Bristol County sex offender with history of sexual deviancy including voyeurism, pornography addiction, multiple rape convictions, granted parole with conditions

NATICK — The Massachusetts Parole Board has granted parole to a man who has been serving a life sentence since 2003 for the violent burglary and sexual assault of a 76-year-old woman in an elderly housing complex in Bristol County.

According to the Board, the Parole Board voted unanimously to release Harold Calligan of North Attleborough to a Long-Term Residential Program or Community Residential Justice program. However, his release will not occur before he serves at least 12 months in minimum security and receives clearance from the District Attorney’s Office.

Calligan, now in his early 60s, was convicted in January 2003 in Bristol Superior Court of burglary (assault on an occupant) and larceny from a building. On the evening of September 22, 2001, the then-37-year-old broke into the apartment of a 76-year-old woman living alone.

According to the decision, he fought with her, sexually assaulted her by putting his hands in her privates, and then stole numerous items before fleeing. The victim called 911 and later identified Calligan, who matched her description and was found in the neighborhood.

He was sentenced to life in prison as a habitual offender, plus a consecutive term of 4½ to 5 years. Calligan waived his initial parole hearing in 2016 and was denied parole at his 2022 hearing.

Calligan has a long-standing history of sexual deviancy to include voyeurism, pornography addiction, and multiple rape convictions.

In its decision, the Board noted several positive factors, including, no disciplinary reports in the past seven years, maintained sobriety, steady employment while incarcerated, a strong support system, active participation in programming, and acceptance of responsibility for his crimes.

Five of Calligan’s friends provided testimony in support of his release. Bristol County Assistant District Attorney Karen O’Sullivan testified in opposition to parole.

The Board concluded that “Mr. Calligan has demonstrated a level of rehabilitation that would make his release compatible with the welfare of society.”

Calligan will be subject to numerous special conditions upon release, including electronic monitoring for six months, a curfew from 10 p.m. to 6 a.m. (or at the parole officer’s discretion), regular drug/alcohol testing, mandatory mental health counseling, attendance at AA meetings at least three times per week, no contact with the victim’s family, and mandatory sex offender conditions.