Boston, MA - Imagine owning your business, municipality, or agency property for decades. Then one day, a certified letter arrives from the city. Inside, it explains that a new highway, school, or commercial development is planned—and your property sits directly in the path of progress. The government will be taking it, whether you agree or not. That is eminent domain.

For most people it’s shocking and unsettling. Questions flood in: Do you have rights? Are you being treated fairly? The power of the government to take private property for public use—so long as it provides “just compensation”—can feel profoundly unbalanced. In those moments, clarity and experienced legal guidance matter. That’s where Attorney John S. Leonard comes in.

For more than four decades, John S. Leonard has dedicated his legal career to navigating the complex, high-stakes world of eminent domain and real property damage. As a seasoned trial lawyer, he has represented private individuals, businesses, municipalities, and public agencies in matters involving eminent domain, regulatory takings, inverse condemnation, relocation assistance, and real estate tax abatement.

Over the course of his career, Mr. Leonard has tried more than seventy-five cases to successful jury verdicts, many resulting in multi-million-dollar awards. His reputation for excellence is rooted not only in results, but in his deep command of the law and his ability to guide clients through emotionally charged situations with confidence and care.

In recognition of his leadership in the field, Mr. Leonard was named Massachusetts Lawyer of the Year in Eminent Domain in 2017 by Best Lawyers, the oldest and most respected peer-reviewed legal publication in the profession.

Born in South Boston, Mr. Leonard’s path into eminent domain law began early in his career while practicing at a prominent Boston general practice firm. There, he was mentored by a senior partner specializing in eminent domain—an experience that would shape his professional trajectory. After six to eight years of intensive training, he developed his own eminent domain practice within the firm, eventually spending 25 years there before launching his own office. Mr. Leonard wholeheartedly credits much of his success to the unwavering support of his family. He and his wife Denise—who retired after four decades as a fourth-grade teacher in Quincy—have been married for 52 years.

For more than 20 years, he has served as senior partner at the Law Offices of John S. Leonard, LLC, where he focuses almost exclusively on civil eminent domain cases. His standing in the legal community is reflected in his AV Preeminent® rating from Martindale–Hubbell, a distinction he has held continuously since 1985.

In addition to his extensive trial experience, Mr. Leonard has argued numerous appeals before the Massachusetts Appeals Court, the Supreme Judicial Court of Massachusetts, and the United States Court of Appeals for the First Circuit. He is also a widely respected author and lecturer on eminent domain law, frequently educating other attorneys on trial preparation and litigation strategy.

His practice extends beyond property law to include complex commercial litigation involving contracts, labor and employment disputes, construction claims, real estate conflicts, and domestic relations—bringing a broad legal perspective to every case he handles.

Mr. Leonard’s commitment to fairness extends beyond private practice. For 25 years, he served as Chairman of the Milton Board of Appeals, hearing hundreds of zoning cases and participating in related litigation. During his tenure, the town of Milton underwent significant transformation as highway and transit expansions reshaped the community. His leadership helped balance municipal growth with respect for residents’ rights.

Their son John is an accomplished media professional, a Boston University graduate who has worked with major broadcast networks, produced Olympic coverage from Greece, and earned an Emmy Award. Their daughter Laurie graduated with honors from Milton Academy, Dartmouth College, and Cornell Law School. After practicing labor and employment law in New York, she joined her father’s firm, where she now handles labor and employment matters while raising her son, Thomas.

Today, Mr. Leonard continues to expand his practice with a clear mission: to ensure that property owners whose land is taken through eminent domain receive fair, just compensation—and that municipalities conduct takings with transparency, respect, and accuracy to avoid unnecessary litigation.

Whether representing individuals facing the loss of a home or advising public agencies on responsible valuation practices, Mr. Leonard brings balance, integrity, and unmatched experience to every case.

His career reflects more than legal success. It tells the story of a lawyer who understands that behind every parcel of land is a life, a livelihood, and a legacy worth protecting.

For more information about our guest, please visit https://www.jsleonardlaw.com/