Matthew Rutledge, a former teacher at Miss Hall’s School in Pittsfield, Massachusetts, officially entered a not guilty plea in Berkshire Superior Court. The 64-year-old, who previously held roles as a history teacher, coach, resident adviser, and department chair, faces three counts of rape following a grand jury indictment. This court appearance marks a major win for Hilary Simon and Melissa Fares, who have spent years working to bring these allegations to light.
Per NBC News, the legal process has been long and, at times, discouraging. Back in October 2024, Berkshire District Attorney Timothy Shugrue initially announced that his office could not pursue criminal charges against Rutledge. At the time, the office cited the fact that the age of consent in Massachusetts is 16, and existing state law did not criminalize sexual relations between teachers and students if the student had reached that age.
Despite that major setback, Simon and Fares refused to let the matter rest. They collaborated with state lawmakers to support legislation that would hold individuals in positions of power accountable for such actions, regardless of the age of consent. That bill remains in process with the state legislature.
It is crazy that they had to work so hard to get this to court
While pushing for legislative change, the two survivors also pursued civil action, filing separate lawsuits against the school. Fares filed her suit in 2024, followed by Simon in 2025. The District Attorney’s office then stepped forward to help.
A team of special prosecutors and state police detectives was assigned to revisit the evidence collected by the Pittsfield police and a private law firm hired by the school. This review led to the conclusion that Rutledge had violated Massachusetts General Law, resulting in the recent indictment.
The courtroom environment was heavy with significance for the survivors. Before the hearing, Simon shared her perspective, “I am not expecting drama or resolution that day,” Simon told NBC News. “What I am expecting is that, for the first time, he will stand in a courtroom and answer to these charges. That alone matters. It is the beginning of the formal process, not the end of our work.”
Fares, who works as a journalist, echoed this sentiment. “I expect it to be fast and procedural, but also deeply emotional,” said Fares. “For the first time, I’ll be in the same room with him where he no longer has power over me. I definitely plan to let that land.”
The allegations against Rutledge date back to his time at the school, where he was known as a larger-than-life figure. Per NBC News, reports from the school indicate that he would often walk through the hallways shouting, “Make way for Mr. Wonderful.” This persona helped him establish the kind of trust often seen in grooming scenarios.
According to the Alliance for Children, grooming is a calculated process where an offender establishes trust, builds a relationship, and eventually breaks down physical boundaries. Offenders often seek positions of authority to gain easy access to vulnerable individuals, presenting themselves as community pillars or friendly mentors.
A law firm hired by Miss Hall’s School found that Rutledge had been reported for inappropriate behavior multiple times, yet the school leadership consistently failed to act. In fact, it was found that Rutledge had targeted five girls over 20 years. The report also uncovered other instances of sexual misconduct involving different former staffers at the school that stretched back as far as the 1940s.
For Fares and Simon, the journey to this point has been defined by their refusal to be silenced. Fares, now 33, alleged that Rutledge preyed on her between 2007 and 2010. Simon, 39, said the abuse occurred between 2001 and 2005. Both women stated they were 16 when the abuse began and that it continued even after they graduated.
During her testimony before the grand jury, Fares expressed a sense of relief, “There were too many moments where it felt like it might not go anywhere. So I held onto hope, but also protected myself from expecting it.
Simon noted, “What I do know is that Melissa and I were clear from Day 1 that there was never any consent,” Simon said. “We never wavered on that. Not once. And I think that consistency, that refusal to let anyone reframe what happened to us, is part of what kept this case alive.”
Although this arraignment is a significant milestone, the work of the Berkshire County District Attorney’s office is far from over. The office has stated that its investigation into Rutledge, as well as any suspected criminal conduct involving other staff members at Miss Hall’s School, is ongoing.
Published: Apr 27, 2026 09:40 am