Matthew Rutledge’s attorneys argue prosecutors waited too long to bring charges and improperly presented one allegation to a grand jury.
PITTSFIELD, MA — A former private school teacher charged with raping two former students asked a Berkshire Superior Court judge Thursday to dismiss the case, arguing that Massachusetts’ statute of limitations expired before prosecutors obtained an indictment.
Matthew Rutledge, a longtime former teacher at Miss Hall’s School in Pittsfield, has pleaded not guilty to three counts of rape involving former students Melissa Fares and Hilary Simon. The women have publicly identified themselves in connection with the case. A Berkshire County grand jury indicted Rutledge in March after an investigation that prosecutors said remained open even after authorities initially declined to bring charges in 2024.
At a Nov. 12 hearing, defense attorney Ryan Schiff argued that prosecutors cannot extend the filing deadline by adding together Rutledge’s periods of travel and stays outside Massachusetts. The dispute centers on a state law that excludes certain periods when a defendant is not usually and publicly a resident of Massachusetts from the calculation of a criminal statute of limitations.
Prosecutors contend Rutledge’s repeated stays at a home he owned in New Brunswick, Canada, stopped the limitations clock for enough time to allow the charges to proceed. Assistant District Attorney Zachary Grube argued that the Canadian property was more than a vacation destination because Rutledge kept personal belongings there, paid bills associated with the property and returned regularly. Local reporting said prosecutors calculated that Rutledge spent at least 978 days at the Canadian residence during the period they consider relevant.
Schiff disputed that interpretation, arguing that Rutledge spent about 85% of his time in Massachusetts and therefore remained usually resident in the state. He said prosecutors were attempting to combine relatively brief trips over many years to extend the deadline. The defense warned that such an interpretation could significantly broaden how prosecutors calculate limitations periods when defendants travel outside Massachusetts.
The defense also challenged the handling of one of the three rape counts, arguing that prosecutors failed to give the grand jury potentially favorable information about an accuser’s earlier account. Schiff said an earlier police report described a sexual encounter without specifically recording an allegation that it was nonconsensual. Prosecutors responded that the woman had reported sexual abuse and that charging decisions can change as investigators gather additional evidence.
Fares rejected the defense characterization after the hearing, saying she has consistently maintained that the encounter was not consensual. Simon also reiterated her allegation that Rutledge abused and exploited her. Their statements remain allegations at this stage of the criminal proceedings, and Rutledge has denied the charges and pleaded not guilty.
The Berkshire District Attorney’s Office announced in March that Rutledge had been indicted following grand jury testimony from Fares and Simon. Pittsfield police began investigating allegations against him in 2024. The district attorney’s office said later that year that it could not bring charges at that time but kept the investigation open. District Attorney Timothy Shugrue subsequently assigned special prosecutors and the Berkshire State Police Detective Unit, including resources from its Unresolved Cases Unit, to continue the inquiry.
Rutledge was arraigned in April on three rape counts and released on personal recognizance with conditions, including an order not to contact the two women. His case is part of a broader investigation into alleged misconduct connected to Miss Hall’s School that has led to separate criminal charges against other former school personnel. Those defendants have also pleaded not guilty.
Judge Michael Callahan did not immediately rule on Rutledge’s dismissal request. The court is expected to address the motion by a hearing in January. Until a ruling is issued, all three rape charges remain pending and Rutledge is presumed innocent unless proven guilty in court.
Author note: Last updated November 13, 2026.