When you think of Leesburg, Florida, world-class, boundary-pushing jazz probably isn’t the first thing that comes to mind. Grammy-nominated trumpeter Theo Croker flips that notion on its head.

A Leesburg native, Croker is the grandson of legendary jazz figure Doc Cheatham — a trumpeter whose career spanned generations. His father, William Henry Croker, was a civil rights activist and high school principal, while his mother, Alicia Cheatham, worked as a guidance counselor. Together, that foundation set a trajectory that would take him far beyond the Lakefront City.

If Leesburg provided the roots, the world provided the ascension.

After training at Douglas Anderson School of the Arts in Jacksonville and later studying at the Oberlin Conservatory in Ohio, Croker didn’t just follow in his grandfather’s footsteps. He stepped outside of them.

A seven-year residency in Shanghai, China became a turning point — a stretch that pushed him beyond the rigid expectations of the American jazz scene and into something more expansive. It’s where he began to develop what he’s described as a “polyglot” sound, pulling from multiple musical languages to find his own voice.

It’s a fearless approach to the genre that mirrors his father’s legacy of advocacy. For Croker, pushing the boundaries of jazz isn’t just an aesthetic choice — it’s a form of musical activism. He has often described his work as a “reclamation” of Black culture, using his trumpet to narrate stories of identity and ancestry that refuse to be boxed in by tradition.