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 American Civil War, Gleaves relocated to Beaufort, South Carolina. He then partnered with Robert Smalls, a former slave who had commanded a vessel he seized from the Confederates during the conflict.