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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

J.E. Cheek, III

James Edward “Trippe” Cheek, III, a shareholder since 1993 and the Firm’s President/CEO, joined Winderweedle, Haines, Ward and Woodman in the fall of 1988 after completing a federal judicial clerkship in the Eastern District of Tennessee. Since that time, Trippe’s practice has been concentrated in the areas of complex civil matters, including land use and property rights; ad valorem tax law; real property law; administrative law; condemnation and contract; alternative dispute resolution; and trials and appeals. Trippe represents, among other clients, individuals, businesses, municipalities and other governmental agencies, and post-secondary educational institutions. He is rated “AV” by Martindale-Hubbell.

Recently, Trippe has spent much of his practice representing property owners developing projects in the Orange County tourism corridor and in areas such as Winter Park and Maitland, evaluating and analyzing property development regulations and issues, discussing projects with governmental staff, and making presentations to local government boards.

During his practice, Trippe has been designated as lead counsel in legal matters for numerous individual, corporate and governmental clients, including 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, Florida Supreme Court, 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 licensed to practice in Florida and Tennessee.

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 (1988)
  • 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.

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