Private school teacher dubbed ‘Mr Wonderful’ on trial for alleged rape of two students

A former Massachusetts boarding school history teacher nicknamed “Mr. Wonderful” allegedly raped two of his students.

The former Miss Hall’s School teacher, 64-year-old Matthew Rutledge, was indicted on March 24 on three counts of rape, according to a press release from the Berkshire District Attorney’s Office.

During his arraignment this past Wednesday, Rutledge came face-to-face with his two victims, Melissa Fares, 33, and Hilary Simon, 39. He allegedly preyed on Fares from 2007 to 2010 and preyed on Simon from 2001 to 2005. In each case, the abuse started when they were 16.

Private school teacher charged with r*ping two former students after Massachusetts changed its law on teacher-student relations.

Matthew Rutledge, now 64, also known as ‘Mr. Wonderful,’ taught at Miss Hall’s School for over 30 years.

Melissa Fares and Hilary Simon, both now in… pic.twitter.com/RTDYzLP7sV

— Collin Rugg (@CollinRugg) April 23, 2026

“Today I was in the same room as Matt Rutledge, and, for the first time, I held the power,” Fares said in a statement afterward. “It has taken everything in me to get here. For a long time, I was living inside trauma without fully understanding it.”

“It showed up everywhere—in my body image, in my relationship to food and alcohol, in sex and intimacy, in how I moved through the world. I put my life on hold to face it. And it was messy. I was building a life in Paris, a dream I’ve had for as long as I can remember, and I came back here to tell this story and stay close to the people who’ve held me up,” she added.

“It was over the last several years that I began piecing together the truth of what happened to me: that Matt Rutledge had used me, abused me, and raped me,” she concluded.

In her own statement, Simon revealed that she was only 15 when Rutledge allegedly began “grooming” her.

“I fought this privately for 20 years,” she said. “I have been fighting it publicly for two. Before any of this, I was just a normal person. A lawyer. A wife and a mother. A woman trying to build a life on top of something I had buried. And then Melissa Fares called. I did not know Melissa. I picked up the phone, and I told her I had been waiting for that call for 20 years.”

“Today Melissa is my sister survivor. We share a bond that is hard to put into words, forged in the worst thing that ever happened to either of us and in everything we have built together since. She is the reason I found the courage to say his name out loud. This indictment means we were believed. It means a man who preyed on teenage girls for decades is finally answering for it. He did it because he thought he could. He did it because he thought the law would protect him. It will not,” she added.

The picture painted of Rutledge differs drastically from how he liked to portray himself.

“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 NBC News.

Rutledge resigned from his post years earlier, in April 2024, when Fares first alleged to the school that he had abused her. But Berkshire District Attorney Timothy Shugrue initially abstained from prosecuting him because the state’s age of consent is 16.

Matthew S. Rutledge, former history teacher at Miss Hall’s School in #Pittsfield #Massachusetts, will not face prosecution despite allegations of sexual abuse from five women between 1992 & 2010. The Berkshire District Attorney’s office declined to prosecute due to Massachusetts’… pic.twitter.com/nMhhwJJi7Y

— True Crime Updates (@TrueCrimeUpdat) October 21, 2024

“While the alleged behavior is profoundly troubling, it is not illegal,” Shugrue said at the time.

But Fares and Simon refused to keep fighting.

“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,” NBC News notes.

Meanwhile, Shugrue’s office assigned a team of prosecutors and detectives to reexamine the evidence. They, in turn, concluded that Rutledge had “violated Massachusetts General Law.”

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