Jonathan K. Osborne is a business litigation shareholder and co-chair of the firm’s White Collar Criminal 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.

An experienced first chair trial attorney, Jonathan represents individuals and organizations in civil business litigation, including the defense of legal malpractice claims as well as white collar criminal matters and internal investigations. Jonathan has conducted internal investigations on behalf of companies across a variety of industry sectors, including hospitality, travel, education, healthcare, and banking. Drawing from his extensive grand jury and criminal investigations experience, he consults businesses and individuals in responding to government scrutiny and cyber security threats. Jonathan routinely advises companies, business leaders, nonprofit organizations, and healthcare professionals in connection with compliance with state and federal criminal law and other regulations, including the Foreign Corrupt Practices Act, the U.S. Department of the Treasury’s Office of Foreign Assets Control (OFAC) Sanctions Programs, the False Claims Act, and COVID-19 emergency orders.

During his time as a federal prosecutor, Jonathan investigated and prosecuted a wide array of criminal violations by companies and individuals. His cases involved allegations of fraud, computer crimes and identity theft, human smuggling, money laundering, narcotics and firearms trafficking, corruption, bribery and extortion, and murder. In several instances, Jonathan partnered with the Drug Enforcement Administration (DEA) and Food and Drug Administration (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 by physicians.

While a member of the International Narcotics and Money Laundering Section’s High Intensity Drug Trafficking Area (HIDTA) task force, Jonathan traveled throughout South America and the Caribbean and handled investigations focused on multinational cartels operating in Europe, South and Central America, and the Caribbean. Jonathan collaborated with investigators from federal, state and local law enforcement agencies and financial regulators, including the U.S. Department of the Treasury’s Office of Foreign Assets Control (OFAC).

During his time at the U.S. Attorney’s Office, Jonathan led hundreds of criminal investigations, represented the United States in jury trials, and argued matters 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 with the legal magnet programs at Law Enforcement Officers’ Memorial High School and Coral Reef Senior High School in Miami. His commitment to mentorship continues through his work on Gunster’s Diversity, Equity and Inclusion Committee, which established the Leadership Training Academy in 2021 to serve and inspire the next generation of Florida attorneys by providing law students with substantive leadership, legal training and mentorship opportunities.

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
  • 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 former shareholder in a securities fraud action against a corporation and directors
  • 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

White Collar Defense, Investigations, and Compliance Experience

  • Led more than 150 successful federal criminal prosecutions as an Assistant U.S. Attorney in the Southern District of Florida
  • Defends Florida businesses, physicians and medical practices, and individuals against federal and state criminal, civil and regulatory investigations
  • Represents clients in regulated industries, including banking, health care, and education with government compliance and subpoena response
  • 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 cyberattack preparation and response
  • 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

Appellate Experience

  • United States v. Joyner, 882 F.3d 1369 (11th Cir. 2018)
  • United States v. Richard, et al, 678 F. App’x 927 (11th Cir. 2017)
  • United States v. Clark, 14-12458 (11th Cir. 2014)
  • United States v. Murray, 14-13452 (11th Cir. 2014)
  • Jones v. Astrue, 647 F.3d 350 (D.C. Cir. 2011)
  • Florida Super Lawyers, “Rising Star,” 2020-21
  • “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
  • Harvard Law School Criminal Justice Institute, Fall 2021 Trial Advocacy Workshop, Faculty
  • Federal Bar Association Broward County Chapter, National Delegate and Co-Chair, Diversity & Inclusion Committee
  • Children’s Bereavement Center, Vice-Chair, Board of Directors
  • John Knox Village Foundation, Board of Directors
  • Broward County Sheriff’s Office, Professional Standards Committee, Civilian Member
  • Florida Bar Constitutional Judiciary Committee
  • UNLV Graduate College, Leadership & Social/Entrepreneurship Advisory Board
  • Leadership Florida, Connect Class 11
  • Leadership Fort Lauderdale, Class 26
  • Fort Lauderdale Alliance, Corporate Council and International Action Team
  • 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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