David Holmes is a business lawyer.

He counsels and advocates for business owners and their businesses across a broad range of matters including initial organization, governing documents, operations and contracting, acquisition, disposition, finance, planning/strategy, disputes and litigation matters. David also advises clients on planning and strategy and advocates for them in commercial litigation matters.

Business Organizations. He represents business owners in the formation of business organizations for investment and operating purposes. He regularly counsels clients on and prepares buy-sell, employment and compensation documents.

Mergers and Acquisitions. He represents buyers, sellers, and investors in asset purchases, equity purchases, venture capital and investment transactions.

Investment and Finance. He represents borrowers, lenders, and investors in business finance transactions including debt and equity-based finance, mezzanine lending acquisition and construction finance and syndicated loan transactions.

Real Estate. He represents buyers, sellers, lenders and borrowers in commercial and residential real estate transactions and related matters.

Asset Protection. He assists clients in identifying assets that are exposed to the risks of litigation and implements protection strategies that are consistent with existing financial and estate plans, including family limited partnerships and asset protection trusts.

General Counsel. David serves as outside general counsel to a number of business clients whom he regularly advises on legal matters including strategy; contract negotiation, drafting, and disputes; employment and compensation matters; finance and leasing transactions; facility leasing; loan transactions and workouts; shareholder and equity buy sell transactions; spinoffs and reorganizations; mergers, acquisitions and dispositions. David has had the privilege of representing a number of significant businesses from the organization through growth, acquisitions, and ultimate sale by the original founders.

David’s experience extends to a number of sectors including hospitality, manufacturing, agriculture, construction, professional services, and health care. In the agricultural sector, he has served as counsel to large, multi-use landowners in a variety of operating and transactional matters. In the construction industry, he represents owners, general contractors, and subcontractors in project documents, payment administration, and design, defect, and related litigation. In the healthcare sector he represents individual physicians, group medical practices, and healthcare facilities in employment and related agreements, practice documents, multi-party arrangements, transactions, and healthcare compliance. In hospitality, he has served as project counsel to a significant resort project including acquisition, finance, construction and development, contracting, and permitting.

Representative Experience

  • Project general counsel to high nine-figure resort development, representing developer in all aspects of project including acquisitions, government relations, construction, contracting, finance and compliance
  • Lead counsel to seller/target in high eight-figure public-private acquisition
  • Represented borrower in $175m construction and development loan transaction
  • Represented borrower in $30m commercial revolving line of credit loan transaction
  • Outside counsel to large multi-specialty group medical practice providing representation in all aspects of operations including acquisitions, employment, finance, and compliance
  • Represented buyers and sellers in multiple golf course, golf club acquisition transactions
  • Counsel to borrower in convertible mezzanine debt transaction
  • Counsel to company in preferred stock investment transaction with venture capital investor
  • Successfully settled claims on behalf of more than 20 condominium purchasers under Interstate Land Sales Full Disclosure Act
  • Successfully represented condominium developer in defense of seven figure construction defect claims
  • Successfully defended private golf and country club in defense of litigation initiated by group of former members regarding membership redemption rights
  • Achieved favorable settlement on behalf of commercial property owner against insurance agency for failure to procure property insurance
  • Successful defense of residential developer in state and federal fraud claims
  • Represented regional auto dealer in favorable settlement of significant construction litigation matter
  • Co-counsel to seller, with team of attorneys, in largest public acquisition of private lands in Florida history
  • Obtained favorable settlement on behalf of borrower in lender liability claim involving breach of implied covenant of good faith and fair dealing
  • Represented corporate client in developing outside director equity compensation plan
  • Represented large condominium association in complex litigation involving developer finance default and receivership
  • Represented hospitality industry client in private equity finance transaction
  • Represented multiple clients in claims arising out of BP oil spill disaster in Gulf of Mexico
  • Represented nutraceutical industry leader in mezzanine finance transaction
  • Represented multiple commercial clients in litigation and transactions resulting in debt restructuring, resolution, and/or modification
  • General Counsel, Telegraph Cypress Water Control District
  • Associate General Counsel, Charlotte County Sheriff’s Office


  • J.D., cum laude, Stetson University College of Law, 1993
  • B.A., University of Florida, Political Science and History, 1990

Bar Admissions


Honors & Accolades

  •  AV Preeminent® Peer Review Rating, Martindale-Hubbell
  • Listed in The Best Lawyers in America for Construction Litigation, 2019-2021
  • Named to the list of Super Lawyers in Florida Super Lawyers Magazine, 2011, 2014-2021
  • Named to the list of Florida’s Legal Elite in Florida Trend Magazine, 2015
  • Leadership Florida Class XXXII, 2013-2014


  • Member, The Florida Bar
  • Admitted to practice: U.S. Supreme Court, U.S. Court of Appeals, 11th Circuit, U.S. District Court for the Middle District of Florida , U.S. Tax Court, and All Florida State Courts
  • Member, Charlotte County Bar Association
  • Certified Circuit Court Mediator, State of Florida
  • Chair, Twentieth Judicial Circuit Grievance Committee “C”, State of Florida, 2007-2008

Community Involvement

  • Board of Trustees, Florida Gulf Coast Foundation
  • Member, Board of Trustees, Charlotte Regional Medical Center
  • Organizer and Director, Calusa National Bank
  • Member, Paralegal Advisory Committee, School of Business and Technology at Florida SouthWestern State College
  • President, Charlotte County Chamber of Commerce, 2002-2003
  • Member, Florida Gulf Coast University Charlotte Center Advisory Board