About Robert H.
Robert H. Friedman studied labor relations and the law. He earned a B.S. in Industrial and Labor Relations from Cornell University in 1991 and a J.D. from Harvard Law School in 1995. Those years set the stage for a career spent largely in insurance coverage work.
He began practicing as a litigation attorney in the late 1990s. In 1999 he joined Dickstein Shapiro LLP as an insurance coverage litigator, handling coverage disputes and related matters. The role placed him on teams that confronted policy interpretation and allocation issues during litigation.
By 2006 he had taken on a leadership role. He became head of the Insurance Coverage Practice at Gunster Yoakley & Stewart P.A. The post involved overseeing coverage strategies and coordinating litigation efforts for insurers and policyholders. It also meant supervising other lawyers and managing complex docket schedules.
Friedman’s background combines a foundation in labor relations with traditional legal training. That mix helps when insurance disputes intersect with employment, workplace injury, or labor issues. He has spent more than two decades focused on the contours of insurance policies, exclusions, and the litigation that flows from contested claims.
His work has included counseling clients on coverage positions, preparing coverage opinions, and litigating coverage defenses. He has operated on both sides of coverage questions, addressing insurer and insured perspectives. Colleagues describe him as precise in contract reading and methodical in litigation planning.
Outside of court papers and depositions, Friedman allocates time to mentoring junior attorneys and refining practice group procedures. The management experience he gained while leading a practice group informs how he approaches case staffing and client communication. He emphasizes clear legal analysis and practical options for resolving coverage disputes.
In his day-to-day practice he blends litigation experience with coverage counseling. He continues to handle disputes over policy language, exclusions, and indemnity obligations. As of 2026, he concentrates his practice on insurance coverage matters, including litigation and counseling.
