Yesterday morning, a group of protesters gathered in front of New Haven Superior Court to show their support for William Maisano at his sentencing hearing. Maisano, a retired police officer who lives in Guilford, was charged with breach of peace and threatening after sending a vaguely threatening email to Guilford school staff, and faced a potential five-year sentence after being found guilty on Oct. 11. He ultimately had his sentence commuted and reduced to two years probation.

“We know this guy, he’s a wonderful, peaceful guy,” said Jonathan Trotta, who described himself as a personal friend of Maisano’s. “I think this is kind of politically motivated, this prosecution. But we want to, you know, tell the world that he’s really a peaceful person.”

Maisano was arrested after sending an email to Guilford High School principal Julia Chaffe, in which he voiced his disapproval of gym teacher Regina Sullivan’s decision to dye a portion of hair rainbow colored in a show of solidarity with the LGBTQ community, before the school’s June 16, 2023, graduation ceremony. 

“If I see her dragging her personal politics and sexual preferences into this event there is going to be hell to pay,” Maisano wrote. “As a teacher, by law, she will be crossing the line, and so will the school by not shutting this down.”

While Maisano and his supporters have claimed that he was threatening to bring media attention to the school, school staff were concerned that his email threatened physical violence. Maisano was first investigated by Guilford police on suspicion of breach of peace, a misdemeanor, but officers closed the investigation after a conversation with him.

A few days after the graduation ceremony, however, Sullivan filed another report leading to Maisano’s June 30 arrest for breach of peace, with state prosecutors later charging him with threatening, a felony charge that could have landed him up to five years in prison.

“There’s just no way you can elevate the expression ‘hell to pay’ into some kind of valid threat,” said Trotta before Maisano’s sentencing. “I don’t think any reasonable person would consider that to be a valid threat.”

Trotta was one of about a half dozen protesters who showed up outside of court in support of Maisano. Kathleen Walsh, organizer of the Facebook group Blue Lives Matter Connecticut, said she organized the protest via social media after hearing about Maisano’s story. 

“This could happen to anyone,” said Walsh. “That’s why Billy’s standing firm.”

She said that around 50 people signed up for the event, but thought a combination of frigid weather and the sentencing’s Wednesday morning start time may have decreased turnout. Another protester, Elaina Starr, said she took time off from her job and took the drive “on a really, cold windy morning” because of her “strong values and views on being able to exercise our First Amendment rights to free speech plainly and simply.”

While his supporters agreed that the email may have been poorly worded, they all shared the belief that the charges against him represented an infringement upon his right to free speech. Trotta shared his belief that the case should concern more than just people who share Maisano’s views.

“I think no matter what side of the political spectrum we’re on, I think this is unacceptable for anyone, for any parent, and that’s one of the terrifying elements of this is the parents are silenced,” said Trotta. “They’re afraid of retribution like this.”

As sentencing loomed closer, more people showed up in support of Maisano. By the time the pro-Maisano crowd was corralled into the courtroom, it numbered a little over a dozen people. On the other side of the benches, separated by a bailiff, were Chaffe, Sullivan and Guilford Superintendent Paul Freeman, who each gave their own pre-sentencing testimony.

Chaffe was the first to testify and proceeded to describe her history with Maisano. She said she was no stranger to Maisano, nor his emails, which she described as “erratic.”

“In the last three-and-a-half years, I’ve received many communications from Mr. Maisano, some benign, some complimentary, and some that mischaracterized me, my work, and my leadership,” said Chaffe. “On one occasion Mr. Maisano called me, ‘Paul Freeman’s lapdog’. On another, he was extolling my qualifications to be the superintendent of schools. He has also repeatedly called into question my competence and my integrity. On other occasions, he has been incredibly kind, as when my stepmother passed away and he sent me his condolences.”

Chaffe said she had never before felt threatened by him until his June 16, 2023 email. She noted the email did not “permit me to interpret the intention behind the words.” She also asserted that since Sullivan is the school’s graduation coordinator, and was present on stage during graduation, that a “threat to her on graduation day is a potential threat to many people who are on that stage.”

“I continue to be stunned that as a former police officer, Mr. Maisano refuses to understand this, or the impact that his words had,” said Chaffe. “The fear of violence happening within the school is a constant shadow that public educators confront daily.”

Chaffe noted that the email’s impact was exacerbated by the fact that just a shooting occurred at the graduation ceremony of a high school in Virginia shortly before the incident, a sentiment later echoed by both Freeman and Sullivan.

“On this day, it was especially disturbing to receive a message like this, within two weeks of a public shooting that occurred at a graduation,” said Chaffe. “Whatever the intention, Mr. Maisano’s emails sent waves of fear and hesitancy through every aspect of planning for the day. It transformed what should have been a celebration of our graduates into an afternoon of vulnerability and potential danger.”

Chaffe noted the case balanced Maisano’s First Amendment rights, describing them as a “cornerstone of freedom and democracy,” and the school official’s desire for safety.

“The responsibility indelibly linked to freedom, to this freedom, cannot be overly emphasized,” said Chaffe. “Words have power, and when wielded recklessly, they erode trust and safety.”

Chaffe concluded by saying that the fact Maisano has refused to take responsibility for his actions alarmed her, and that she would “like to see this rectified.”

Freeman spoke next and stressed the unique impact of Maisano’s emails on the school’s graduation plans. Freeman said that while the school has always had the contingency plan of holding graduation ceremonies indoors due to rain, they have never had to do so, and Maisano’s email made school officials consider the move for the first time in the 13 years he’s worked there.

“When we received Mr. Maisano’s threat, we immediately began plans to move that graduation indoors to the high school gymnasium where we would have a more controlled setting,” said Freeman. “On that morning, we began planning to make that concession not because of rain, but because of a threat that we had received.”

Freeman said that he spoke with Guilford Police after receiving the email, who assured him that Maisano promised not to be at the event, and that the police, who recognized his face, would be present to ensure the safety of the ceremony. Despite officers’ assurances, Freeman said that “those of us who were aware of the threat and took the stage that afternoon, however, did so with lumps in our throats.”

Freeman said that educators should not be faced with the stress of having to interpret such emails, or make decisions in which they must weigh “the importance of an event for our students versus the seriousness of a threat we received earlier that morning.” He shared his belief that since Maisano had shown “no evidence of responsibility or remorse,” he be punished more severely.

Sullivan was the last Guilford educator to testify. She said that the incident “has left deep scars on my sense of security and wellbeing.” She called his email “calculated,” and “an effort to cause fear and panic.” She also stressed the fact that the email was only the tip of the iceberg regarding Maisano’s interactions with her.

“He has also continued his relentless pursuit of involvement in my life,” said Sullivan. “He has filed multiple FOIA requests for records related to the Gender and Sexuality Alliance Club that I am the advisor to, the girls’ soccer team which I coach, and most recently, my union work. None of which involve him or his children.”

Sullivan said that Maisano has attended union meetings in which she’s present and “continues to insert himself into areas of my professional life where has no reasonable connection.” She said that his actions “feel obsessive, and entirely focused on opposition to who I am as a person.”

Sullivan addressed her identity as a lesbian, and spoke with disdain for the attention this incident has brought upon her sexual identity.

“I stand firm with who I am,” said Sullivan. “However, the public exposure resulting from this case has been an egregious invasion of my privacy. I have been outed in the most public and unnecessary way.”

She said the incident has “fundamentally changed how I live my life.” She spoke of the heightened vigilance she now has in public, and said that Maisano’s repeated inquiries into her professional life have made her incapable of easing her mind.

“As recently as two weeks ago, just as I was feeling like I might be able to let my guard down, I was reminded of the shadow he has cast over my life when I was made aware of yet another FOIA request,” said Sullivan. “The courts cannot allow this blatant disregard for public safety and targeted harassment to go unnoticed.”

She asked the court to “take these impacts seriously,” and ensure “measures that will keep Mr. Maisano as far away from me as possible.”

Ultimately, Maisano had his sentence suspended and was issued two years probation. Sullivan was granted a criminal restraining order against Maisano, which bars him from contacting her for the next ten years. As a parent of two children in the Guilford School District, Maisano must communicate with school officials a day in advance before attending school events. He was also ordered to pay $100 a month for the next two years, for the purpose of reimbursing fees Sullivan paid for mental health treatment after the incident. As a convicted felon, Maisano is now unable to own any firearms and must provide the state with a DNA sample.

Maisano has already filed an appeal of the sentencing. His appeal lawyer, Mario Cerame, issued a statement after the sentencing concluded.

“The issue is not whether someone could see ‘there will be hell to pay’ as a threat. The legal test is whether a reasonable person unambiguously would understand the phrase as a threat of physical violence,” read Cerame’s statement. “This case should have been dismissed.”

Prior to his sentencing and entrance to the courtroom, and during his own brief testimony before the court, Maisano said he felt “blessed.” After his sentencing, he felt the same way.

“The judge was very fair,” said Maisano. “I do feel very blessed with the people turning out today. My faith has been renewed.”

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