Having led a sea-faring life to some extent, the early part of the war found him employed as pilot of the Rebel transport Planter.

He was thoroughly familiar with the harbors and inlets of the South Atlantic coast.

On May 31, 1862, the Planter was in Charleston harbor.

All the white officers and crew went ashore, leaving on board a colored crew of eight men in charge of Smalls.

He summoned aboard his wife and three children and at 2 o'clock in the morning steamed out of the harbor, passed the Confederate forts by giving the proper signals, and when fairly out of reach, ran up the Stars and Stripes and headed a course for the Union fleet, into whose hands he soon surrendered the ship.