Rutledge, 63, was indicted by a Berkshire County grand jury on three counts of rape stemming from allegations that he sexually assaulted students at the all-girls school in the 1990s.
Rutledge Defense Seeks Dismissal of Rape Charges Over Statute of Limitations
PITTSFIELD, Mass. — The Superior Court courtroom was filled on Thursday as proceedings resumed on the high-profile case against former Miss Hall's School teacher Matthew Rutledge, with the court hearing arguments on his motion to dismiss.
On Thursday, Rutledge, represented by attorney Ryan Schiff, appeared before Judge Michael Callahan to seek dismissal of all three counts, arguing that prosecutors were attempting to circumvent the statute of limitations and had failed to disclose what Schiff characterized as "highly exculpatory evidence."
More than 100 attendees filled the pews, some wearing orange carnations to show solidarity with the accusers, Melissa Fares and Hilary Simon.
As Rutledge attempted to leave the courtroom following Judge Callahan's departure, several attendees voiced their outrage, shouting "Shame," "You can't hide behind the bad law," and "We know what you did."
Judge Callahan re-entered the courtroom to condemn these outbursts and directed court officers to record their names and bar them from attending future proceedings on this case.
The nearly hour-long hearing centered on competing interpretations of the language and legislative intent behind Massachusetts' statute of limitations, particularly whether Rutledge's temporary absences from the state could extend the time prosecutors have to bring charges.
Following the hearing, state Rep. Leigh Davis, who was instrumental in passing H.4538, pointed to the Rutledge case as an example of why the legislation was needed.
The passed bill aims to prevent educator and guardian sexual misconduct and abuse of children and youth and addresses an imbalance of power between adults in positions of authority and the young people in their care.
As of July 31, 2026, the proposed amendment is in the committee of conference.
This amendment was filed by state Rep. John Lawn in an effort to eliminate the statute of limitations for civil lawsuits involving childhood sexual abuse.
Had these legislative protections been in place, the case might not be facing the same legal challenges, she said.
Davis sat alongside the accusers during the hearing and reaffirmed her commitment to standing with them, stressing that "trauma does not expire."
During the proceedings, Schiff argued that prosecutors were "cobbling together" brief out-of-state vacations over the course of approximately 17 years to extend the statute of limitations, calling the approach unprecedented in Massachusetts and nationwide.
The tolling provision reads, "any period during which the defendant is not usually, and publicly a resident within the commonwealth shall be excluded in determining the time limited."
The state, represented by Assistant District Attorney Zachary Grube and Second Assistant District Attorney Joseph Yorlano, claimed that Rutledge had resided in his Canadian home for at least 978 days during the relevant time period.
While Schiff claimed that the state's argument overlooks the word "usually" as Rutledge spent approximately 85 percent of his time in Massachusetts, therefore he "usually" lived in Massachusetts and temporary vacations outside Massachusetts did not change Rutledge's residency status.
Prosecutors countered that Rutledge's recurring stays at a second home he owned in New Brunswick, Canada, qualified as periods of residency outside Massachusetts and that a person can have multiple residences.
They also pointed to the statute's historical origins, arguing that the Legislature would have considered recurring international travel and stays at a second residence significant when the law was enacted in the 1800s.
Additionally, Rutledge's recurring stays at his Canadian residence, which he owns, were part of an established routine that would have been "publicly" known to the community. The word "publicly" was also a point of contention.
Schiff warned that the Commonwealth's interpretation could establish a precedent allowing prosecutors to use cellphone location records and other evidence to accumulate even brief trips outside Massachusetts to extend statutes of limitations.
The prosecution maintained that Rutledge's ownership of a second home and regular travel patterns distinguish the trips as residency, not occasional trips across state lines.
Schiff also argued that prosecutors withheld potentially exculpatory evidence from the grand jury regarding the third rape charge.
He claimed that the accuser did not specifically allege rape until after the district attorney's office announced that its investigation had found "no criminal conduct."
"Specifically, the Commonwealth failed to disclose that the alleged victim described her allegations against Mr. Rutledge in detail during a police interview and slated that her last "sexual encounter" with Mr. Rutledge was in 2015 but did not allege that the encounter occurred without her consent or was rape," Schiff argued.
He presented three potential scenarios of what happened: the accuser told the detective that she was raped and the detective left it out of the report, not informing District Attorney Timothy Shugrue; Shugrue knew after meeting with the detective, but still announced that no criminal conduct had occurred; or the accuser did not allege rape in 2015.
Judge Callahan added a fourth scenario, in that the accuser did not use the word "rape" but rather described an incident.
Prosecutors maintained that the accuser had previously reported sexual abuse and argued that decisions can change as investigations develop.
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Lanesborough Looks to Dissolve Baker Hill Road District
By Breanna SteeleiBerkshires Staff
LANESBOROUGH, Mass. — The Select Board is looking to move forward with dissolving the Baker Hill Road District, which is hindering the Berkshire Mall sale.
On Friday, the Select Board heard from Vice Chair Juli Baker and Chair Deborah Maynard on how Tuesday negotiations went with Cypress Equities, JMJ Holdings, town counsel, the town administrator, and state Rep. John Barrett III.
Baker said that during Tuesday's meeting, everyone agreed the goal was to have a successful sale of the mall for redevelopment as it’s in the best interest of the town.
Baker said Barrett assured them the state is willing to take the Connector Road and that the state is willing to provide grants to the town to renovate the water and sewer infrastructure, with an estimated total of $4.5 million, to facilitate the property's redevelopment.
"We have received assurances from Representative Barrett that the Commonwealth will provide the monies and will take the Connector," Baker said.
While buyer Cypress Equities saw some benefit in keeping the district, it now doesn't since the state is willing to provide the funds and renovate the infrastructure, according to Baker.
Baker said that in the meeting, Cypress Equities prefers to enter into a tax increment financing (TIF) and will add to the agreement an amount of funding for public safety services, which would have come from the district. She said Cypress said it would rather enter into one agreement with the town than two agreements with the town and the district.
Mall owner JMJ Holdings is willing to pay $350,000 to the town upon closing, Baker said.
The meeting Friday was to consider moving forward with a dissolution of the district.
"But the decision that it hinges on tonight is whether to move forward to the dissolution of the Baker Hill Road District in some manner," she said.
Baker said she has worked long and hard to see if there was another alternative to this, working closely with the district which has been "very cooperative and very helpful" in making changes.
The district had agreed to make changes to its governance and taxation; agreeing to have a cap for Cypress as well as agreeing to work to have the state take over the road, sending letters of support.
"What changed this for me is that I've always said it's important to have the special district because we get the public safety funding, and it's also important for the economic district to bring the features that an economic district brings because of what we're up against with the infrastructure problems, and the change at this point is that we have a buyer who is willing to supply that public safety money and commit to it over time, along with the TIF that the town would do, which is essential," she said.
"At this point, I feel like it's in the best interest of the town and protects the town the best in terms of a future where we can develop a mall and bring that economic benefit in. You definitely need to reduce taxes, and you cannot do that without a fully developed retail operation right there. So it's been, you know, deeply difficult decision making," Baker said.
Board members Jason Breault and Jeffery Walters agreed it was the best decision to move forward.
The mural, designed by artist Carlos Jefferson, honors the 54th Massachusetts Volunteer Infantry Regiment and the Rev. Samuel Harrison and recognizes the contributions of Black Civil War soldiers and their historical ties to Berkshire County. click for more
The festival offers students the opportunity to work alongside professional theater artists, develop communication and leadership skills, and build friendships. click for more
On Thursday, Rutledge, represented by attorney Ryan Schiff, appeared before Judge Michael Callahan to seek dismissal of all three counts, click for more