But appearances deceived. At some time in April 1862 Smalls began planning an escape. When the Union army took Port Royal the previous November and extended influence over the surrounding area, nearly all the white residents fled. But most of their slaves, including Smalls’ mother, had stayed. From the mysterious slave ‘telegraph,’ Smalls heard that his mother was in her old home in Beaufort, happily engaged as a cook for Union troops. After General Hunter had assumed Union army command at the end of March, the same telegraph brought news that he was disposed to emancipate slaves. Smalls decided Beaufort would be more suited than Charleston for rearing his children.

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One of Smalls’ fellow crewmen jokingly suggested they should steal the Planter. Smalls told him the possibility was no joke. Cautiously, he sounded out others of the crew, save for one who could not be trusted and was left out of the venture. At meetings at Smalls’ home a plan matured.

Opportunity beckoned, when the boat was wharfside at night and the officers left her in Smalls’ care. the wheelman intended to use an excuse to get the distrusted crewman away from the Planter. His own wife, four other women, his two other children, and another child would go aboard another boat moored nightly at a nearby dock. There, a slave sailor, brought in on the plan, would secret them. Then on the Planter’s approach the women, children, and sailor would join the escape party. The only question Smalls and his conspirators had was when to make their break.

That question was answered at the end of the day on May 12. By late afternoon the Planter had been loaded with cargo for delivery to one of the harbor batteries at high water, 6:00 the next morning. The wharf’s guard expected the boat to shove off early. And when the boat’s officers were leaving at day’s end, Smalls was instructed to get ready for the early move. Dutifully he responded, ‘Aye, aye, sir!’

As soon as the officers were gone, Smalls and his fellows consulted and all agreed: the time had come. Word was sent to the sailor on the other boat and to the women and children: proceed. Quietly, on the Planter, Smalls broke into the cabin to secure the captain’s straw hat and jacket and any small arms he could find. It was firmly understood among the conspirators that if they met with any interference they would resist and, if it came to that, rather than suffer capture, they would sink the Planter and all aboard. If scuttling failed, they ‘would all take hands…and jump overboard and perish together.’

At about 3:00 a.m., the boat’s steam engine was fired up. Smoke from the stack was blown toward the city. For a short time Smalls feared that someone would think there was a fire near the wharf and sound an alarm. But all remained quiet. When steam pressure was up, the boat’s Confederate banner and Palmetto flag were hoisted, and the regular wharf signal blown. In her usual manner, the boat got under way, with Smalls at the captain’s post, taking care to imitate that worthy’s well-known posture.

The Planter sailed to the boat where the women and children were stowed, stopped briefly to pick up the waiting party in the darkness, and turned seaward, sailing on at slow speed, giving the prescribed signals along the way. She reached Sumter at the normal time harbor traffic began.

Smalls had the captain’s hat pulled low, his face averted. He pulled the cord for two long whistles and a short one, as vessels were supposed to do. Permission to pass was signaled from Sumter, and the Planter slowly sailed on, seemingly toward the outer forts. But after getting well beyond Sumter, she abruptly picked up speed and swung away, not toward the outer forts, but toward the harbor’s bar and the distant blockaders. As she speeded on, Rebel flags came down and up went a white sheet Smalls took from the boat’s bunk. So it was that a new day dawned for 16 slaves.

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