Wealthy lawyer once named one of People Magazine's 50 most eligible bachelors is jailed for shocking sex crime

A suave Boston lawyer who was once named one of People magazine's 50 most eligible bachelors was sentenced on Monday to serve up to a decade behind bars after he was convicted of raping a woman in 2020. 

Gary Zerola, 52, who has been accused of rape by as many as a dozen women over a 25-year period, will serve five to ten years in state prison.

Last month, the disgraced attorney was convicted of raping a woman after a night of partying in November 2020.

Zerola, who had previously faced other rape charges, was acquitted of the greater charge of aggravated rape and burglary. 

Gary Zerola, 52, who was once named one of People Magazine's most eligible bachelors was sentenced on Monday to serve up to a decade behind bars after he was convicted of raping a woman in 2020

Last month, the disgraced attorney was convicted of raping a woman after a night of carousing in November 2020

In 2001, the urbane attorney was named one of People Magazine's top 50 eligible bachelors because of his dashing good looks and his work in foster care.

But since as early as 1996, Zerola has faced persistent accusations of rape in nearly identical assaults.

In November 2020, prosecutors said that the lawyer took his girlfriend and her 21-year-old friend out for a night of drinking.

He paid for the drinks, and by the end of the night, the friend had become intoxicated, prosecutors stated.

'Zerola paid the entire $2,000 bar tab and tipped staff generously while saying he planned to have a "threesome" with the two women, although they expressed no such interest,' the prosecutors wrote, according to the Boston Globe.    

In 2001, the urbane attorney was named one of People Magazine's top 50 eligible bachelors because of his dashing good looks and his work in foster care

The friend had to be helped back to her apartment in Beacon Hill, where Zerola allegedly attempted to help 'undress the victim and tuck her into bed.'

Zerola's girlfriend, however, allegedly stopped him from doing so. At this point, the prosecutors said, he sent his girlfriend home in an Uber and then returned to the victim's house alone. 

Without the victim's permission, Zerola entered her home and began having intercourse with her while she was asleep, according to prosecutors. 

Around 2 am, the victim awoke to him raping her.

At the time of the assault, the victim was only 21, and Zerola was 49- more than double her age. 

In 2016, Zerola was accused of raping a 23-year-old woman on a couch. The woman testified that the lawyer had had sex with her despite her protests. 

She further testified that he did not stop until she woke her friend, who was dating Zerola at the time. 

In 2008, two different juries found Zerola not guilty of rape and attempted rape

Read More

Ex-attorney who was once named one of People's Most Eligible Bachelors is charged with rape 

Last summer, he was acquitted of the charges after a four-day trial. 

And in 2008, two different juries found Zerola not guilty of rape and attempted rape. Additionally, the deep-pocketed lawyer had sexual assault charges dropped in Miami Beach and New Orleans. 

For at least three of the allegations against Zerola, the statute of limitations has expired, according to the Boston Globe.

Before he went into private practice, the Boston lawyer worked for a year as a prosecutor in Essex County. He also did a three-month stint as a prosecutor in Suffolk County for two months in 2000.

Zerola's victim made it clear just how traumatized she is in her impact statement, which was read by prosecutor Ian Polumbaum.

For several months after the rape, she said she 'experienced nightly recurring nightmares reliving the assault,' 25 News reported.

The assault, she stated, has led to her 'paranoia trusting men.'

'Even today I still have nightmares of someone breaking into my apartment and trying to assault me. I had never experienced a nightmare in my life before this. I’ve lost many nights of sleep,' the victim continued. 

'Every time I'm in my apartment, my door is deadbolted, and I live in constant fear that someone will enter without my permission and hurt me again.'