Meet Cliff Shepard
“Decades of experience as an advocate, counselor, and neutral — helping parties navigate complex disputes with preparation, judgment, and a practical focus on resolution.”
“Decades of experience as an advocate, counselor, and neutral — helping parties navigate complex disputes with preparation, judgment, and a practical focus on resolution.”
Cliff Shepard is President and Managing Shareholder of Shepard, Smith, Hand & Brackins, P.A., and a Florida Supreme Court Certified Circuit Court and Appellate Mediator and Certified Arbitrator. He brings more than four decades of legal experience to the mediation, arbitration, and dispute-resolution process.
Cliff’s career has included complex civil litigation, municipal governance, land use, real estate, redevelopment, construction, insurance-related matters, and community association law. That breadth of experience allows him to understand not only the legal issues in dispute, but also the practical, financial, regulatory, and personal considerations that often determine whether a matter can be resolved. His approach is practical, prepared, and focused on helping parties move from entrenched positions toward durable solutions.
Cliff earned his Bachelor of Science in Journalism from the University of Florida in 1981, a background that helped shape the communication, writing, and analytical skills that have remained central to his legal career. He earned his Juris Doctor from the University of Florida Levin College of Law in 1985, where he was a member of the Trial Competition Team, served as Managing Editor of The Verdict, and was active in student government.
Those early experiences in advocacy, communication, and leadership helped form the foundation for a career devoted to problem-solving, careful analysis, and effective representation in complex matters.
Over the course of his career, Cliff has developed a broad and substantive legal practice. He is Board Certified by The Florida Bar in City, County and Local Government Law and has served as City Attorney for Maitland, Apopka, Ponce Inlet, and Eatonville. He has also provided land use counsel to the cities of New Smyrna Beach and Satellite Beach, among others, and serves as General Counsel to the Florida Redevelopment Association.
Cliff is admitted to practice in Florida, the District of Columbia, and Tennessee, as well as before the United States Supreme Court, all Florida federal district courts, and the United States Tax Court. He is also an approved agent for Attorneys’ Title Fund.
This background gives Cliff a working understanding of the legal, governmental, regulatory, and business realities that often shape disputes long before they reach mediation or arbitration. When serving as a neutral, he brings that perspective to the process without losing sight of the parties’ need for fairness, efficiency, and practical resolution.
Cliff’s dispute-resolution practice is grounded in the belief that many matters can be resolved more effectively outside the courtroom when the parties have a prepared, engaged, and experienced neutral. As a Florida Supreme Court Certified Circuit Court and Appellate Mediator and Certified Arbitrator, he is available to assist parties at both the trial and appellate stages of litigation, as well as before litigation becomes unavoidable.
His approach draws on decades of experience as a litigator, counselor, and government attorney. He works to understand the issues, identify practical obstacles to resolution, and help parties evaluate risk, cost, timing, and the broader consequences of continued litigation. Attorneys and clients value his preparation, patience, legal judgment, and ability to keep negotiations focused and productive.
Cliff’s work has been recognized consistently by his peers and by the legal profession. He has held an AV Preeminent rating from Martindale-Hubbell — its highest peer-review rating for professional excellence and ethical standards — continuously since 1995.
He has been listed in The Best Lawyers in America each year since 2018 and has been selected as a Florida Super Lawyer for approximately twenty consecutive years, from 2006 through 2026. He has also been recognized by Florida Trend as a Legal Elite in Governmental and Administrative Law and Commercial Litigation, and he holds a 10.0 rating on Avvo.
In addition to his law practice and dispute-resolution work, Cliff has devoted substantial time to professional service and legal education. He is a Past President of the Mid-Florida Chapter of the Community Associations Institute and has served as Past Chair of the editorial board of The Florida Bar Journal and News.
He is a frequent continuing legal education speaker on land use, the Sunshine Law, public records, ethics, community redevelopment agencies, construction law, real estate, and community association law. That commitment to education reflects the same principle that guides his work as a neutral: better outcomes are more likely when parties are informed, prepared, and treated with respect.
Cliff’s role as a neutral is to help parties make informed decisions, assess risk realistically, and explore solutions that may not be available through continued litigation. His goal is not simply to move cases off a docket, but to help parties reach resolutions that are legally sound, practical, and durable.
When you need a mediator who combines real-world legal experience with a genuine commitment to resolution, Cliff Shepard is ready to help. Contact us today to discuss your matter and schedule a mediation session.
