Representative Matters

Edward Sylvester focuses his practice in the area of insurance coverage litigation. He is experienced with the analysis and litigation of a wide variety of commercial liability and professional liability policies, including commercial general liability, commercial auto, commercial property, architects and engineers, directors and officers, errors and omissions, RV and trucking, as well as commercial excess and commercial umbrella. Mr. Sylvester is also well-experienced with personal auto, personal life insurance and homeowners policies.

Mr. Sylvester has been involved in many significant cases interpreting an insurance company’s duties to defend and indemnify, including consideration of breaches to insuring agreements, policy conditions, policy exclusions, as well as interpretations of policy terms and definitions. He is well-versed with advising and litigating claims involving construction defects, copyright infringement, trademark and patent infringement, catastrophic personal injury, RV-trucking-auto accidents, property damage, as well as claims arising from professional activities of architects, engineers, directors, officers, brokers, and agents. Mr. Sylvester also handles coverage matters involving common law and statutory bad faith.

Professional Background

Mr. Sylvester joined Hinshaw & Culbertson LLP in November 2006. Previously, he worked extensively on insurance coverage matters with the Cleveland, Ohio law firm of Weston Hurd LLP. Mr. Sylvester is actively licensed in all Florida State and Federal Courts, as well as all Ohio State and Federal Courts.

In law school, Mr. Sylvester served two terms as the Research/Case and Comment Editor for the Akron Law Review and is a member of the Akron Law Alumni Association.

Prior to his legal career, Mr. Sylvester spent 10 years as Founder and President of Fistlaw, Inc., a martial arts school where he focused on self-defense instruction, video seminars and equipment design. He is a member of the Universal Society of Black Belts and holds a 5th Degree black belt.

Professional Affiliations

  • The Florida Bar
  • American Bar Association, Insurance Coverage Litigation Committee of the Section of Litigation

Representative Matters

Mr. Sylvester litigates first and third party insurance coverage matters in both state and federal forums. He has extensive experience with resolving disputes by summary judgment motion. Mr. Sylvester successfully litigated the following case in a federal jury trial:

  • Mid-Continent Cas. Co. v. American Pride Bldg. Co., LLC, et al., Case No. 2:07-CV-00258 (M.D. Fla. March 10, 2011) (jury rendered verdict in favor of Mid-Continent after finding the consent judgment entered into by American Pride was unreasonable in amount and tainted by bad faith, fraud, collusion or without any effort to minimize liability).

Mr. Sylvester is also is well-acquainted with appellate procedure and has achieved many successful results, including the following notable decision in the Supreme Court of Ohio:

  • Allen v. Johnson, 100 Ohio St.3d 276, 798 N.E.2d 591 (Ohio 2003) (reversing the appellate decision and reinstating judgment of trial court that Indiana Insurance Company had no coverage obligations because school districts are not authorized under Ohio statutes to purchase UM/UIM insurance for its off-duty employees or family members of such employees).


J.D., University of Akron School of Law, 2000

  • Research Case & Comment Editor, Akron Law Review

B.A., Baldwin – Wallace College, 1995, Business Administration