Jonathan K. Osborne was born in Miami, Florida, to mother, Leslie and father, David. Growing up, Jonathan was shown firsthand the value of public service by his grandparents, Albert and Virginia Tresvant.

A public speaker from an early age, Jonathan believed since he was very young that he would become a lawyer. He is now the managing shareholder of the Fort Lauderdale Office of Gunster Law Firm, and the chair of its white-collar defense and internal investigations practice. He is a first-chair trial lawyer who has tried business cases to verdict in court and arbitration, handling all aspects of trial from jury selection to closing argument and appeal. Known to carry Gatorade with him around the courtroom during jury trials, one of Jonathan’s dear friends and colleagues nicknamed him the “Trial Athlete,” which is fitting because as early as Jonathan discovered public speaking, he discovered sports. 

In middle school at Ransom Everglades, Jonathan played football, basketball, and ran track. Later, at the Ransom Upper School, Jonathan continued with football and basketball and joined the volleyball team. In 2000, the Osbornes moved to Las Vegas and Jonathan finished high school at Green Valley High School, in Henderson, Nevada. At Green Valley, Jonathan focused on basketball and was recruited by Coaches Charlie Spoonhour and Dave Rice to play basketball for the Runnin’ Rebels of UNLV.

Way back then, the UNLV media guide listed his ambitions as becoming either a criminal defense attorney or an NBA player—at least one of those dreams came true.

After 2 years at UNLV, Jonathan sat out one year before transferring to the University of Alaska-Fairbanks, where he started at shooting guard, graduating in 2006. After graduation, Jonathan went on graduate school at UNLV, where he studied communication and taught public speaking courses. His papers won awards at national communication conventions. While in law school at Georgetown University in Washington, D.C., Jonathan argued an appeal before Circuit Judges Merrick B. Garland, Janice Rogers Brown, and A. Raymond Randolph, of the United States Court of Appeals for the D.C. Circuit, resulting in a published opinion in his client’s favor. He also competed nationally in moot court and was a three-time intramural basketball champion.

In 2011, Jonathan graduated from law school and moved back to Florida where he began his career at Gunster, Yoakley & Stewart, a premiere Florida business law firm. In the early years, Jonathan focused on litigation between businesses. In the community, Jonathan served as a mentor for Habitat for Humanity families and co-founded “YP,” a faith-based leadership training program from young professionals, hosted at First Baptist Church of Fort Lauderdale. 

After about 3 years, Jonathan moved from Broward back to his hometown, Miami, to join the United States Department of Justice as a federal prosecutor. While a prosecutor, Jonathan focused on white collar crime, fraud, and transnational organized crime, including cartels. He prosecuted the second-ever case indicted under the Kingpin Act, alleging violations of OFAC regulations and money laundering against U.S. persons and a Colombian Specially Designated Blocked Person; investigated Florida companies for wire fraud and conspiracy, and investigated corrupt politicians, doctors, and pharmacies. He also saw the U.S. Constitution at work each day, through the interplay of the law, Courts, government, and private parties; and the marvels of our jury trial system.

Always a dedicated mentor, in 2016, Jonathan founded “LEOs Live Miami,” a program that featured monthly career days and field trips for students from two magnet schools. Guest speakers included federal judges, prosecutors and defense attorneys, and federal and local law enforcement.

In his nearly five years as a prosecutor, Jonathan led investigations with the following federal and state agencies.

• • United States Department of Justice
    • Federal Bureau of Investigation
    • Drug Enforcement Administration
    • Bureau of Alcohol, Tobacco, Firearms & Explosives
    • United States Marshals Service
    • Office of International Affairs (OIA)

• • Department of Homeland Security
    • Federal Protective Service
    • Department of the Coast Guard
    • United States Customs & Border Protection
    • Homeland Security Investigations
    • United States Secret Service
    • United States Citizenship and Immigration Services

• • United States Postal Service

• • Social Security Administration – Office of Inspector General

• • Department of the Treasury
    • Office of Foreign Assets Control (OFAC)
    • Financial Crimes Enforcement Network (FINCEN)
    • Internal Revenue Service – Criminal Investigation Division

• • U.S. Embassies in Jamaica, Mexico, Haiti, Colombia, Chile, and France

• • British High Commission of Jamaica

• • Office of the Colombian Attorney General
  • Miami-Dade, Broward, and Palm Beach County State Attorneys’ Offices

• • Florida Department of Law Enforcement (FDLE)

• • City of Miami Police Department

• • Miami-Dade County Sheriff’s Office

• • Broward County Sheriff’s Office

• • City of Fort Lauderdale Police Department

• • Pembroke Pines Police Department

• • Hialeah Gardens Police Department

• • City of Hialeah Police Department

• • Miami Gardens Police Department

• • City of Opa-Locka Police Department

• • Miami Beach Police Department

• • Monroe County Sheriff’s Office

• • Aventura Police Department

• • Coral Gables Police Department

• • Florida City Police Department

• • Homestead Police Department

• • Miami-Dade Schools Police

Jonathan’s current involvement in South Florida’s legal community includes serving for several years on the Board of the Federal Bar Association Broward Chapter, of which he is currently the President-Elect. In 2024, Jonathan was appointed by Governor Ron DeSantis to a four-year term on the Judicial Nominating Commission for Florida’s Fourth District Court of Appeal. And for several years, Jonathan has served on Federal Magistrate Merit Selection Panels Regarding Magistrate Judge Vacancies in the Southern District of Florida.

At Gunster, Jonathan co-founded the firm’s Leadership Training Academy which provides leadership and legal training to Florida’s law students.

He has received numerous awards, including:

• South Florida Business Journal, 40 Under 40 Honoree, 2024

• Florida Super Lawyers, “Rising Star,” 2020-24

• The Best Lawyers in America®, “Ones to Watch,” Criminal Defense: White-Collar, 2023-26

• Haitian Lawyers Association, Presidential Award for Outstanding Service in the Community, 2024

• Volunteer of the Year, U.S. Attorney’s Office, 2017

Teaching Experience

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

• Florida State University College of Law Juris Master Program, 2022-2023

• Emory University School of Law, Trial Advocacy Program, 2024

Community Service

• Children’s Bereavement Center, Former Board Chair

• Federal Bar Association Broward County Chapter, President, 2025

• Broward County Sheriff’s Office, Professional Standards Committee, 2021-2025

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

• Florida Bar Constitutional Judiciary Committee (Term 2024)

• Leadership Fort Lauderdale, Class 26