Grandy, born a slave, captained freight boats on the Dismal Swamp Canal and bought his freedom three times before he finally gained it. He became involved in Boston abolitionism and ultimately appeared before the General Anti-Slavery Convention in London in 1843. As a child, Maffitt was sent from his North Carolina home to a northern boarding school, and at thirteen he was appointed midshipman in the U.S. Navy, where he had a distinguished career. After North Carolina seceded from the Union, he enlisted in the Confederate navy and became a legendary blockade runner and raider. Both Grandy and Maffitt made names for themselves as they navigated very different routes through the turbulent waters of antebellum America.