PITTSFIELD, Mass. — The two women who led the charge to expose sexual abuse at a posh Massachusetts boarding and day school for girls say they will be in the courtroom Wednesday when the former teacher accused of raping them goes before a judge for the first time.
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Matthew Rutledge, who is accused of grooming several Miss Hall’s School students for sex during his 30-plus-year career at the school, was indicted by a grand jury last month based on testimony from Hilary Simon and Melissa Fares.
Simon, who is a lawyer, said before the arraignment at Berkshire Superior Court that this was a “procedural step” during which Rutledge likely would, as most defendants in his position do, plead not guilty to one count of rape in connection with her and two counts of rape in connection with Fares.
“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 echoed Simon.
“I expect it to be fast and procedural, but also deeply emotional,” said Fares, who is a journalist. “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.”
Rutledge, 64, was indicted on rape charges last month by the Berkshire County District Attorney’s Office nearly two years after Simon and Fares came forward with the sexual abuse allegations.
Fares, 33, said Rutledge preyed on her from 2007 to 2010. Simon, 39, said she was abused by him from 2001 to 2005. Both said they were 16 when the abuse began and that it continued after they graduated.
Rutledge, who records show lives in Pittsfield, Massachusetts, could not be reached for comment ahead of his arraignment.
Rutledge had been a “larger than life” figure at the school who would bellow “Make way for Mr. Wonderful” as he walked down the hallways, according to a report prepared for Miss Hall’s School after the allegations against the teacher first surfaced.
Rutledge had, at various times, served as a history teacher, coach, resident adviser and department chair, the report stated. He resigned in April 2024 after Fares alleged to the school administration that he had sexually abused and exploited her when she was a student and after she graduated.
Shortly afterward, Simon came forward with her accusations against Rutledge.
That same month, the Berkshire County District Attorney’s office, the Pittsfield Police Department, and the state Department of Children and Families all launched investigations into the allegations.
Meanwhile, a law firm hired by Miss Hall’s School to investigate the allegations against Rutledge found that he had been reported for inappropriate behavior to school leadership multiple times and that the school failed to act. It found that Rutledge had abused five girls, including Simon and Fares, over a 20-year span.
It also detailed other cases of sexual misconduct going back to the 1940s against students by other former staffers at Miss Hall’s School.
Head of School Julia Heaton issued an apology on behalf of the school and herself after the report was released.
Rutledge has not publicly commented on the allegations against him and NBC News’ repeated attempts to reach him for comment have been unsuccessful.
Berkshire District Attorney Timothy Shugrue had initially announced in October 2024 that his office could not press charges against Rutledge.
“Massachusetts law defines the age of consent as 16,” Shugrue said in a statement at the time. “While the alleged behavior is profoundly troubling, it is not illegal.”
Fares and Simon refused to give up. They began working with state lawmakers to help get a bill introduced that would allow for people in positions of power, like teachers, to be held criminally responsible, even if the student has reached the age of consent. That bill is still in process with the state Legislature.
They also filed separate lawsuits against the school, Fares in 2024 and Simon in 2025.
While that was happening, the DA’s office assigned a team of special prosecutors and state police detectives to revisit the evidence collected by the Pittsfield police and by the school’s law firm and concluded that Rutledge had “violated Massachusetts General Law.”
Thus far, the DA’s office has not provided any further details about the evidence but said its investigation into Rutledge “as well as any suspected criminal conduct of other staff members at Miss Hall’s School” is ongoing.
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