In Connecticut, saying there would be 'hell to pay' in an email will get you arrested with threat of jail

GUILFORD, CT - By now, we have read ad nauseum about cases where individuals commit actual crimes…crimes like assault, robbery, rape, and even manslaughter…and where those cases are either dismissed or not prosecuted in the first place. 

This brings us to the small coastal town of Guilford, Connecticut, which has just over 22,000 people and is located in the south-central portion of the state. 

In 2023, a former police officer, board of education candidate, and Guilford resident, William Maisano, emailed high school principal Julia Chaffe advising her that “there will be hell to pay” if the school permitted a teacher, Regina Sullivan, to dye her hair rainbow colors to celebrate LGBGTAQ pride during the 2023 high school graduation, according to Inside Investigator. 

The Guilford Police Department was notified of the alleged “threatening” email, and the incident was closed the same day, according to police records. Sometime over the ensuing few days, “someone” caught wind of the incident, and a second investigation was started. This resulted in the arrest of Maisano. 

The original report, filed by Sgt. Martina Jakoberl of the Guilford PD did not specifically identify a complainant. In her report, Jakoberl stated the school only wished to have Maisano spoken to because they “were concerned” about the language in the email. 

In her report, Jakoberl said she contacted Maisano to get his side of the story and to ask about the intent of the email, specifically asking him if he intended to harm anyone. The report said Maisano said he was “not interested in hurting anyone and would never do that.” He said he was concerned about the political statement that would detract from the seniors graduating that day. Maisano also said he would not be going to the graduation and would not disrupt the event. 

Jakoberl explained to Maisano that “due to the ever-increasing threats against public events, it was important” that he clarify his words for the school. She also said, “that language in emails, letters, and text are up to the person receiving them.” [emphasis added] 

After she spoke with Maisano, Chaffe forwarded another email to the school resource officer, Officer Gingras from Maisano, in which he explained his “phrasing was meant as a statement that if she [Sullivan] were allowed to make graduation about herself, then [Maisano] would respond. Not with violence but with media exposure.” 

Several days later, a second case was opened, and this one saw Maisano arrested on a Second-Degree Breach of Peace (53a181) for the alleged “threat.” The second case was instituted on June 30, 2023, by Regina Sullivan, the teacher who was the subject of Maisano’s email to the school principal, and was investigated by an officer, Salvatore Nesci of the Guilford Police Department. 

Sullivan taught at Guilford Public Schools for 23 years and is chair of the Physical Education and Health Department. She is also (tellingly) the president of the teacher’s union. The arrest warrant affidavit notes that she is a “lesbian female” who is the school advisor to the Gender and Sexualities Alliance Club, or GSA for short. The affidavit explained that GSA “have emerged as vehicles for deep social change related to racial, gender, and educational justice.” In other words, it is a far-left progressive organization. 

Sullivan told Nesci that she’s had negative interactions with Maisano over the years, and he was “vehemently and vocally opposed [to] LGBTQ+ curriculum, instruction, visual aids, and lifestyle.” 

Sullivan spoke of an incident at a local Dunkin Donuts when Moisano was running for the school board. He allegedly  made some comments as she entered the building. Maisano is alleged to have made a comment to her that caused her to become “confused and embarrassed.” 

On April 25, 2023, just weeks before the email was sent, Sullivan attended a meeting as a union representative where a parent complained to the principal about a book that had been assigned to her students. The parent was displeased with the book’s content and requested a meeting with the principal and the teacher. The parent invited Maisano to attend the meeting. Sullivan said Maisano was “sarcastic and dismissive of her and objected to her presence” at the meeting because it wasn’t a union matter. 

Sullivan further complained that Maisano had filed several FOIA requests for information regarding the GSA's fundraising activities for Pride Month. The affidavit further confirmed that Sullivan did express her personal political beliefs at the graduation ceremony by dying her hair in the colors of the rainbow. 

The affidavit claimed that the “threatening undertone and strong language” in the email was “ominous.” Nesci said that Maisano’s status as a retired police officer should have made him realize that “his word choice would cause inconvenience, annoyance, alarm, and panic.” He took it further by claiming that “violence and threats against members of the LGBTQ+ community and public institutions like schools appears to be on the rise.” 

It appears clear that Sullivan’s complaint was retaliation for Maisano’s FOIA requests. The fact the initial complaint was cleared with no action, yet a second investigation was opened and resulted in an arrest smacks of political intervention in the case. 

According to Inside Investigator, Moisano is facing up to five years in prison after Connecticut prosecutors added a charge of Threatening in the Second Degree (53a-62), using the section of the statute that makes it a Class D felony because the “threat” occurred in a public school. 

Maisano underwent a jury trial and refused a plea deal to reduce the charges. A six-member jury found him guilty on October 11, 2024. 

The case has caught the attention of Connecticut free speech attorney Mario Cerame, who called the conviction “absurd” while noting that the term “hell to pay” is a euphemism that could mean many things; however, it does not specifically threaten physical harm. 

‘This isn’t even a close question, this is basic First Amendment law,” Cerame said. “This cannot stand. This is not okay. It’s obvious viewpoint discrimination.” 

Inside Investigator said Cerame spoke about a 2014 case in which a man was arrested and convicted for second-degree threatening and breach of peace relative to an altercation. In that case, State v. Krijger, Watertown, Connecticut resident Stephen Krijger was arrested after a confrontation with town attorney Nicholas Kepple outside a courthouse after a zoning dispute. 

During the confrontation, Krijger told Kepple, whose son was severely injured and disabled in a car accident, that “what happened to your son is going to happen to you. I’m going to be there to watch it happen.” 

In that case, the Connecticut Supreme Court ruled that “only serious expressions of an intention to commit an act of unlawful violence are punished” while admonishing the state for not offering evidence that “a reasonable listener, familiar with the entire factual context of the defendant’s statements, would be highly likely to interpret them as communicating a genuine threat of violence rather than protected expression, however offensive and repugnant.” 

“If Kreijger came out as not a true threat, it’s very difficult for me to understand how [Maisano] could possibly be a true threat,” Cerame said. 

The United States Supreme Court has also addressed the threatening issue, issuing a 7-2 decision in Counterman v. Colorado that to establish a “true threat” that is not protected by freedom of speech, “the state must prove that the defendant had some subjective understanding of the statements’ threatening nature, based on a showing no more demanding than recklessness.” 

Maisano’s arrest sends a chilling message to any parent who might consider complaining about teachers, other school officials, or even a public official. If someone using the words “hell to pay” can be arrested and convicted for such language, where could it stop? 

Law Enforcement Today spoke to Todd Callender, an attorney, who believes Maisano got the shaft from the Guilford Police Department and the court. 

“The cops, town, and court knew there was no Articulable Reasonable Suspicion to even investigate such a broadly-worded statement–yet they sent their message, and I’m astounded that a jury even heard that case,” Callender said. “It should have been dismissed by the judge before jury selection. THAT goes to show you how horribly corrupt these institutions are and corrupted the minds are that conceived such a plan.” 

For Maisano, he remains adamant that he did nothing wrong. He told Law Enforcement Today that he believes he is being targeted for retribution by the town of Guilford and its board of education because he has a pending class action lawsuit against the Guilford Board of Education and officials within the Guilford Public Schools. . 

The suit, filed on March 14, 2024 filed by Maisano and co-plaintiffs Danielle Scarpellino and Tim Chamberlain, alleges that the Guilford Public Shools were focused on “indotrinating their children in a radical political doctrine that is inherently racist” and that the school system implied “that the parents were racist because they did not blindly accept the radical agenda that the Defendants were attempting to impose.” 

Specifically, the lawsuit alleges six causes of action: (1) retaliation in violation of the First Amendment, (2) compelled speech in violation of the First Amendment, (3) religious discrimination in violation of the First Amendment, (4) discrimination in violation of the Fourteenth Amendment’s Equal Protection Clause, (5) common-law negligence, and (6), intentional infliction of emotional distress. 

Among the allegations made in the lawsuit, the plaintiffs complain that the Guilford schools molded its curriculum to mirror the ideas promoted by Ibram X. Kendi’s 2019 book, “How to Be an Antiracist,” which pushes the idea that the only remedy to past discrimination is current and future discrimination. One of the plaintiffs also claims that one of their students, a “white, male, Christian student” was the target of discirmination, including “manufacturing…reasons to discipline” the student, including 21 separate complaints that the students “COVID mask momentarily slipped below his nose.” 

It appears clear that Maisano is being targeted because of his pending lawsuit against the Guilford Board of Education, et.al. 

Maisano was asked about the fact that the initial complaint, investigated by a Guiilford Police sergeant was closed without any action being taken, but a second case, investigated by a patrol officer, was pushed to the point of an arrest warrant being issued. 

“The officer in question, who came to Guilford from Meriden, was only on the Guilford PD for a few years. After I was arrested, he was miraculously promoted from officer to deputy chief of police,” Maisano told LET. Quid pro quo? Perhaps. 

For Maisano, his arrest and subsequent conviction stings. He served the Guilford Police Department for around 20 years until he suffered a career-ending injury during a training class. He said that when the initial arrest warrant was submitted, the judge refused to add the threatening charge. It was only after he was arrested that the prosecutor at GA-23 in New Haven added the threatening charge. 

Maisano said the jury only spent one hour in deliberations before finding him guilty. He said the jury instructions lasted longer than the actual deliberations. He believes that since it was a Friday, the jury was anxious to get out and start their weekend. His sentencing is scheduled for December 12. 

Meanwhile, Cathleen Walsh, a police advocate from Wethersfield, is organizing a rally at the New Haven courthouse on December 12 in support of Maisano. Walsh told Law Enforcement Today that she is “hoping to get a huge rally of support going” for Maisano. 

“This is so bloody wrong,” she said. “This entire thing is so dirty.” 

Walsh said there is a GiveSendGo to assist Maisano with his appeal with a goal of $6,500. 

Law Enforcement Today stands in full support of retired officer Bill Maisano and pray that he doesn’t do one second of jail time. We will keep our readers up to date on the progress of his case and subsequent appeal.