The Case Against Casanova

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 was 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.