise

Published May 21, 2025

A man found guilty of the 1986 murder and armed robbery of an elderly Middleboro man was granted parole after serving 38 years in prison, according to a Massachusetts Parole Board decision.

Michael Eagles, now 59, was originally sentenced to life without the possibility of parole after he beat and strangled 79-year-old Lewis Jennings to death inside the victim’s Middleboro trailer.

The highest court in Massachusetts ruled in January 2024 that mandatory life-sentencing without the possibility of parole for defendants 18 to 20 years of age at the time the crime was committed is unconstitutional, according to the Massachusetts Supreme Judicial Court's Commonwealth vs. Mattis decision.

As a result of the decision, Eagles, who was 20 years old when he committed the crime, had his sentence commuted to allow parole eligibility after 15 years.

The state parole board decided on May 14 to release Eagles to Rhode Island and ultimately back to his family, according to the Plymouth County District Attorney's Office, which opposed his release.

Eagles’ attorney could not be reached for comment at the time of this article’s publication.

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'Matured and changed': Why the MA Parole Board decided on release

According to the parole records, while in prison, Eagles recovered from substance use issues and maintained sobriety for more than three decades. After his January parole hearing, the board described Eagles as having matured and changed.

The victim’s family testified against Eagles’ release along with Plymouth County Assistant District Attorney Karen Palumbo.

“The Jennings and Villaire families have endured decades of pain due to the callous actions of Michael Eagles and his co-conspirator,” Plymouth County DA Tim Cruz said in written response to the parole board decision. “It is a fate undeserving for a man who ensured Lewis Jennings’ family would never be whole again.”

Three of the seven board members voted to deny Eagles parole, records show.

Co-defendant released in 2020 Teen killer in 1986 Middleboro murder granted parole

A 1986 Middleboro murder gets re-examined: What happened?

In July of 1986, Eagles and co-defendant Jeffrey Roberio, who was also convicted of first-degree murder and armed robbery, went to a Middleboro resident’s trailer to steal money, according to court documents.

The next day, the resident of the trailer, 79-year-old Lewis Jennings, was discovered dead on his living room floor. He was badly beaten and had a pillowcase knotted around his neck, court documents said.

According to the DA's office, an autopsy showed Jennings' spine had been fractured, an elbow had been dislocated, and several ribs and neck bones had been fractured. The medical examiner found Jennings died from multiple blunt force injuries and strangulation.

At his original trial, Eagles said he was only acting as Roberio’s lookout to feed his addiction. During the attempted robbery, Eagles said he heard a noise and when he entered the trailer, saw Jennings with a shotgun pointed at Roberio. He said he tackled Jennings and participated in the assault, but placed the majority of the blame on Roberio, according to court documents.

'Cruel and unusual': 17- and 20-year-olds committed to life without possibility of parole

Eagles and Roberio were both sentenced to life without the possibility of parole for the first-degree murder charges.

Roberio became eligible for parole in 2013 when the SJC decided that life without parole was a cruel and unusual punishment for minors.

Robario, who was 17 years old at the time of the crime, was released from prison in 2020 and committed to a residential rehabilitation program.

How many other inmates have been released?

As of April 16, 2025, 37 of 209 incarcerated individuals affected by the SJC decision had parole hearings, of which 11 were granted parole, Deputy General Counsel of the Massachusetts Parole Board Andrew S. Doherty said. Five of those individuals have already been released from incarceration.

THE ENTERPRISE