J.E. “Trippe” Cheek, III

Trippe Cheek has been helping individuals, businesses, companies, estates, trusts, and governmental entities, with legal advice and in courtrooms and boardrooms, for over thirty-seven years. He has a deep understanding of the world of litigation, including trials and appeals, and uses his legal and practical experience to serve as general counsel and an advisor to numerous clients.

Handling and Resolving Disputes

Trippe’s decades of trial and appellate experience include a consistent focus on the rights of his clients in all types of property, including real property, personal property, securities and investments, and financial accounts. He represents clients in a wide variety of matters, including:

• Complex civil and commercial disputes
• Fiduciary, probate, and trust disputes
• Real property valuation, including eminent domain and related disputes
• Property tax challenges
• Land use and property rights

General Counsel Advice

Trippe’s diversity of background and experience provide him the opportunity to work with clients who need general counsel advice on a wide scope of legal issues, from corporate governance, operations, and contractual matters, through the unique needs of non-profit institutions and foundations.  He has represented a large number of clients in this general counsel role, including:

• From small to very large businesses and corporations
• Cities, counties, and other local government entities
• Colleges and private schools
• Hospitality industry developers and owners
• Trusts and charitable foundations

Personal Background

Trippe has been a shareholder with Winderweedle, Haines, Ward & Woodman since 1993 and is now the Firm’s Chairman of the Board and General Counsel after serving for 15 years as the Firm’s President. He joined the Firm in the fall of 1988 after completing a federal judicial clerkship in the Eastern District of Tennessee. He is rated “AV” by Martindale-Hubbell and has been named to Best Lawyers and Super Lawyers lists, among others. Trippe is licensed to practice in Florida and Tennessee.

During his career, Trippe has been designated as lead counsel in legal matters for numerous individual, fiduciary, corporate, and governmental clients, including Osceola County, the Central Florida Expressway Authority, the City of Winter Park, Bank of America, Regions Bank, Tampa Bay Water Authority, St. Johns River Water Management District, Rollins College, Florida Southern College, and others. He is admitted to practice and has served as primary counsel on cases in state, federal, and bankruptcy courts as well as Florida District Courts of Appeal, the Florida Supreme Court, the Federal Eleventh Circuit Court of Appeals and the United States Supreme Court. Trippe spent twelve years as a board-certified appellate attorney in Florida. For five years, he served as the City Attorney for Winter Park, Florida. He is also general counsel to Rollins College.

Trippe is a member of the Board of Trustees of The University of the South, where he chairs the Growth and Development Committee.

Trippe is married to Tracy Lee Troutman, a native of Orlando, and they have two children. The family belongs to St. Michael’s Episcopal Church and supports various charitable and civic organizations.  He has coached a variety of youth sports, including managing a youth baseball team to the state tournament.