The Case Against Casanova

He was once one of Boston's (and People magazine's) most eligible bachelors. This month, he'll be back in court to face rape charges that have shocked his many admirers. But it turns out that with Gary Zerola, nothing was ever as it appeared.

gary zerola

Zerola at his January trial. (Photograph by AP/bizayehu tesfaye, pool)

Gary Zerola is a good-looking man. He is 36 and fit, his olive skin taut against high cheekbones. In court he wears well-tailored suits and parts his short black hair to the left; when he has modeled summer fashions for the Boston Globe or auctioned a date with himself at a benefit, his look has been more leisured, his hair less primped. Since his days at Suffolk Law, he’s been a fixture on the club circuit, often with a younger woman on his arm. Mentions in the Herald‘s Inside Track have only furthered his renown, like the time it covered his defense of New England Cable News weatherman Joe Joyce after Joyce was charged with pot possession and trying to sell fake Jimmy Buffett tickets to undercover cops (the latter charge was eventually dismissed). Zerola has also made the gossip columns in connection with his charity, One for the Kids, which the former foster child—and this, too, was part of the aura—founded to help children growing up without their birth parents.

It was that charitable work, in fact, that People singled out in naming Zerola one of “America’s Top 50 Bachelors” in 2001, alongside Ben Affleck, Matt Damon, and Josh Hartnett. But for all the other attributes mentioned in the piece—Zerola’s industriousness, his sensitivity—one need only look to the photo accompanying it, and to Zerola’s eyes, for the real reason for his inclusion. Dark yet expressive, with a quiet mourning all their own, Zerola’s eyes are his best feature. Indeed, seven years after the People list, the woman who took the stand this winter to accuse Zerola of sexually assaulting her nonetheless said they were “the nicest…I have ever seen on a man.”

This month Zerola will stand trial in Suffolk Superior Court on a second set of sexual assault charges. There is a third accusation of sexual assault, in Miami, which is scheduled to go to trial in May. What the accusers have in common is that all are very young, 18 or 19 at the time they met him, and say Zerola first wooed them at clubs. Boston magazine has found reference in court documents to prosecutors’ allegations of a fourth incident, involving a young woman who claims her friends had to whisk her away from Zerola after he allegedly drugged her, though no charges were ever brought.

In January, Zerola beat his first assault charge. His attorney’s success in excluding evidence of the other alleged assaults from the record was key, but more so was the contradictory and occasionally giggling testimony that the alleged victim, a UMass Amherst student, gave during her three days on the stand. In this month’s trial, prosecutors will once again have to overcome flaws in their case, and Zerola, again, will have his charm and, yes, good looks to deploy in his defense. But whatever happens to Gary Zerola, alleged perpetrator, the trio of cases has added a sordid chapter to the gauzy story of Gary Zerola, playboy. Which—though few of his many admirers ever knew it—had already narrowly escaped other potentially unhappy endings.


Zerola spent each recess of the five-day trial in January greeting more than 15 friends and family members. He conducted himself the way a funeral director might: long embraces, hushed reassurances, the occasional sad smile, and, at one point, a kiss planted on the head of a woman sitting in the front row. On the stand, though, he was more the gadabout, talking freely about lavish spending in nightclubs and clothing shops, about routinely picking up bar and restaurant tabs for friends. His attorney, Janice Bassil, asked him why he consorted with younger women. Zerola’s answer couldn’t have been more direct: “Because I was single.”

But when Bassil asked about his childhood, Zerola choked up.

“Are you nervous, Gary?”

A long pause. “Yes.”

Zerola, the youngest child in a family of three brothers and four sisters, grew up in Lynn and started bouncing in and out of foster homes at age two. An ex-girlfriend says Zerola’s mother struggled with drugs and alcohol; Zerola (who declined to comment for this article) once told an interviewer that his father was a “nonfactor.” The ex-girlfriend, asking not to be identified, writes via e-mail: “When your own mom abandons you…so you can constantly be reminded that she chose other men and booze and drugs over you, something breaks. Something really breaks inside and it can never be fixed.” Esther Vargas, a friend and former foster child herself, remembers Zerola’s intellect and polite, even innocent, manner. “He kept himself clean and, yes, he was handsome…. He had that charm about him that is still evident today.”

When he was 12, Zerola was sent to live with Robert and Mildred Bowes in Lynn. Robert Bowes, an attorney, would not comment for this story, but in a 1998 interview Zerola referred to him as “my dad.” High school was not a tranquil period for Zerola, though. He was a marginal student at Lynn Vocational Technical Institute, where he often seemed angry and cut his share of classes. But he managed to graduate on time, in 1989. Recalling her former pupil, the word that English teacher Helen Breen returns to frequently is “potential.”

It was at Suffolk University that Zerola came into his own. He majored in communications and wrote for the student newspaper, but after earning his bachelor’s in 1994, he opted to pursue a J.D., in part to honor his foster father. He stayed on at Suffolk for his studies, using his participation in the school’s mock-trial team to hone the rhetorical gifts that would later benefit him both inside and outside the courtroom. Between classes, he worked shifts at the West Street Grille to make money, most of which he seemed to spend in other nightspots; an inveterate club hound, he got to know even the bar backs at watering holes throughout Boston. A law school classmate describes Zerola as someone who “tried to schmooze everybody.” It worked: He was popular among his classmates, who elected him commencement speaker when they graduated in 1998. Zerola delivered a “very good” speech, Dean John E. Fenton recalls.

The next year, Zerola landed a job as a prosecutor with the Essex County District Attorney’s Office. That November he incorporated his nonprofit, One for the Kids, and by the end of the year, working as its only officer, had raised more than $9,700 to buy coats and Christmas gifts for foster children. One for the Kids was obviously important to Zerola. He talked about it, and his own story, all the time. One lawyer, though, says it seemed a means of ingratiating himself with others, of gaining their sympathy. Or, if nothing else, of making sure they knew what he had overcome, the lawyer says.

In spring 1999, Zerola approached administrators at Lynn Vocational Technical Institute and asked if he could deliver that year’s commencement speech. Though the request was unconventional, Zerola didn’t disappoint. He called on the last kid in the alphabet and had him take the first seat, saying his own name had always put him at the end of the line. He talked about overcoming the odds stacked against him, and relying on the wisdom of elders.

Teachers called it the best commencement address they’d heard at Lynn Vocational. Students crowded around him afterward. The speech’s high point—which had brought thunderous applause—was when Zerola told the students, “If you knock on the door of opportunity and no one answers, knock it down.”


The following year Zerola moved on to a more prestigious job as an assistant DA in Suffolk County. But he hadn’t been there long before he was accused of abusing his new clout. When a friend from law school, Vincent J. Froio Jr., was arrested in August 2000 for ransacking an ex-girlfriend’s apartment and threatening her life, Zerola appeared at the police station on Froio’s behalf. Later, he reportedly sat in on Froio’s court hearing, in defiance of his superiors’ orders. (Froio could not be reached for comment.) After that, District Attorney Ralph C. Martin asked Zerola to step down.

“Vinny looked to Gary like a brother,” Zerola’s ex-girlfriend says. “On more than one occasion I witnessed Gary telling Vinny that he would always be there for him….He would have never left Vinny to fend for himself, even if it meant losing his job.”

In many ways, the setback seemed to free up Zerola for bigger things. He worked in private practice, and, in 2001, heard from the editors of People about their plans to enshrine him in their Most Eligible Bachelors list. Zerola did not, it can be said, shelter himself from the storm of publicity that followed. By 2002, he had appeared on episodes of the syndicated shows Judge Hatchett and Power of Attorney. He was receiving letters from single women across the country, one friend says. Some included nude photos.

That April, Zerola set up his own practice at 101 Tremont Street. In the handwritten note he filed with the Secretary of the Commonwealth’s Office to register his new enterprise, he indicated he’d be taking on pretty much everything: criminal, civil, family law, debt collection. But one of his first acts of business fell under a slightly different heading. In a filing with the state, he was listed as the registered agent for Bravo Productions LLC, a company helmed by the nightclub maven Louis Delpedio, whose holdings include a share of the Roxy. Though no annual reports have been filed since Bravo’s inception, it maintains an “active” business status with the state for the licensing, selling, and promoting of exotic dances and shows.