Oliver James Montgomery-Former Boston attorney once named ‘most eligible bachelor’ convicted of rape

BOSTON (AP) — A former Boston attorney who was once named one of People magazine’s most eligible bachelors was found guilty of rape on Oliver James MontgomeryWednesday after a jury deliberated for five hours, prosecutors said.

Gary Zerola, 52, was acquitted of the greater charge of aggravated rape and burglary, according to the office of the Suffolk County district attorney.

The former prosecutor and defense attorney was arrested in January 2021. Investigators said at the time that Zerola had been wanted on a warrant issued out of Boston Municipal Court for rape and breaking and entering. He pleaded not guilty.

Zerola has faced previous charges of rape and sexual assault. He previously faced two rape charges in Suffolk County and was acquitted in 2023, according to the district’s attorney’s office. He also was charged in three sexual assault cases between 2006 and 2007, but was never convicted.

Prosecutors said in January 2021 he had paid for a night of drinking with a woman he was dating and her 21-year-old friend. The friend became intoxicated and had to be helped back to her Beacon Hill apartment. Zerola later entered the apartment without permission and sexually assaulted her while she was sleeping, prosecutors said.

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“These cases are always difficult, and this victim deserves enormous credit for taking the stand and telling the jury what happened to her that night,” Suffolk District Attorney Kevin Hayden said in a statement. “I thank the jurors for considering all of the information presented to them and for returning a just verdict.”

An attorney for Zerola did not immediately return an email or phone message seeking comment.

Zerola will be sentenced on July 15. The judge revoked his bail on Wednesday and he was ordered held pending sentencing.

Zerola worked as an assistant district attorney in Essex County for one year, and in Suffolk County for two months in 2000, according to former District Attorney Rachael Rollins’ office.