Jonathan K. Osborne is a business litigation shareholder and co-chair of the firm’s White Collar Defense & Internal Investigations practice group. He began his practice at Gunster and later returned to the firm after serving in the U.S. Department of Justice as an Assistant United States Attorney in the Southern District of Florida.

Jonathan represents individuals and organizations in civil and white collar criminal matters and internal investigations. On the civil side, Jonathan has handled a variety of matters in federal and state court and arbitration. His clients include educational institutions, corporations, private equity firms, not-for-profits, health care organizations, and business and community leaders. On the regulatory and criminal sides, Jonathan has conducted internal investigations across industries. Drawing from his extensive grand jury and criminal investigations experience, he defends clients in responding to federal and state investigations and charges, including matters arising under the federal False Claims and Foreign Corrupt Practices Acts, the Treasury Department’s OFAC Sanctions Program, and the Florida Deceptive and Unfair Trade Practices Act. Jonathan also represents witnesses subpoenaed by government agencies.

While a federal prosecutor, Jonathan investigated and prosecuted a wide array of criminal violations. His cases involved allegations of fraud, computer crimes and identity theft, human smuggling, money laundering, corruption and bribery, narcotics and firearms trafficking, and violent crimes. Jonathan also partnered with the DEA and FDA to target the unlawful diversion of prescription medication, including opioids, by licensed medical professionals, as well as the purchase, importation and administration of counterfeit and unapproved prescription drugs.

In total, Jonathan led hundreds of criminal investigations, represented the United States in jury trials, and handled appeals before the United States Court of Appeals for the 11th Circuit. As part of the U.S. Attorney’s Office’s Violence Reduction Partnership, Jonathan founded a mentorship program at high schools in Miami. His commitment to mentorship continues through Gunster’s Leadership Training Academy which offers Florida law students leadership and legal training. Jonathan also serves on the teaching faculty in the Harvard Law School Criminal Justice Institute’s trial advocacy program and at the Florida State University College of Law.

Jonathan attended Georgetown University Law Center, where he briefed and argued an appeal against the government before the U.S. Court of Appeals for the District of Columbia Circuit. Jonathan played college basketball at the University of Nevada, Las Vegas and the University of Alaska-Fairbanks, where he won the athletic department’s community service award.

Trial Court Experience

  • Represents companies, educational institutions, and individuals in a variety of commercial disputes in state and federal courts, including class action and multi-district litigation matters
  • Defends health care organizations in federal qui tam litigation
  • Represents a publicly traded company in shareholder derivative litigation brought in federal and state court
  • Prevailed on summary judgment in a statutory and breach of contract action in state court
  • Served as first chair counsel in an arbitration successfully litigated through decision on behalf of a Florida higher education institution
  • Represented an AMLAW 50 Firm in a lawsuit brought by a federal receiver alleging negligence claim by receiver – U.S. District Court for the Southern District of Florida
  • Represented a joint venture partner in an arbitration before the American Arbitration Association
  • Represented a renewable energy company in an action to compel arbitration under the Federal Arbitration Act
  • Represented a precious metals seller in an alleged fraudulent metals scheme defense under the Commodities Exchange Act
  • Represented a Fortune 500 company in a breach of contract lawsuit
  • 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

White Collar Defense, Investigations, and Compliance Experience

  • Defends Florida businesses, physicians and medical practices, and individuals against federal and state criminal, civil and regulatory investigations
  • Assists clients in regulated industries, including banking, health care, and education with government compliance and subpoena response
  • Represents witnesses in federal and state criminal investigations and grand jury matters
  • Assists clients with compliance with the U.S. Treasury Department’s Office of Foreign Assets Control Sanctions Programs
  • Conducts anti-corruption and FCPA compliance training programs
  • Assists clients with cyber incident response
  • Defends clients against allegations of violating the Florida Deceptive and Unfair Practices Act (“FDUPTA”) brought by the office of the Florida Attorney General.
  • Represented a company and its founders against an FTC lawsuit and asset freeze in the Middle District of Florida.
  • Represented an elected official in response to an investigation opened by the Florida Commission on Ethics concerning complaints alleging improper conduct, resulting in dismissal of the complaints.
  • Represented a Florida-based community health care organization in False Claims Act litigation, resulting in dismissal of all claims against the client.
  • Represented a foreign bank in connection with analyzing applicability of U.S. Treasury Department financial sanctions under a Presidential Executive Order.
  • Represent clients from the health care, import-export, and money exchange industries in responding to criminal target letters from the U.S. Attorney’s Office for the Southern District of Florida.
  • Assisted Texas-based health care companies with responding to grand jury subpoenas concerning alleged fraud offenses conducted by a company employee.
  • Assisted a publicly traded health care company with responding to grand jury and trial subpoenas and with preparing its corporate representative for trial testimony.
  • Conducted an internal investigation of allegations of sexual harassment, hostile workplace environment, and financial improprieties against the CEO and Chairman of a not-for-profit corporation.
  • Conducted an internal investigation on behalf of a publicly traded company in the travel industry regarding allegations of securities fraud
  • Conducted an internal investigation on behalf of a Fortune 500 company regarding allegations of racial discrimination
  • Conducted an internal investigation on behalf of a Florida education nonprofit regarding allegations of executive misconduct
  • Represented an education organization in responding to an attempted cyber smear against a board member, and conducted a related investigation
  • Conducted an internal investigation on behalf of a Florida-based bank regarding allegations of bank and wire fraud
  • Conducted an internal investigation on behalf of a national healthcare organization regarding allegations of healthcare fraud
  • Conducted an internal compliance review on behalf of a health management organization.
  • Florida Super Lawyers, “Rising Star,” 2020-23
  • The Best Lawyers in America®, “Ones to Watch”
    • Criminal Defense: White-Collar, 2023-24
  • 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
  • 5 Steps for Responding to an AG Investigation,” author, Daily Business Review, May 18, 2023
  • “Is this the End for NonCompete Clauses? The Evolving Debate Surrounding Employment-Based NonCompete 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 Lawyer magazine, 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,” presenter, 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,, February 26, 2022
  • “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, speaker, September 15, 2021
  • “The U.S. Supreme Court’s Van Buren Decision Overrules 11th Circuit Precedent Concerning the Computer Fraud and Abuse Act”, author, July 9, 2021
  • “Corporate Internal Investigations”, presenter, Gunster CLE, June 29, 2021
  • “CEO Roundtable Luncheon”, moderator, 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: 11th Annual 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,” 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,” panelist, ADL Webinar, August 11, 2020
  • Have we become too reliant on Big Tech firms?” quoted,, 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
  • U.S. firearms prosecutions for members of the Haitian National Police, Bureau of Alcohol, Tobacco, Firearms Training, speaker, Miami, Florida, 2017
  • U.S. District Court for the Southern District of Florida’s “Law Day,” Diversity in the Law Panel, 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
  • Children’s Bereavement Center, Board Chair
  • Federal Bar Association Broward County Chapter, Treasurer
  • Florida Civic Advance, Board Member, 2023
  • Leadership Florida, Connect Class 11; Connect Class 12 Selection Committee
  • Federal Magistrate Merit Selection Panel Regarding Magistrate Judge Vacancy in Miami, Florida, Member, Summer 2023
  • Committee for the United States District Court for the Southern District of Florida 2023 Bench and Bar Conference, Member, 2022-23
  • Federal Magistrate Merit Selection Panel Regarding Magistrate Judge Vacancies in Fort Lauderdale and Miami, Florida, Member, Spring 2022
  • Harvard Law School Criminal Justice Institute, Trial Advocacy Workshop, Faculty, September 2021, 2022, 2023
  • 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, Civilian Member
  • Florida Bar Committee on Cybersecurity and Private Law (Term 2028)
  • Florida Bar Constitutional Judiciary Committee (Term 2024)
  • UNLV, Leadership & Social/Entrepreneurship Advisory Board, 2021-22
  • Leadership Fort Lauderdale, Class 26
  • 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

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