BOSTON — He broke into an elderly housing complex. Found a 76-year-old woman sleeping alone. Fought her in her own bed. Put his hands inside her. Then robbed her apartment and walked out into the night.

Harold Calligan got life in prison for it. He was never convicted of a sex crime.

Now, 23 years later, the entire Massachusetts Parole Board has voted to set him free — with mandatory sex offender conditions attached to his release. The same board that says he wasn’t convicted of a sex offense is treating him like a sex offender on the way out the door.

The Bristol County DA told the board not to release him. They overruled her. Unanimously. And nobody told the public.

Calligan was 37 years old. His victim — identified only as M.B. in the parole board’s record of decision — was 76. She lived alone in an elderly housing complex in North Attleboro.

He broke into her apartment. She woke up to find him standing in her bedroom. In the board’s own words, Calligan “fought her and put his hands down in [her] privates.”

He then took her belongings and left. She called 911 and described her attacker. Police found Calligan nearby. She identified him as the man who had just assaulted her in her home.

On January 9, 2003, a jury in Bristol Superior Court convicted him of burglary — assault on an occupant — and larceny. Not sexual assault. Not rape. Burglary. Whatever happened in that bedroom, it never made it onto the charge sheet.

The court sentenced him as a habitual offender: life in prison, plus a consecutive four-and-a-half to five-year term.

The habitual offender designation was no accident. Before the 2001 assault, Calligan had already served 12 years in prison for a prior rape conviction. He got out, and then broke into a 76-year-old woman’s apartment and did it again.

Calligan waived his first parole hearing in 2016. He was denied in 2022.

On December 2, 2025, he tried again. Five of his friends showed up to tell the board he was a changed man. Assistant District Attorney Karen O’Sullivan showed up to tell them he wasn’t.

On March 23, 2026, the board sided with the friends. The vote was unanimous.

The decision says Calligan has maintained sobriety, had no disciplinary reports in seven years, and “takes responsibility for his crimes.”

The board called that taking responsibility.

Calligan was convicted of burglary and larceny. There is no sex offense on his record. But the board’s parole conditions include mandatory sex offender requirements — the kind of supervision typically reserved for convicted rapists and child predators.

The board described what he did. They know what happened in that apartment. And then they let him out anyway — with conditions that acknowledge a crime he was never charged with.

He’ll be placed on electronic monitoring for six months. He must stay home between 10 p.m. and 6 a.m. He’ll be supervised for drugs and alcohol, barred from contacting the victim’s family, and required to attend mental health counseling and AA at least three times a week.

The decision was posted quietly on the Parole Board’s website. No announcement. No press release.

Harold Calligan is a free man.