One significant figure in Black history known as Pilot was Robert Smalls, who was born into slavery in South Carolina in 1839. Smalls managed to escape slavery by commandeering a Confederate transport ship, the CSS Planter, in Charleston Harbor in May 1862. In a daring and courageous act, he and a small group of enslaved crew members navigated their way past Confederate checkpoints and ultimately surrendered the ship to Union forces. This bold action not only gained freedom for Smalls and his fellow slaves on board but also provided critical intelligence to the Union military.

Following the Civil War, Robert Smalls went on to have a successful political career, serving as a member of the South Carolina House of Representatives and the U.S. House of Representatives. He was a strong advocate for civil rights and played a key role in the Reconstruction era, fighting for voting rights and equal protection under the law for African Americans. Smalls' life story is a powerful example of resilience, courage, and leadership in the face of adversity.