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 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.

The year 2004 brought Zerola a dose of gravitas to match the glitz of the People accolades, in the form of a $30,000 Boston Neighborhood Fellows award for his advocacy on behalf of foster kids. Mayor Tom Menino presented Zerola with the check at a ceremony held in honor of him and the other five award recipients. Zerola later testified that he gave his money to the Department of Social Services.

Zerola’s legal problems began February 27, according to court documents, when he met a 19-year-old woman at the Boston nightclub Light. Zerola got behind the bar himself to pour the woman a Long Island iced tea, and after last call she and a few friends headed with him to his apartment on Joy Street. Around 3 a.m. one friend left (the police report is vague as to whether the other friends did, too), but the woman was tired, and Zerola offered her the downstairs bedroom. The woman fell asleep fully clothed, only, she claims, to be awoken by Zerola. "I just want to play," she says he told her, according to a memorandum filed in court by prosecutors. After she told him no, he allegedly repeated his entreaty: "I just want to play. I just want to play. " He then allegedly raped her.

According to the prosecutor’s account, after the alleged attack the woman left Zerola’s apartment, told a friend, and then called the friend’s mother, who drove her to a Salem hospital where doctors performed a rape examination. There, police questioned the woman. A few days later, she received a voice message from Zerola that said, in part, "I have some things going on in my life that we need to talk about." Prosecutors also claim Zerola and his friends harassed the woman in the following days, with one of Zerola’s friends allegedly stopping by her house and asking her to "settle" the matter out of court. For the time being, she decided against filing charges.

In May 2004, Zerola closed on a $370,000 condo on Commercial Street in the North End. But the next month, Zerola sold the condo for one dollar to his brother, Paul Zerola, who holds both a real estate license and a law degree. Paul held the condo in a trust while Zerola took out a "declaration of homestead." Such a document protects a property from liquidation, should the owner fall into debt and the Internal Revenue Service come calling.

It appears Zerola was living beyond his means. He already had an outstanding 2002 federal tax lien of $1,432 against his new law office. But by 2005, Zerola would owe the IRS much more: $109,762. That same year, according to the Massachusetts Attorney General’s Office, Zerola dissolved One for the Kids. His money troubles weren’t over. The IRS came back in 2006, looking for an outstanding $85,697; the state wanted another $14,702. Liens were later issued against Zerola for both sums, in addition to a fifth lien, filed by the state against Zerola’s law office that year, for $19,309. On July 11, one day before the statute of limitations expired, Zerola filed a lawsuit against the West Street Grille claiming that, in 2003, the bar had overserved patrons who subsequently "attacked" him. He demanded $50,000 for the soreness, facial abrasions, and fractured right ankle he sustained, only to drop the case soon after.

Zerola did his best to keep up appearances despite his tax burdens. He bought a Porsche in the spring of 2006 and continued partying on the weekends. It was this profligacy that brought him to the attention of another young woman.
She, like the first, was 19. They spent the afternoon of August 17, 2006, shopping on Newbury Street, Zerola buying her a $450 Dolce & Gabbana leopard-print dress and $200 shoes. Later, driving back from her parents’ house in Newton, where the woman had retrieved some makeup, they passed a fender-bender on Route 9. The woman says Zerola yelled out the Porsche’s window, "Do you need a lawyer?"

That evening at Zerola’s condo, the woman met his acquaintance Jesse Bumbaca. According to Bumbaca’s later testimony, at one point, while the woman was in the bathroom, Zerola told him, "I’m going to bang this girl." (Zerola denied the allegation during the January trial.) The couple then visited two nightclubs, Saint and Mantra; Zerola snorted cocaine and swallowed Vicodins throughout the night, according to the prosecution. (Zerola denied the charge.) The woman did drugs as well.

Early the next morning, they returned to Zerola’s place, where he allegedly asked the woman to "take another Vic." She grew nervous. According to her account, Zerola then got on top of her, held down her arms, ripped off her dress, and slammed her head into a wall. She ran into the hallway naked but he caught up with her, covered her mouth, and dragged her back inside. As the alleged assault continued, Zerola said, "I just want to play," according to the prosecution. The woman alleges he let her go when he noticed blue lights flashing outside his window.

"He said, ‘I’ll take you home now,’ and told me to put on the dress," the woman testified. Some time later she ran into Zerola at a club, according to prosecutors. Touching her arm, he said he was "so sorry" for what happened, she alleges.

On November 21, 2006, Zerola was indicted for two sexual assaults: the one from that August, and the alleged 2004 incident. He posted the $50,000 bail and was awaiting trial last October when he decided to go to the Patriots-Dolphins game in Miami, in violation of the conditions of his release. There he met an 18-year-old Florida International University student at Club Mansion in South Beach, according to police reports later filed in court. They drank and then headed off to a room at the nearby Catalina Hotel, where Zerola allegedly "held her face with his hands and forced her to take an unknown amount of pills with an unknown liquid." She passed out, and when she woke up, according to police reports, "she felt pain all over her body." Zerola wa
s still with her, trying to persuade her not to leave. She managed to put on a robe, grab her cell phone, and escape. The woman called a friend on campus, who then called police. "I never had sex with her," Zerola reportedly said when the officers arrived.


Many people who know Zerola find it inconceivable that he is capable of rape. Esther Vargas, for instance, says, "The Gary I read about is not the Gary I know." The ex-girlfriend says he treated her "like a princess," never raising his hand, or voice. But neither woman testified during his first trial. In the end, the witness who convinced the jury of Zerola’s innocence was Zerola himself.
He was on his game during his time on the witness stand, precise in his answers and charismatic in his demeanor. His accuser’s story, by contrast, changed four times from the initial police report to her testimony. And Zerola’s version of what happened in the apartment was dramatically different from hers.

Under oath, Zerola said they had kissed but the victim stopped and told him she had a boyfriend. Zerola admitted he was upset, and that he "said some mean things to her." When she demanded he either drive her home or pay for a taxi, he said, "Why don’t you have your boyfriend come pick you up?"

Zerola said the struggle started after he went into the bathroom to get ready for bed and he heard a crash in the living room. The woman, he said, had smashed a $7,000 glass figurine he had purchased at an estate sale. As he tried to get her to leave, she said her boyfriend was a police officer. Zerola would regret not driving her home.

He said he walked the woman downstairs to retrieve her bag from his car, but when he saw a police cruiser pull up and heard the officer in the driver’s seat call her name, he got worried, thinking it might be her boyfriend. He went back up to his apartment. "I figured she was their problem now," Zerola said.
The jury deliberated for seven hours over two days. As the "not guilty" verdicts were read, Zerola shook with sobs. The accuser left the courtroom before the jury was dismissed.

Significant weaknesses exist in the remaining cases against Zerola. In the trial scheduled for April 7, the court will hear from the defense that the accuser in the 2004 incident took a shower after the alleged attack and did not get a rape examination until 12 hours later, and that the exam found scarce evidence of sexual assault. Should the Miami case reach trial, prosecutors must contend with an alleged victim who is unable to remember anything from the incident. (One of the charges from that night has already been dropped due to her wavering account, according to Zerola’s legal team.)

This is not to say Zerola will have the fast life back if he’s acquitted of all the charges. The Porsche is gone, the condo sold; he has paid off only three of the tax liens against him. He now lives with his brother’s family in Melrose. With his license to practice law suspended, the one-time would-be legal hotshot has had to take a job selling insurance.

Perhaps most humiliating, the man who made it his mantra to work hard and play harder can no longer play at all. Every day, Zerola must call a probation officer when he leaves for the office, and twice more during the day, the last when he returns home. Which these days is always well before the clubs close.

Additional reporting by Paul McMorrow and Paul Kix.