Jessie Rossman Forest Headshot version 2


Legal Director



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Jessie Rossman has worked at the ACLU of Massachusetts since June 2013. She has extensive trial and appellate advocacy experience in both state and federal courts litigating on a broad range of civil rights and civil liberties issues, including in the areas of privacy and technology, reproductive rights, access to medication for opioid use disorder, criminal legal reform and government transparency.

Before joining the ACLU of Massachusetts, Rossman served as a law clerk to Judge Raymond C. Fisher of the U.S. Court of Appeals for the Ninth Circuit. She also worked as a staff attorney at the ACLU of Michigan and as a litigation fellow at the Natural Resources Defense Council. Jessie has a law degree from Harvard Law School and a bachelor's degree from Yale University.

Since joining the ACLU of Massachusetts, representative matters Jessie has worked on include:

  • Represented two civil rights activists in their successful challenge to the application of the Massachusetts Wiretap Statute against people who exercise their right to secretly record police officers performing their duties in public spaces. Briefed and argued the case before both the District Court and the First Circuit, resulting in the first appellate decision expressly confirming that the First Amendment protects the right to secretly record police officers performing their duties in public spaces. Martin v. Rollins, 982 F.3d 813 (1st Cir. 2020); 380 F. Supp. 3d 169 (D. Mass 2019), summary and materials available here.
  • Represented criminal defendant in federal civil rights action to require House of Correction to provide medication for opioid use disorder (MOUD) during period of incarcerated. Briefed and argued successful preliminary injunction motion, resulting in what is believed to be the first of its kind ruling that MOUD must be provided because denial of MOUD would likely violate the 8th Amendment and Americans with Disabilities Act. Pesce v. Coppinger, 355 F. Supp. 3d 35 (D. Mass 2018), summary and materials available here.
  • Represented criminal defendants in federal civil rights actions to require Massachusetts Department of Correction and the federal Bureau of Prisons to provide medication for opioid use disorder (MOUD) during periods of incarcerated, obtaining a successful settlement on behalf of all clients. DiPierro v. Hurwitz, C.A. No. 1:19-cv-10495 (D. Mass) and Sclafani v. Mici, C.A. No. 1:19-cv-12550, summary and materials available at here and here.
  • Representing estate of Shayne Stilphen, who died in Boston Police Department (BPD) custody of an overdose, in wrongful death suit against several individual named officers and the BPD that claims the defendants denied Shayne his constitutional right to medical care and unlawfully discriminated against Shayne on the basis of his opioid use disorder in violation of the Americans with Disabilities Act. Stilphen v. City of Boston, C.A. No. 1:22-cv-11009, summary and materials available here.
  • Member of team representing estate of Madelyn Linsenmeir, who died in custody, in wrongful death suit against her custodians that claims the defendants denied Madelyn her constitutional right to medical care and unlawfully discriminated against Madelyn on the basis of her opioid use disorder in violation of the Americans with Disabilities Act. Linsenmeir v. City of Springfield, C.A. No. 3:20-cv-30036, summary and materials available here.
  • Member of teams seeking release and increased testing for people incarcerated both pre-and-post conviction in state and federal prisons during the COVID-19 pandemic, including two cases before the Massachusetts Supreme Judicial Court and one in federal court. Advocacy resulted in an SJC ruling establishing a rebuttable presumption of release for many people who were held pretrial on bail and required the state Department of Correction and the Houses of Correction to provide daily reports on COVID-19 tests and positive results, as well as the number of people released pursuant to the Court’s ruling. CPCS v. Chief Justice of the Trial Court, SJC 12926, CPCS v. Massachusetts Sheriffs’ Offices, SJC-13116, Grines v. Spaulding, C.A. No. 1:20-cv-10738, summary and materials available here and here.
  • Represented ACLU of Massachusetts in multiple federal Freedom of Information Act and Massachusetts Public Records Law litigations. Victories include successfully settling a lawsuit against the Northeastern Massachusetts Law Enforcement Council (NEMLEC) in which the Council agreed that its records are subject to the state public records law, obtaining a federal court order for the FBI to disclose several pieces of staffing and budget information for the Massachusetts Joint Terrorism Task Force, and successfully challenging the Boston Police Department’s failure to respond to multiple records requests regarding police use of force against, and surveillance of, people in Massachusetts.  ACLUM v. NEMLEC, Civ. A. No. 2014-02035, ACLUM v. FBI, C.A. No. 1:14-cv-11759, ACLUM v. City of Boston, Dckt. No. 2084-cv-01802, summary and materials available here, here, and here.
  • Member of team representing Michael Okosi in his civil rights lawsuit against a police officer who falsely claimed that Mr. Okosi hit him and made the decision to charge him with assault and battery on a police officer. Conducted direct and cross examinations as part of the three-member trial team. The jury returned a unanimous verdict in Mr. Okosi’s favor on several counts, including federal and state law claims for false arrest and false imprisonment, and a state law claim for malicious prosecution, and awarded Mr. Okosi compensatory and punitive damages. Okosi v. Roby, C.A. No. 1:21-cv-11884, summary and materials available here.
  • Member of team representing Shabazz Augustine, leading to a landmark ruling by the Supreme Judicial Court that people have a reasonable expectation of privacy in their cell site location data that is protected by Article 14 of the Massachusetts Declaration of Rights. In so doing, Massachusetts became only the second state supreme court in the country to impose a warrant requirement for CSLI more than three years before the United State Supreme Court reached a similar conclusion under the Fourth Amendment. Commonwealth v. Augustine, 467 Mass. 230 (2014), summary and materials available here.
  • Spearheaded ACLUM’s amicus advocacy on privacy and technology issues, including authoring numerous SJC amicus briefs that successfully argued for increased privacy protections against the government’s use of cell site location data, automatic license plate readers, home-trained pole cameras and tower dumps. Commonwealth v. McCarthy, 484 Mass 493 (2020); Commonwealth v. Perry, 489 Mass. 436 (2022); Commonwealth v. Mora, 485 Mass. 360 (2020); Commonwealth v. Almonor, 482 Mass. 35 (2019); Commonwealth v. Estabrook, 472 Mass. 852 (2015).