Legal Judg(e)ments

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.

Tenure is under scrutiny in one of the most significant cases in higher education. In this episode of Legal Judg(e)ments, host Bob Stetson discusses the landmark case Wortis v. Trustees of Tufts University with guest Kevin Petrs, Senior Partner at Fox Rothschild, and the attorney representing a group of Tufts professors challenging the university's compensation and lab policies.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.

In this episode of Legal Judg(e)ments, host Bob Stetson is joined by attorney Christian Kiely to talk about a groundbreaking defamation case that explores the murky intersection of true crime storytelling and legal accountability. When Netflix’s documentary on the college admissions scandal painted an allegedly misleading portrait of John and Johnny Wilson, the family fought back, suing the media giant for defamation. Christian Kiely, who represents the Wilsons, discusses this high-stakes litigation’s legal strategies and implications. From the role of selective editing to the responsibilities of filmmakers in portraying real-life events, Bob and Christian discuss how the portrayal of facts can shape public perception and potentially harm reputations. 

In this episode of Legal Judg(e)ments, host Bob Stetson sits down with attorney Pat Tinsley to discuss the complexities of federalism and local governance through the lens of a landmark tobacco regulation case in Massachusetts. Pat, who represented the retailers challenging Brookline, MA’s unique tobacco law, shares insights into the statutory interpretation and the ongoing debate over local versus state authority. From the philosophical underpinnings of federalism to the practical implications for businesses and communities, this episode explores how one town’s attempt to phase out tobacco sales has sparked a broader conversation about the limits of local power and the role of the courts in navigating these contentious issues. Download this episode to learn about a case that could shape the future of public health regulations in the Commonwealth and beyond.

In this episode of Legal Judg(e)ments, host Bob Stetson talks to Jeremy Cohen, a pioneer in pet litigation, about the unique pet case of *Lyman v. Lancer. When Brett Lyman and Sasha Lancer’s relationship ended, a custody battle erupted—not over children, but their beloved Pomeranian, Teddy Bear. This episode explores how courts treat pets as property and family members, the implications of this case for pet owners nationwide, and what it means for future legal disputes over our furry companions.

 What is the law? How does it work? What role do lawyers, litigants, and judges play in the law's development? In sum, what moves the law in American society? I'm Bob Stetson, a Boston-based trial lawyer and the host of the podcast Legal Judg(e)ments. After 17 years in private legal practice, I still don't have a perfect answer to these important societal questions. 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.

In the famous American comic strip, The Wizard of Id, the Golden Rule means “Whoever has the gold makes the rules!” And so it’s been in the construction industry time immemorial. In this episode, Bob and Brad Croft discuss Tocci Building Corp. v. IRIV Partners and how the Golden Rule shaped recent statutory enactments in the construction industry and judicial interpretations of them.

Guest Paul Edelstein joins Bob Stetson to explore the critical issue of self-help evictions and the fight for housing justice. This episode centers on the Solis family from Brooklyn, New York, who faced a harrowing eviction attempt by their landlord, employing tactics like utility shutoffs, demolition work, and false legal notices. Their subsequent ten-year legal journey highlights the stark realities of informal evictions and their impact on society's most vulnerable. Through the case of Solis vs. Aguilar, Bob and Paul examine the balance between tenants' rights and landlords' actions, emphasizing the importance of due process as a cornerstone of liberty and dignity.

Listen to Bob Stetson and returning guest Ben Robbins from the New England Legal Foundation explore the separation of powers in the context of federal administrative agencies, the historical expansion of the administrative state, the Supreme Court's 1984 Chevron decision, and its implications for the separation of powers through the lens of a new rule by the National Marine Fisheries Council.

In this episode of Legal Judg(e)ments, Bob Stetson and his guest, John Elwood, discuss Counterman vs. Colorado, the Supreme Court’s recent decision balancing free speech rights against protection from abuse.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.

In this episode of Legal Judg(e)ments, Bob Stetson and his guest, Richard Gottlieb, dissect Coughlin v. Lac Du Flambeau Band of Lake Superior Chippewa Indians, a significant legal battle at the intersection of tribal sovereign immunity and bankruptcy law. They explore the historical concept of sovereign immunity and its application to Native American tribes, focusing on the Clear Statement Rule for waiving sovereign immunity. This episode offers an insightful look into a case that challenges the limits of tribal immunity and the protections provided by bankruptcy law.

In this thought-provoking episode, Bob Stetson and JoshuaThompson, Director of Equality and Opportunity Litigation at the Pacific LegalFoundation, discuss the landmark case of Cedar Point Nursery vs. Hassid andexplore the intricate balance between private property rights and publicinterests. What constitutes a 'taking' and how far government regulations cango in the name of the public good? 

Bob talks with the Institute for Justice’s Mike Greenberg about a Michigan town’s use of drones to enforce a land use regulation in Long Lake Township v. Maxon.

In the first episode of season 3, O’Melveny & Myers LLP’s John Kappos explains to Bob how his representation of two Massachusetts doctors led to a decision on whether medical-aid-in-dying qualifies as a fundamental constitutional right in Kligler v. Attorney General.

Season 3 of Legal Judg(e)ments officially launches on Monday, October 16.

In Season 2’s final episode, Bob and Joe Simons discuss Hines v. Cummings Properties; a closely watched commercial real estate case in which an appellate court invalidated a commonly used lease acceleration clause as an unenforceable penalty.

Bob and nationally renowned appellate attorney, MC Sungaila discuss In re Grand Jury – the closely-watched attorney-client privilege case that made its way up to the Supreme Court – and how the scope of the attorney-client privilege can have significant, real-world impacts on the practice of lawyering for businesses and corporations.  

Bob and Sammy Nabulsi discuss the sprawling legal battle over the reconstruction of a bridge in Boston Harbor at the center of City of Boston v. Conservation Commission of Quincy.

Bob and class action defense lawyer Mark Aronsson discuss Cabrera v. Auto Max Preowned, Inc. and how a judge's interpretation of a procedural rule can lead to bet-the-company litigation.

Bob and Frank Saccoccio discuss how the Supreme Court’s originalist interpretation of the Second Amendment led a court to invalidate Rhode Island’s stun gun ban in O’Neil v. Nerohna.

Bob and Greg Pagnini discuss how monks brewing beer led to federal litigation involving the Religious Land Use and Institutionalized Persons Act in Shrine of St. Nicholas v. Marblehead.

Bob and New England Legal Foundation's Ben Robbins discuss Tracer Lane II Realty, LLC v. City of Waltham and how the unintended consequences of a 1946 zoning bylaw could include the development of large-scale solar systems in residential neighborhoods.

Bob talks with legal titan Wayne Dennison to discuss his high-profile representation of international movie star Johnny Depp in what's been dubbed the first "trial by Tik Tok": Depp v. Heard.

Bob and Robert Galvin discuss Tenczar v. Indian Pond Country Club, Inc. and what happens when a home ostensibly becomes a part of a golf course.

Bob and Liberty Counsel’s Roger Gannam talk about Shurtleff v. City of Boston; the United States Supreme Court’s landmark First Amendment case involving the City’s flag-raising program.

We’re back with another season of Legal Judg(e)ments! Catch-up on Season 1 now and subscribe wherever you get your podcasts. The new season begins on October 17th.

In the final episode of Season 1, Bob talks with Scott Sinrich about his pro bono work in Stearns v. Montiero and how, despite popular belief, lawyering remains a noble profession.

In discussing Cunningham v. Lyft, Bob and New England Legal Foundation’s Ben Robbins address recent judicial interpretations of the Federal Arbitration Act, how they impact the business and legal world and whether countermeasures employed by the plaintiffs’ bar will make big business think twice about arbitration in the future.

In discussing Avila v. Boston Public Health Commission, Bob and Jordana Greenman talk about whether Boston’s eviction moratorium violates “due process of law” and how campaign rhetoric may have led to the implementation of this law. 

Bob and Dan Dain talk about the role of the judiciary in land use litigation and how the concept of “injury”, as interpreted by the court in Murchison v. Zoning Board of Appeals of Sherborn, saved real estate development in Massachusetts, particularly in “down zoning” jurisdictions like Boston. Dan also explains how zoning regulations constitute the single greatest contributor to the obesity crisis in America. A must listen for all land use lawyers, town planners, and real estate developers.

In part II of Sullivan v. Gagliardi, Peter McGlynn and Bob Stetson discuss how the oldest continuous court in the Western Hemisphere rejected the moral principles of St. Thomas Aquinas in the home sale context and what the legislature can do to rectify the decision.

The first in a two-part episode about Sullivan v. Gagliardi.  Peter McGlynn talks to Bob about what happens when your client’s home turns into a nightmare.  This is a must-listen for all home owners and real estate attorneys.

Attorney Joe Downes tells Bob about his legal strategies in Bass River Tennis Corp. v. Barros; a battle for control over a popular tennis club that led to five different lawsuits and eleven separate appeals.

Bob sits down with Jennifer LaManna to talk about her forceful and successful defense of the First Amendment in Shak v. Shak. This episode is a must-listen for all divorce practitioners.

Bob "Zooms” with Andy Caplan about his case Curtatone v. Barstool Sports, Inc. including how the historical fight against organized crime and modern “virtue signaling” set the stage for a fight between a well-known and popular media personality and the mayor of a city just outside of Boston.

Bob talks with the author of a popular legal treatise, Jordan Shapiro,  about his case Haddad v. Haddad and how the trusts and estates bar can virtually eliminate will contests by using modern technology. As a bonus, Jordan also discusses an important homestead law development. 

Bob is joined by Andrea Martin to discuss her groundbreaking case of UMNV 205 – 207 Newbury LLC v. Caffe Nero Americas, Inc. They also discuss how swimming led to this momentous application of the doctrine of frustration of purpose in the middle of a pandemic.

Oliver Wendell Holmes, Jr. said, “The life of the law has not been logic; it has been experience.” But, that famous statement misses a key ingredient in the law: the lawyers. Legal judgments often depend on the judgements of lawyers just as much as logic or societal experience. Boston trial lawyer Bob Stetson examines the litigation strategies and arguments that move the law through the prism of important civil cases.