One notable figure in Black history known as Pilot was Robert Smalls, who was an enslaved African American man in South Carolina. In 1862, Smalls famously commandeered a Confederate transport ship named the CSS Planter and sailed it through Confederate-held waters to the Union blockade, where he and his fellow enslaved crew members surrendered themselves to the Union Navy.

Smalls' bold actions not only gained his freedom but also provided valuable intelligence to the Union Army and Navy. He went on to serve in the Union Navy and later became a prominent figure in South Carolina politics during the Reconstruction era, advocating for civil rights and social reform.

Robert Smalls' story is a testament to the resilience, bravery, and tenacity of enslaved individuals who fought for their freedom and contributed significantly to the advancement of Black Americans in history.