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.

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.

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.

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.

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.

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.

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.

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.

Bob and Kevin discuss the origins of academic freedom, the evolution of tenure, and the clash between the principles of economic security and the financial realities facing modern universities. Kevin shares his courtroom strategies, insights on judicial independence, and the broader implications of this pivotal case for the future of academia.

Is it politics? Judicial philosophy? The advocacy and skill of the lawyers involved? The likability or lack thereof of their clients? Is it something else entirely? I started this podcast to find out what other lawyers think about these issues. By talking about specific cases, strategies, verdicts, and court decisions, I hope to answer these important questions.

Or, at the least, understand the issues a bit better. If we, as lawyers and as a society, understand how the law really works, maybe we can predict the results more accurately. Or as lawyers, give our clients better legal advice. Let's figure these issues out together. Come listen to Season 4 of Legal Judgements, starting on November 15th.

Listen as they explore the dynamics of the First Amendment in the age of social media, examining whether online comments can constitute an actual threat or fall under constitutionally protected speech.

Thompson, Director of Equality and Opportunity Litigation at the Pacific Legal

Foundation, discuss the landmark case of Cedar Point Nursery vs. Hassid and

explore the intricate balance between private property rights and public

interests. What constitutes a 'taking' and how far government regulations can

go in the name of the public good?