Jonathan Kent Osborne

Trial Court Experience

• First-chair trial counsel in a jury trial in Miami-Dade County Circuit Court, obtained a defense verdict.
• Prevailed on summary judgment in a statutory and breach of contract action in state court resulting in an award of prevailing party attorneys’ fees and costs for the client.
• Served as first chair counsel in a business dispute against a publicly traded national bank.
• Served as first chair counsel in arbitration successfully litigated through decision on behalf of a Florida higher education institution.
• Secured dismissal with prejudice of a complaint alleging invasion of privacy and constructive fraud in the 2nd Judicial Circuit of Florida.
• Defended a publicly traded company in shareholder derivative litigation brought in federal and state court.
• Defended an AMLAW 50 Firm in a lawsuit brought by a federal receiver alleging negligence in the U.S. District Court for the Southern District of Florida.
• Defended a class action lawsuit against a subsidiary of a publicly traded energy company.
• Represented a joint venture partner in an arbitration before the American Arbitration Association.
• Argued successful appeals in the U.S. Court of Appeals for the 11th and D.C. Circuits, and Florida’s Third District Court of Appeal.

White Collar Defense, Investigations and Compliance Experience

• Defended certified public accountant and firm in connection with a Department of Justice Investigation (no charges threatened).
• Defended petitioner and his estate against a cryptocurrency seizure by the Florida Office of Attorney General, Florida Department of Law Enforcement, and related criminal investigation by the Office of Statewide Prosecution (obtained return of funds and dismissal).
• Defended entrepreneurs and related companies in a criminal investigation and related civil proceedings in the Western District of Pennsylvania (no charges threatened).
• Defended medical company in Food and Drug Administration and US Attorney’s Office investigation (no charges brought).
• Defended employees in a criminal investigation and related civil matter by the Justice Department alleging violations of the False Claims Act (no penalties).
• Served as co-counsel for a public official in a criminal case charged by the Miami-Dade State Attorney’s Office (charges dismissed).
• Defended public official in Florida Commission on Ethics investigation (no penalty imposed).
• Defended public official in Florida Statewide Grand Jury investigation (no charges threatened).
• Defended public official in Grand Jury investigation in north Florida (no charges threatened).
• Defended subjects of a Securities & Exchange Commission investigation concerning alleged insider trading (no charges filed).
• Defended a physician in an investigation by Broward Sheriff’s Office and in response to related civil demand letter (finding of no probable cause).
• Defended a physician in an investigation by the Florida Attorney General (no charges brought)
• Defended importer and target of federal investigation in response to allegations of illegal smuggling of goods and customs violations (no charges brought).
• Defended target of federal fraud investigation in response to grand jury subpoena (no charges brought).
• Defended client against criminal forfeiture of assets (obtained partial release of assets).
• Defended target of federal investigation concerning alleged embezzlement (no charges threatened).
• Defended company in connection with criminal arson investigation (no charges brought).
• Assisted client in connection with application to the Office of Foreign Assets Control (OFAC) concerning business in a sanctioned country.
• Led internal investigation concerning embezzlement and cross-border fraud by a high-ranking company official.
• Led internal investigation concerning potential impact to endangered species.
• Led internal investigation concerning alleged violations of environmental protection regulations.
• Led internal investigation concerning alleged violations of federal securities laws.
• Co-led internal investigation concerning alleged racial, ethnic and religious discrimination against a hospitality company.
• Led internal investigation on behalf of company concerning alleged sexual misconduct by a board member.
• Led internal investigation on behalf of a Florida bank regarding allegations of bank and wire fraud.
• Advised company regarding compliance with federal criminal law in connection with internal investigation concerning alleged human trafficking.
• Represented an education organization in responding to an attempted cyber smear against a board member, and conducted a related investigation.

As a Federal Prosecutor

• As a federal prosecutor, represented the government in hundreds of trial-level proceedings, such as bench trials, bond hearings, plea hearings, sentencing hearings, suppression hearings, supervised release revocation hearings, and grand jury presentations.
• Prosecuted matters alleging violations of the Foreign Narcotics Kingpin Designation Act, an economic sanctions program administered and enforced by the Office of Foreign Assets Control of the U.S. Department of Treasury.
• Led more than 150 successful federal criminal prosecutions as an Assistant U.S. Attorney in the Southern District of Florida.

• Legal 500, "U.S. Miami Elite - White Collar Crime", Tier 4, 2026

• The Best Lawyers in America®, “Ones to Watch,” Criminal Defense: White-Collar, 2023-26
• South Florida Business Journal, 40 Under 40 Honoree, 2024
• Florida Super Lawyers, "Rising Star," 2020-24
• Haitian Lawyers Association, Presidential Award for Outstanding Service in the Community, 2024

Thought Leadership: Competition in Business and Athletics 

As a former college athlete, Jonathan explores the intersection of competition, business, and leadership on his podcast, Always an Athlete. Check out Always an Athlete.

Publications & Presentations

• "Effective Advocacy in Federal Court featuring the Honorable Rodolfo A. Ruiz, U.S. District Judge,” co-panelist, The Blueprints Webinar Series, April 2026
• "How to Become an Indispensable Associate," panelist, The Blueprints Webinar Series, January 2026
• “The Dinosaur in the Room, A Refresher on Attorney-Client Privilege with Specific Guidance for the Jurassic World of E-Discovery,” presenter, ACC South Florida, 14th Annual CLE Conference, September 2024
• “‘What Happens in Privilege Stays in Privilege,’ a Refresher for Corporate Counsel on the Attorney Client and Work-Product Doctrines in Florida,” ACC South Florida, 3Q 2024 Newsletter, September 2024
• “Career Path After Prosecution: What’s Next?” panelist, NBPA Conference, August 10, 2024, Boston, MA
• “The Essence of Inclusion,” Keynote Speaker on the Importance of Complying with the Supreme Court’s Harvard Decision, Fair360 Top 50 Awards Dinner, May 13, 2024, New York, NY
• “Confidentiality & Privilege,” Presenter, Florida Bar Young Lawyers Division, “Practicing with Professionalism” CLE Course, 2023, 2024
• Gunster’s 2024 Health Care Forum featuring the Honorable Jason Weida, Secretary at the Agency for Health Care Administration (ACHA), moderator, February 29, 2024
• “Call of Duty: Understanding privilege in Day-to-Day Operations,” presenter, ACC South Florida, 13th Annual CLE Conference, September 29, 2023
• “Ascending to the Bench,” panelist, with U.S. District Judge Rodney Smith and U.S. Magistrate Judge Panyotta Augustin-Birch, T.J. Reddick Bar Association, September 28, 2023
• “Human Trafficking and the Lawyer’s Role in Protecting the Most Vulnerable Members of Our Community,” Introductory Speaker, 2023 Federal Bench & Bar Conference, U.S. District Court for the Southern District of Florida
• "Understanding Investigations by Florida’s Commission on Ethics," author, Daily Business Review, August 31, 2023
• "Learning from the Legends," Lunch and Learn Speaker, U.S. District Court for the Southern District of Florida Judicial Intern Academy, 2022, 2023, 2024
• "5 Steps for Responding to an AG Investigation," author, Daily Business Review, May 18, 2023
• “Is this the End for Non-Compete Clauses? The Evolving Debate Surrounding Employment-Based Non-Compete Clauses, How It May Impact Your Company, and What To Do Moving Forward,”co-author, ACC South Florida Focus Q1, 2023
• "It Takes a Village: The Promise of the Southern District of Florida's Judicial Intern Academy to Inspire Mentorship and Leadership Through Service," author, The Federal Lawyermagazine, November/December 2022
• "Shaken Not Stirred: Surviving in Today's Class Action Climate," presenter, ACC South Florida, 12th Annual CLE Conference, September 16, 2022
• "Cyber Risk Management and Internal Threats," presenter, South Florida Public Risk Management Association Luncheon, September 15, 2022
• "Your Next Seven Years," keynote speaker, Pine Crest School Boca Raton Investiture, August 26, 2022
• "What to do if illegal activity occurs in your organization," speaker, On top of PR video podcast, May 2, 2022
• “Foreign Corrupt Practices Act,” Gunster CLE, April 13, 2022
• “Don’t Panic: Navigating the Evolving Cybersecurity Galaxy,” panelist, Globalaw Americas Regional Meeting – Miami, Florida, March 29, 2022
• “After Ukraine, Russian cyberattacks could come to US: How to defend yourself,” quoted, FoxNews.com, February 26, 2022
• "Momentum Is Building for Antitrust Reform. Here's What That Means for Big Tech," quoted, TIME, November 12, 2021
• "Developing Jury Appeals in Cases with Unsympathetic Witnesses or Clients," 2021 Federal Bar Association Annual Meeting & Convention, Moderator, September 23, 2021
• “Cybercrime: A Leading Threat to Business & National Security,” co-author, Association of Corporate Counsel 3Q 2021 Newsletter
• "Don't Lose your Way: Navigating the Cross-border Corporate Compliance Maze", Globalaw Webinar Series, September 15, 2021
• "The U.S. Supreme Court's Van Buren Decision Overrules 11th Circuit Precedent Concerning the Computer Fraud and Abuse Act", July 9, 2021
• "Corporate Internal Investigations", Gunster CLE, June 29, 2021
• "CEO Roundtable Luncheon,” African American Chamber of Commerce of Central Florida, June 11, 2021
• "C-Suite Fraud: The Roaring 2020s Threat to your Company", presenter, ACC South Florida CLE Conference, April 30, 2021
• "How to Level the Playing field of Cyberattacks", author, Hospitality Technology, January 26, 2021
• "Is this the beginning of the end for Google?" quoted, ITPro, December 6, 2020
• "Judicial Perspectives on Diversity & Inclusion in Federal Practice" with U.S. District Judges Singhal, Ruiz, and Smith, moderator, Federal Bar Association Webinar, Broward Chapter, December 4, 2020
• "Managing Ransomware Incidents in COVID Times," panelist, Gunster & Kaufman|Rossin Webinar, November 17, 2020
• "Post-Breach Response To Business Email Scams Is Critical," author, Law360, November 18, 2020
• "5 Key Ways to Avoid Cybercrime," co-author, HOTELS Magazine, November 17, 2020
• "Cyber-Safety in an Era of Hospitality Automation," co-author, Lodging Magazine, October 27, 2020
• "Criminal Justice & Race in South Florida – Historical & Contemporary Perspectives" from law enforcement, ADL Webinar, August 11, 2020
• "Have we become too reliant on Big Tech firms?" quoted, BBC.com, June 19, 2020
• "The Uptick in Litigation Due to COVID-19: How to Prepare Your Business," Gunster webinar, May 20, 2020
• "Re-Opening Florida: Guidance for Businesses to Protect Themselves, Employees & Customers," Greater Boca Raton Chamber of Commerce webinar, May 15, 2020
• "Re-Opening Florida: Guidance for Businesses to Protect Themselves, Employees & Customers," Gunster webinar, May 1, 2020
• "How to Protect Your Business from Potential Internal and External Cybersecurity Threats Amid the COVID-19 Pandemic," Gunster webinar, panelist, April 24, 2020
• "CARES Act: A Deep Dive for Legal Professionals," Gunster webinar, panelist, April 13, 2020
• "Antitrust Laws and Competitor Collaboration in the Face of COVID-19," author, Gunster Alerts & Publications, March 26, 2020
• "Businesses Beware: COVID-19 Fraud is Flourishing," author, Gunster Alerts & Publications, March 26, 2020
• "A Future in Criminal Law: the Challenges and Opportunities", panelist, Florida A&M School of Law, Orlando, Florida, 2018
• Trained AUSAs in the Southern District of Florida on “Best Practices” in Narcotics Cases, 2018
• “I Am a Star Foundation” program, keynote speaker, Jefferson Davis Middle School, Jacksonville, Florida, 2018
• Pine Crest School Investiture, keynote speaker, Boca Raton, Florida, 2014-16, 2018
• Multilateral Summit on Combating Crime in an Interconnected World, panelist, Kingston, Jamaica, 2017
• Trained new AUSAs in the Southern District of Florida in Narcotics Investigations, 2017
• S. firearms prosecutions for members of the Haitian National Police, Bureau of Alcohol, Tobacco, Firearms Training, speaker, Miami, Florida, 2017
• S. District Court for the Southern District of Florida’s “Law Day,” Diversity in the Law Panel on attorney career paths, panelist, Miami, Florida, 2017
• Intercultural Human Rights Law Review Symposium on Gun Control, panelist, St. Thomas University School of Law, Miami, Florida, 2017
• “Revisiting the Dream” of Dr. Martin Luther King Jr., panelist, Florida Atlantic University, 2015

Professional Associations & Memberships

• Federal Bar Association Broward County Chapter, President, 2025-Present

• St. Thomas University, College of Law, Board of Advisors, 2025-Present

• Federal Magistrate Merit Selection Panel Regarding Magistrate Judge Vacancies in the Southern District of Florida, 2022-Present

• Broward County Bar Association, Board Member, 2026

• Committee for the United States District Court for the Southern District of Florida 2023 Bench and Bar Conference, Member, 2022-23; 2024-25

• United States District Court for the Southern District of Florida Committee to Oversee Events Commemorating Jewish American Heritage Month, Member, 2024-25

• Leadership Florida, Connect Class 11

  • Connect Class 12 Selection Committee

• Harvard Law School Criminal Justice Institute, Trial Advocacy Workshop, Faculty, 2021-2024

• Emory University School of Law, Kessler-Eidson Program for Trial Techniques, Teaching Faculty, Spring 2024

• Adjunct Professor of Cyber Incident Response, Florida State University College of Law, Juris Master Program, 2022-23

• Broward County Sheriff's Office, Professional Standards Committee, 2021-25

• Florida Bar Committee on Cybersecurity and Private Law (Term 2028)

• Florida Bar Constitutional Judiciary Committee (Term 2024)

• Leadership Fort Lauderdale, Class 26

Civic & Community Service

• Children's Bereavement Center, Board Chair (2023-2025)

• U.S. Attorney's Office for the Southern District of Florida, Violence Reduction Partnership, volunteer, 2014-19

• Habitat for Humanity of Broward County, Youth Empowerment Program, 2013-17