LUCAS WILLARD: WAMC Berkshire Bureau Chief Josh Landes has been covering this story since the beginning, and he joins us now. Hello Josh.
JOSH LANDES: Hello Lucas.
Bring us up to speed. Who is Matthew Rutledge, and how does he play into the larger story about sexual predation at Miss Hall’s School in Pittsfield?
Back in the spring of 2024, graduates of the elite all-girls boarding school came forward with allegations that the long-tenured teacher had groomed and sexually assaulted them while they were students at Miss Hall’s. The two former students who chose to come forward to share their experiences publicly were Melissa Fares and Hilary Simon, whose lawsuit against the school and Rutledge brought this story of decades-long abuse to light. Stories of sexual misconduct at private schools like Miss Hall’s are unfortunately common, and when I dug into the culture around student-teacher relationships at the school, I found allegations of Rutledge’s brazen behavior toward the young women in his care. Bethany Whitney went to school at the same time as Fares and Simon, and told me in 2024 just how obvious Rutledge’s misconduct was to her back in the late 00s:
“We had study hall every night from 6 to 9 p.m., and one night, it was around the end of study hall, and me and my friend went into his classroom to go get something. And when we walked in, he was sitting there – he was sitting in a chair, and he had his legs up on a table – and [the student's] legs were laying over his legs. And when we walked in, he did not even react. He didn't even react at all. Neither them reacted. So we had to just go into the classroom, grab whatever we needed and leave, and then me and my friend, obviously, as soon as we walked out of the room were like, that was weird. But that's the thing, is that he was so comfortable with this, and for her to not even react, he must have been really putting it into her head, this is OK, this is OK. See, they didn't even- See, everything's fine.”
My investigation into decades of sexual misconduct at Miss Hall’s – which was entirely contingent on the incredible bravery of survivors and former students speaking up – showed that this kind of misconduct from teachers – including Rutledge and many others – was allegedly part of the school’s culture for many, many years, and was allegedly actively covered up by administrators at the school. An independent investigation by an outside law firm backed up the graduates’ accounts and my reporting in the summer of 2025, which Rutledge survivor Fares told me at the time only underscored how deep the school’s choices to suppress the misconduct hurt those most injured by it:
“I think what's especially hard for me to come to terms with is that so much of this failure came from women, from people I thought would understand- And I don't know, I'm having a really hard time wrapping my mind around it. It feels like a deeper kind of betrayal. So much of what was shared by students was just dismissed by faculty and staff as mere gossip, and it's extremely belittling and deeply wrong. And I think there's such an irony here that's impossible to ignore, which is that at Miss Hall’s, we were taught to use our voices to advocate for ourselves, to have agency, to feel and be empowered- But when we, all of these girls tried to do exactly that, when they reported inappropriate or suspicious behavior, they were totally shut down. They were literally told, go to your room, write a letter of apology, they were told, you made this up. So over and over again, we were punished for speaking up and silenced and disempowered.”
Miss Hall’s board of trustees controversially chose to stand by leaders like head of school Julia Heaton and Board President Nancy Ault after the investigation’s findings were made public, despite the report indicating they failed to respond to claims of sexual misconduct by Rutledge and other teachers.
I’ll say here that I’ve reached out to Miss Hall’s for a comment on this story and have not heard back.
News of Rutledge’s indictment two years after his conduct was brought into the public eye definitely marks a major development in this story.
Why wasn’t there legal action taken sooner by local law enforcement?
At the time that Simon and Fares’s lawsuit and allegations appeared, Berkshire District Attorney Timothy Shugrue claimed a loophole around age of consent laws in Massachusetts prevented him from taking action and that technically Rutledge had not engaged in criminal conduct. Fares did not accept that explanation, and gave her take on Shugrue’s stance during a hearing in the Massachusetts State House connected to a legislative effort to fill that gap in state law back in June 2025:
“Last October, I received a message from a reporter telling me that the man who had groomed and sexually abused me as a teenager would not face criminal charges. According to a press release from the DA’s office, while the behavior was troubling, it was not illegal. I had reported rape. I had told my story to law enforcement in Massachusetts twice, but they maintained they were constrained from pursuing criminal charges. Rape doesn't always involve a violent attack by a stranger in a dark alley. It can also take the form of a trusted authority figure, like a teacher coercing a student behind closed doors in a classroom closet.”
According to the DA’s office, a team of special prosecutors and the Berkshire State Police Detective Unit were assigned to the Rutledge case in late 2024, taking over from the Pittsfield Police Department’s investigation. The aforementioned independent investigation and the DA Office’s findings – along with more testimony from Simon and Fares – led up to Rutledge being indicted by a grand jury this week.
You’ve spoken with both of those survivors this morning- what are their reactions to the indictment?
Simon told me that news of Rutledge being indicted on three counts of rape felt like decades of pain and misjustice were finally being acknowledged by a system that had failed to protect her and other survivors for so long:
“For the first time today, I feel like the criminal justice system in the Berkshires is finally saying, we see what happens, we believe you, and now we're going to do something about it. It doesn't undo what he did to us, it doesn't undo what he did to the other survivors, and nothing can ever do that. But this is a step in the right direction, and for a very long time it felt like it would never come.”
Fares told me the charges against Rutledge are a clear turning point in a long and agonizing journey:
“What infuriates me is I'm sure that not all survivors who come forward will have this moment and this kind of justice, but I still think, regardless, it's so important to for yourself, say the truth and hear the truth and have it be received and hopefully believed- But most of all, just believed by yourself and really felt by yourself.”
What happens next?
The Berkshire State Police Detective Unit’s investigation into the situation is ongoing, and a tip line for others who may have experienced abuse at the hands of Rutledge will be active starting this afternoon.
WAMC Berkshire Bureau Chief Josh Landes. Thank you.
Thank you, Lucas.
