Seeking and retaining great talent has always been a major goal of our organization. Our family of attorneys is the best Florida has to offer.

Seeking and retaining great talent has always been a major goal of our organization. Our family of attorneys is the best Florida has to offer.

J.E. Cheek, III


329 Park Avenue North
Second Floor
PO Box 880
Winter Park, Florida
Fx. 407-645-3728

Direct Phone: 407-246-8670

Best Lawyers 2020


Trippe Cheek has been helping individuals, businesses, companies, estates, trusts, and governmental entities, with legal advice and in courtrooms and boardrooms, for over thirty 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 Development and Growth 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.

  • Vanderbilt University School of Law (1987)
  • The University of the South (magna cum laude, 1984)
Professional Certifications and Memberships
  • The Florida Bar
  • Tennessee Bar Association
  • Orange County Bar Association

Trippe has been honored by the Orange County Bar Association for free legal services provided to lower income citizens, has received the “Harris Rosen Award” from Tee-Lo Golf, a charity serving underprivileged school-age children, and has been a board member of the St. Michael’s Nursery School and president of the College Park Little League. He serves on the Real Estate Committee of the Episcopal Diocese of Central Florida.

Professional Recognitions and Awards
  • Rated “AV Preeminent” by Martindale Hubbell
  • The Best Lawyers in America©
  • Super Lawyers
Bar Admissions
  • Florida (1988)
  • Tennessee (1987)
  • United States Supreme Court
  • United States Eleventh Circuit Court of Appeals
  • United States District Court, Middle District of Florida
  • United States District Court, Eastern District of Tennessee