Jonathan K. Osborne - Jonathan K. Osborne

Always an Athlete

It was all a dream: after graduating from Georgetown Law, I started my career at Gunster Law Firm. After a couple years, I left private practice for my dream job, serving the United States of America as a federal prosecutor in Miami, my hometown.

In 2019, I returned to Gunster where I practice business litigation and lead our firm’s white collar litigation practice with matters across the state of Florida.

I played college basketball at UNLV and the University of Alaska—and now train with skills coach David Gartrelle, founder of Big City Basketball.

In 2025, I launched the Always an Athlete podcast.

By Serving, We Lead.

My experience as a federal prosecutor reinforced the importance of leadership, responsibility, and service to others. Beyond my legal practice, I remain committed to mentoring young professionals the way my mentors have guided me along the way.

“A visionary faith leader once said, when you have a banquet do not invite your friends or rich neighbor, if you do, they may invite you back, and you’ll be repaid.
No, instead, invite the underrepresented and the underserved, and you will be blessed.

That leader was not talking about corporate America, he was talking about servant leadership.

As I stand here . . . what I can assure you is I owe everything that I have accomplished—as a leader and a professional—to hard work and inspiration from leaders ahead of me on this path, who reached back to extend me an invitation. These invitations, to the family dinner table, to a business meeting, or even just on a walk to get a coffee, have changed my life, over and over, again.

And my question for each of you is: who is invited to your table?”