In this episode of Legal Judg(e)ments, host Bob Stetson and attorney Dan Dain, director and shareholder at Dain Torpy and author of A History of Boston, rewind the clock to examine Roberts v. City of Boston, a historic 1847 legal battle that laid the groundwork for civil rights law in the United States. Drawing on themes from his book, Dan explores how Boston’s legal and social development shaped early civil rights advocacy, setting the stage for a challenge that began with five-year-old Sarah Roberts.

Forced to walk past several white schools to attend Boston’s only “colored” school, Sarah became the center of a legal challenge brought by her father, Benjamin Roberts. With the help of Robert Morris, one of the first African American attorneys in the U.S., and abolitionist lawyer Charles Sumner, the case argued that segregation itself denied equal educational opportunity.

Bob and Dan unpack the radical legal reasoning and social climate of 19th-century Boston. They explore how Morris and Sumner argued that segregation itself harmed all students, analyze Chief Justice Lemuel Shaw’s controversial ruling, and trace the case’s influence on Plessy v. Ferguson and, nearly a century later, Brown v. Board of Education.

Tune in to understand the broader historical context of Boston’s free Black community, early civil rights activism, and how these arguments reverberated through American legal history.

America’s first utility-scale offshore wind farm didn’t just test new waters—it ignited a major legal discussion over how the United States manages its ocean resources. In this episode, host Bob Stetson speaks with Roger and Nancie Marzulla of Marzulla Law to evaluate Seafreeze Shoreside, Inc. v. U.S. Department of the Interior. The Marzullas walk through how the case was built, why standing became a defining issue, and how the shift from the Biden to Trump administrations is changing offshore-wind permitting nationwide. Their conversation also highlights why this project became the flashpoint for national debates about climate policy, environmental risk, and the future of coastal economies.

Cities across the United States are grappling with how to manage public spaces amid the rising homelessness population. In this episode of Legal Judg(e)ments, host Bob Stetson is joined by Ed Johnson of the Oregon Law Center, who represented the respondents in the case of City of Grants Pass v. Johnson, to discuss the case, which was decided by the Supreme Court. This legal battle challenged a set of ordinances in Grants Pass, Oregon, that made it unlawful for individuals to sleep outside, including in vehicles or with basic protection from the elements, such as blankets or sleeping bags.

Bob and Ed unpack the legal arguments, including the role of the Eighth Amendment’s status-versus-conduct framework, the Supreme Court’s reversal of the Ninth Circuit, and what this decision means for municipalities trying to balance public space regulation with constitutional rights.

Oklahoma made history by approving the nation’s first openly religious public charter school, sparking a constitutional clash that ended in a Supreme Court deadlock and left the broader questions about the constitutional validity of religious charter schools up in the air. The central issue: are charter schools truly public schools that need to remain secular under the Establishment Clause, or are they privately run entities entitled to equal protection under the Free Exercise Clause?

In this episode of Legal Judg(e)ments, host Bob Stetson sits down with Christopher Schandevel, Senior Counsel at Alliance Defending Freedom (ADF) and one of the attorneys representing the charter school. They break down the high-stakes legal battle of Oklahoma Statewide Charter School Board v. Drummond, discussing how the case tested the boundaries of church-state law, the role of religious freedom in publicly funded education, and the questions it leaves open for future courts to address.

Does the constitutional right to a clean and healthful environment include a stable climate system? In this episode of Legal Judg(e)ments, "Climate Change on Trial", host Bob Stetson is joined by Roger Sullivan of McGarvey Law as they analyze the landmark case of Held v. Montana, where Roger represented the plaintiffs. This legal battle involved a group of young Montanans challenging the state’s Montana Energy Policy Act (MEPA), which prohibited state agencies from considering greenhouse gas emissions and climate impacts when reviewing energy and infrastructure projects.

Bob and Roger explore the trial proceedings, including key expert testimony connecting rising carbon levels to local environmental harms. They also provide insights into what this decision could mean for the future of similar constitutional and public interest environmental cases across the country, including questions of standing, the scope of environmental rights, and how state policies may be evaluated in light of climate impacts.

Legal Judg(e)ments returns with a new season examining how the law influences policy, politics, and everyday life. Hosted by Bob Stetson, a Boston-based trial lawyer with nearly 20 years of experience, this legal podcast features in-depth conversations with litigators about cases and strategies that shape the law. Season Five tackles timely issues including immigration enforcement, climate change litigation, offshore wind regulation, laws affecting homelessness, and more.

Tune in as Legal Judg(e)ments delivers practical insight into how the law works in practice—and why it matters now.

Listen to the season trailer now and join us for the first episode on Thursday, January 15, 2026.

In this special episode of Legal Judg(e)ments, host Bob Stetson finds himself in the hot seat as guest host, and seasoned real estate attorney Eric Allon takes over the interviewer’s mic. Together, they dissect a real estate dispute with far-reaching implications: McCarthy v. Young.

The case asks a pivotal question—when is an offer to purchase a binding contract? Drawing on precedent from McCarthy v. Tobin and the twists of a modern-day easement dispute, Bob walks us through the litigation strategy that led to an appeals court victory and reshapes how Massachusetts courts may view these standard forms.

Whether you’re a lawyer, broker, buyer, or seller, this episode is a must-listen. Discover why a simple form might be the most legally dangerous piece of paper in your real estate deal—and what you can do to protect yourself.

The Massachusetts housing crisis has spotlighted local zoning laws. With housing costs soaring, the state legislature enacted the MBTA Communities Act, requiring towns to allow higher-density housing by right. But when the Attorney General tried to enforce the law, the town of Milton pushed back, leading to a major showdown in the Massachusetts Supreme Judicial Court.

In this episode of Legal Judg(e)ments, host Bob Stetson is joined by appellate attorney Kevin Martin, who represented Milton in this high-profile case. They discuss the constitutional and legal arguments at play, the court’s ruling, and what the decision means for local governance, zoning, and housing policy going forward.

Host Bob Stetson and guest trial lawyer Stephanie Taverna-Siden explore the landmark Massachusetts case Johnson v. Settino, which reshaped the legal landscape of engagement ring disputes.

For decades, courts have treated engagement rings as conditional gifts, requiring marriage to finalize ownership. The Massachusetts Supreme Judicial Court recently struck down the fault-based standard, adopting a no-fault approach: if the wedding is canceled, the ring goes back—no blame needed.

Bob and Stephanie discuss the legal history of engagement rings, the shift away from antiquated heartbalm laws, and how this ruling modernizes the law. Download a fascinating conversation on the intersection of love, contracts, and the courts.

In this episode of Legal Judg(e)ments, host Bob Stetson sits down with Andrew Dennington, a seasoned trial lawyer and partner at Conn Kavanaugh, to explore the landmark Massachusetts case Business Interiors vs. Graycor Construction. The case centers on the Prompt Pay Act, a law designed to ensure timely payments for contractors and subcontractors in large construction projects.