John M. "Jay" Brennan Attorney At Law

Diligent, steadfast advocate providing business litigation solutions for corporations and individuals across Florida. Helping clients resolve disputes in the business, health care, banking, and real estate sectors.

Jay Brennan is a seasoned, thoughtful litigator with deep roots in Central Florida. He has watched the city of Orlando grow and thrive throughout his practice, evolving his approach over the last four decades to meet and exceed changing client needs and expectations. Jay represents financial institutions, individuals, corporations, and other business entities in complex civil and commercial litigation matters at both the trial and appellate levels.

A steady partner for businesses navigating the cyclical nature of Florida’s dynamic economy, Jay provides calm, measured guidance in a wide array of corporate and transactional disputes across numerous sectors, including banking, health care, retail, and real estate. He collaborates with financial institutions, hospitals, insurance companies, and large employers. Notable client relationships include AdventHealth, Parrish Medical Center, TD Bank, and Walmart.

Jay is dedicated to creating positive outcomes for his clients, delivering efficient and effective solutions with each and every matter. His expertise includes contract disputes, corporate and partnership disputes, antitrust, mortgage foreclosure, commercial collections, commercial landlord/tenant litigation, business tort and trade secret litigation, employment contract and non-competition disputes, commercial products liability, franchise and manufacturer/dealer disputes, and construction disputes. Jay takes great pride in his tenure at the firm and is committed to teaming with GrayRobinson colleagues in the corporate, labor and employment, health care, and other practices to support his clients with well-rounded, robust counsel. 

• Notable Work
  • Morgan v. AdventHealth Orlando, MSI and NACS, Case No. 6:18-cv-1342-Orl-78DCI, United States District Court, Middle District of Florida, Orlando Division - Defeated motion for class certification in Fair Debt Collection Practices Act Claim and then secured dismissal with prejudice of $90 million class action claim against AdventHealth Orlando
  • Parrish Medical Center v. McKesson Technologies, Inc., Case No. 6:16-cv-00637-PGB-DAB, United States District Court, Middle District of Florida, Orlando Division - Recovered $4.25 million for Parrish Medical Center for failed IT implementation for entire hospital and secured dismissal of McKesson’s multi-million counterclaim against Parrish Medical Center with prejudice
  • Sprys v. Wal-Mart Stores, Inc., Case No. 98-1188-CIV-ORL-31DAB, U.S. District Court, Middle District of Florida, Orlando Division - Successful defense of Wal-Mart in $100 million False Claims Act claim of pharmacy price discrimination and alleged Medicaid fraud
  • Harborside 17 Partners, LLC; US Euro Equity, Ltd.; JUSA Holdings Harborside, Ltd.; Harborside Holdings, NC, Ltd.; Wolfgang Dueren and Jupiter USA, Inc. v. Warren Stanchina; Alan M. Whitney, Mary Lynn Stanchina, Harborside Joint Venture; GreatLand, LLC; US Euro Partners, LLC; and Robert L. Sirianni, Case No. 2007-CA-612, Circuit Court, Orange County, Florida - Successful defense of $7 million real estate fraud claim and recovery of $7 million settlement in favor of our clients
  • Cockman v. Spearman, Case No.: 2014-CA-01130-O, Circuit Court, Orange County, Florida - Recovered Final Judgment for $1,917,181.25 and foiled Ponzi Scheme resulting in arrest and conviction of perpetrator – case featured on Crime Watch Daily
• Recognition
  • Best Lawyers in America, 2006-2024
  • Banking and Finance Law
  • Bet-the-Company Litigation
  • Commercial Litigation
  • Florida Super Lawyers, selected for inclusion, 2006-2023
  • Orlando Magazine, Best Lawyers, 2007-2021
  • Banking and Finance Law
  • Commercial Litigation
  • Bet-the-Company Litigation
• Insights
  • "Doing Deals and Disputes in 2020: Revive, Restructure, or Rend Apart," Association of Corporate Counsel (ACC) of Central Florida, October 15, 2020
• Affiliations
  •  American Bar Association
    • Litigation and Antitrust Sections
  • Academy of Florida Trial Lawyers
  • American Trial Lawyers Association
  • The Florida Bar
    • Trial Lawyers Section
  • Million Dollar Advocates Forum
  • Orange County Bar Association
  • Appointed to Merit Selection Panel to choose United States Magistrate Judge for the Middle District of Florida
  • Annika Sorenstam Foundation, Chair
  • The First Tee of Central Florida, Former Director
  • Ken Griffey Jr. Family Foundation, Chair
  • Orlando Science Center, Former Board Member
  • Rollins College Alumni Association
• Credentials
  • J.D., University of Miami, J.D., 1979, with Honors
  • B.A., Rollins College, B.A., 1976 
• Admissions
  • Florida
  • U.S. Court of Appeals for the 11th Circuit
  • U.S. District Court for the Middle and Northern Districts of Florida
  • U.S. Supreme Court