In 1866 following the American Civil War, Gleaves moved to Beaufort, South Carolina. There he went into business with Robert Smalls, a former slave who during the war had captained a ship that he took from the Confederates.
In 1866, following the end of the American Civil War, Gleaves established himself in Beaufort, South Carolina. He then collaborated with Robert Smalls, a freedman who had seized a ship from Confederate forces during the conflict.