One of Zerillo’s first major trials was a Class A Gross Sexual Assault in which two men were accused of raping a 17 year-old Freeport girl. The defense argued that this was a threesome that was consensual, which the alleged victim later regretted. After a blistering cross examination of the Freeport detective and an unraveling of the alleged victim, the jury found both men “not guilty” after two days of deliberations.
Zerillo has won or hung juries on several Gross Sexual Assault trials and other sex cases, like Unlawful Sexual Contact and so on. In one such case, the prosecutor told him it was impossible to win the case. Zerillo tried the case and hung the jury, preventing the State from convicting his client.
In October of 2008, Zerillo and Daniel Lilley represented the President and Chairman of the Board of Directors of the Eagles Club against claims of Aggravated Unlawful Gambling at the Club. The case was dismissed by the Court mid-trial after the lawyers found a discovery violation during cross-examination of the state’s expert witness.
In February of 2010, Zerillo received a full dismissal of drug trafficking charges in federal court for Matthew Meineke, a former drug trafficker who reformed his life and served honorably in Afghanistan as a decorated forward observer for his infantry unit.
In 2012 and 2013, Zerillo represented six men accused of engaging in prostitution in the infamous Kennebunk Zumba sex scandal. Alexis Wright was indicted in October 2012 on multiple charges, including engaging in prostitution out of her Zumba studio in in Kennebunk, Maine. Wright ran a prostitution business in which she videotaped her prostitution clients without their knowledge so her business partner, Mark Strong, could watch from his office. This story of prostitution, secret sex videos and a client list with more than 100 names all in the small and idyllic coastal town of Kennebunk, Maine gripped the country.
Ultimately, Zerillo resolved all his cases for his clients, but was highly critical of the media’s intense coverage of the case. He noted that the print media slowly released the names of the defendants who were Wright’s clients, casting a larger spotlight on the first names that were released. Zerillo noted that “These guys are taking an absolute beating. The state and the media have hung a flashing neon sign around their neck.” In a Vanity Fair cover story, Zerillo explained that the situation was a “whole lot of sad.” He criticized the salacious media interest in the case, along with the Maine’s intense prosecution of a minor offense. The scandal was the basis of the movie called “Let’s Get Physical.”
In 2017, Zerillo represented Anthony Sanborn, the man convicted as a teenager after a trial in 1992 of the 1989 of killing Jessica Briggs and throwing her off the Portland Pier. Sanborn was serving a 70 year sentence when the matter came before the Court on a post-conviction review in 2017.
The Sanborn defense team of Zerillo and Attorney Amy Fairfield focused their attack on the prosecutor, Pamela Ames, and her team’s use of teenagers who were street kids in Portland, Maine in the 1980s to prosecute the case. Attorney Stephen Schwartz testified under examination from Zerillo in 2017 that Ames was not interested in truthful testimony from witnesses, noting that “I was deeply concerned about the nature of what Ms. Ames was saying to me, and the risk to my client of what Ms. Ames was expecting her to testify to.”
In 2018, Zerillo achieved a dismissal of a boating manslaughter case that resulted in the death of Jeffrey Beattie on Mousam Lake in Maine of May 2016. The deceased’s brother and identical twin, Jonathan Beattie, was driving the boat and was charged with manslaughter, reckless conduct with a dangerous weapon, and operating a watercraft under the influence causing serious bodily injury or death. Zerillo brought a Motion To Suppress Evidence, arguing that the way the police obtained the blood alcohol evidence and Beattie’s own statements were unconstitutionally coercive. After a suppression hearing, Superior Court Justice John O’Neil agreed with Zerillo, suppressing Beattie’s statements and the blood alcohol test. York County dismissed the case in its entirety after the suppression order from O’Neil.
In 2018, Zerillo and Attorney John M. Burke sued the Kennebec County Jail in Augusta, Maine, for the death of Dana A. Kitchin, who died December 12, 2014, in his jail cell as a result of a ruptured spleen. Kitchin died without medical attention. Kitchin had been taken to jail for a minor offense. The Jail and other defendants settled the case for the wrongful death.
In April of 2018, Zerillo won a rare speedy trial motion to dismiss in Knox County, Maine in a possession of sexually explicit materials case. There, Zerillo used an extensive jury questionnaire at jury selection, and the State could not seat a jury in two attempts. Thereafter, Zerillo brought a speedy trial motion to dismiss, which was granted, a real rarity in Maine. Zerillo had previously won a motion to suppress his client’s statements in that case when the detective agreed on the stand that he threatened to ‘tear this house apart’ if the defendant was uncooperative.
Zerillo has also represented a number of individuals and businesses in complex "bet the house" business litigation. In 2020 and 2021, Zerillo earned two large trial verdicts in trial for his clients, each verdict which was worth multi-millions. Each involved disputes between business partners and Zerillo effectively sued for the value of the businesses. Each side was represented by able counsel, one lawyer of whom is now a judge. Zerillo prevailed in each trial.
In 2025, Zerillo suppressed all of the digital evidence in a very serious criminal case in York County. The felony case of possession of sexually explicit materials involved a Maine State Police investigation that spilled into New Hampshire. Zerillo attacked the police for violating the territorial jurisdiction. He then suppressed all the digital evidence seized in the case and his client’s confession. As a result of the suppression of evidence, the case was dismissed in its entirety.