“It was boarding school. There was nothing else to do,” says Sam Thompson, 23, thinking back to the types of photographs that lived on her personal laptop when she was a teen. “Boarding-school boys were crazy.”
Thompson grew up in the quiet town of Kent, in western Connecticut. Her father worked as a math teacher and football coach at the nearby Kent School, an elite Episcopal boarding school whose alumni include singer Lana Del Rey and Family Guy creator Seth MacFarlane. (Some might recall the 1999 saga when longtime Kent School head of school Father Richardson Schell engaged in a letter-writing campaign against a 26-year-old MacFarlane to kill the popular new sitcom because there was a character named after his secretary.)
In 2015, Thompson, then 14, enrolled in the ninth grade at Kent. Unbeknownst to her, she soon became one of the nearly 70 under-age female students whose personal photos were allegedly stolen by Daniel Clery, 47, Kent’s network administrator in the I.T. department for more than 20 years.
“Boarding school is not a traditional school,” Gabriela Andrade, an influencer documenting her 20s in Miami and a member of Kent’s class of 2021, says in a confessional-style TikTok video that has attracted upwards of three million views since being published, on October 9. “It’s your home for those years, and the teachers and staff members are people that you trust … They are supposed to be there to protect you.”
Both Thompson and Andrade can remember exactly when they met Clery—on separate occasions, when each young woman left her laptop with him to be fixed. What they didn’t know, much less have any reason to suspect, was that Clery allegedly used those opportunities to download a piece of software on both the women’s laptops allowing him to access their photo albums at any given time. By February of last year, when an anonymous Kent employee spotted her own photo on Clery’s phone and reported it to the school, seven employees, nine students, four former employees, and 59 recent alumni, most of them women, had allegedly been victims of Clery’s cyber-attacks.
“Boarding school is not a traditional school. It’s your home for those years, and the teachers and staff members are people that you trust … They are supposed to be there to protect you.”
Jeffrey Cataldo, Kent’s associate head of school and the person who oversaw the scandal from the start, tells me that the school fired Clery and blocked his access to the school’s network as soon as they got wind of the situation. Cataldo stresses that there had been no previous complaints about Clery and that the background check performed on him before his hiring in 2000 had come back clean.
After firing Clery, “the first thing we did was notify the state police because we knew it was a crime,” says Michael Hirschfeld, Kent’s head of school. Connecticut police immediately opened an investigation and ultimately charged Clery with two counts of computer crimes in the first degree. (Clery did not respond to AIR MAIL’s requests for comment.)
Hirschfeld, 58, isn’t new to the world of boarding-school scandals. He was the head of school at the elite St. Paul’s School, in New Hampshire, which counts everyone from Cornelius Vanderbilt III to John Kerry as alumni, from 2010 until 2019, when he resigned in the wake of the school’s high-profile trial of 18-year-old Owen Labrie, who used a school computer to send a “senior salute”—a “school tradition” where seniors made sexual advances on their younger peers before graduating—to a 15-year-old female student, whom he then sexually assaulted in the attic of the school’s science building.
In addition to reporting Clery to the police, Hirschfeld hired the private consulting firm Vancord to research how exactly Clery was allegedly able to access the photos. “We very quickly put in place a managed detection-response system that ties third-party technology to our network that is monitoring all activity that goes through our network,” says Cataldo, “so that activity that appears malicious or not normal is flagged so we can respond.”
According to the Vancord report, which dates Clery’s activity to “at least” June 2019, “a software management system which Kent School deployed to support the community was abused by Dan Clery to specifically target mostly female students to find and upload photos saved on their personal computers.” The report goes on to say that Clery had “accessed numerous student accounts” in order to view their e-mails and take “photo or movie files,” and that a “review of [Clery’s] web browsing history supports unauthorized student account access and showed signs of interest in software piracy/cracking and pornography.”
Clery, meanwhile, quickly found a job as a consultant in Yale University’s Information Technology Services department. “We weren’t keeping very good tabs on [Clery],” admits Hirschfeld, who said he learned of Clery’s employment at Yale only the previous week. “We were just grateful he wasn’t here.”
“Yale did not reach out to me or to anyone else at Kent School for a reference or a review of Dan Clery’s work at Kent,” says Cataldo. “If they did call for a reference, we would not hesitate in noting that there is a criminal matter pending … and that we certainly at Kent School would never recommend him for any work involving students.” Yale did not respond to air mail’s multiple requests for comment. (Yale declined to comment on Clery.)
“In fact, I should be clear on this,” Cataldo adds. “I don’t think we would recommend him for any work.”
“We weren’t keeping very good tabs on [Daniel Clery]. We were just grateful he wasn’t here.”
In April 2023, two months after Kent fired Clery, Hirschfeld sent an e-mail to those implicated in the alleged data breach, a copy of which was obtained by AIR MAIL. “I write to inform you of a breach of trust at the School by a former employee,” the letter began.
Hirschfeld went on to say that he would keep students abreast of updates and that, in the meantime, they should feel free to reach out to him or Cataldo. “I’m very sorry that this happened,” he wrote. “Our commitment to our community extends to cyber security and data protection, and we are doing all that we can to resolve this matter and prevent it from happening again.”
Hirschfeld also assured the e-mail’s recipients that “Vancord has not found any evidence that Mr. Clery accessed or copied information related to your identity, for example your Social Security number or banking information.”
“But don’t worry! He doesn’t have your Social,” Thompson says sarcastically. “Thank God he just has pictures of me, and I don’t know what [they are].”
“We’re talking about a 30- or 40-year-old grown man transferring pictures of 14-, 15-, 16-year-old girls for his personal use,” Andrade alleges in her video. “And I promise you, the pictures he was looking for are not pictures of us on family trips. They’re other kinds of pictures.”
“There is no evidence that would confirm that he was looking for photos of a sexual nature,” Cataldo counters. “Of course, there’s a police investigation … and I am not privy to all of the information.”
Some of the victims of the alleged leak have since started a group chat to discuss their feelings about the situation, and have reached out to Hirschfeld and Cataldo with follow-up questions. According to Thompson, she and the women she knows who sent questions never heard back. “They just don’t answer,” she says. “They just ghost you.” (“I believe I responded to all telephone calls, and I responded to all e-mails, both parent and student,” Cataldo says.)
“I promise you, the pictures he was looking for were not us on family trips. They’re other kinds of pictures.”
From April 2023 until last month, Kent School shared no new information, and those involved were resigned to wait for a judge’s decision in the case. The story of Clery’s alleged crimes remained confined largely to those involved, failing to reach even recent board members or the local papers.
Then, on October 9, Cataldo sent the Kent victims an alarming update in the case: Clery had been charged with two counts of computer crimes, both felonies, and a hearing had been set for October 30 to determine if he’d be eligible for a rehabilitation program, which, once completed, would wipe these charges from his criminal record.
“Kent School is not arguing for or against the Accelerated Rehabilitation Program,” wrote Cataldo.
This is when Andrade decided to film her now viral video. With it came floods of alumni and their concerned parents, who were referred to Karen Lucid, the state’s “victim’s advocate” Cataldo listed as the point of contact in his e-mail.
In hindsight, Hirschfeld described the e-mail to me as “clumsy,” criticizing its implication that the school had no position on the matter and clarifying that the school stands with its students in advocating that Clery be prosecuted for his alleged crimes.
Cataldo further stated to me that he and Hirschfeld both always believed that Clery, if found guilty, “should receive the stiffest punishment because of the harm he did to students and past students here, as well as to the Kent School community.”
“However,” adds Cataldo, “my view was that I should not overly influence those impacted.”
People close to the case have suggested that Clery was never going to be eligible for accelerated rehabilitation. “We’ve heard from the state’s attorney that they’re going to pursue a felony conviction, so this guy is in pretty big trouble,” says Hirschfeld. And, indeed, at the October 30 hearing the judge decided that Cleary wasn’t eligible, and the case was moved to another jurisdiction.
Clery’s next hearing is scheduled for November 22.
“I’m not sure we would have done anything differently, other than be sharper, better communicators,” reflects Hirschfeld. “But what I did not fathom was how really harmful this was. I don’t know if I could have guessed that at the time, but people really got hurt.”
Clara Molot is Investigations Editor at AIR MAIL
