The Slave Who Captained the Ship to His Freedom

By David A. Carrino, Roundtable Historian
The Cleveland Civil War Roundtable
Copyright © 2015-2016, All Rights Reserved

Editor’s note: This article was the history brief for the February 2016 meeting of the Cleveland Civil War Roundtable.


There is an old joke that is intended to convey the lesson that in order for a person to attain a particular goal he needs to do more than simply petition the Almighty and then let God decide whether or not this goal should be realized. As this joke goes, a man died and went to heaven, and when he came face to face with the Sovereign of the Universe, he said to God, “I am certainly happy to be here in heaven, but there is a question that I have long wanted to ask you. During my life on earth I prayed to you every day, often more than once per day, that you would let me win the lottery. But even after years of praying, I never won the lottery. The Bible says that if someone asks, it will be answered, yet you never answered my prayer to win the lottery.” God looked compassionately at the man and in a gentle voice said, “My son, it was always my desire to see you be happy, but that was one prayer that I was not able to answer.” The man replied, “You are God almighty. How could you not have been able to answer that prayer?” God responded, “Even with all my almighty powers, I was not able to answer your prayer to win the lottery, because you never bought a lottery ticket.” Just as the old joke admonishes that more must be done to address personal needs and desires than simply prayerfully await intervention by the Almighty, a slave named Robert Smalls did not merely wait for his freedom to come to him, but won his freedom in a unique and daring escape.

Robert Smalls

Robert Smalls was born on April 5, 1839 in Beaufort, South Carolina. Smalls was born behind the home of John McKee, who was the owner of Robert Smalls’ mother. The identity of Smalls’ father is not known with certainty, but it may have been John McKee’s son, Henry. Smalls’ mother, Lydia, worked in the house that the McKee’s had in the city, but the McKee family also owned a plantation on an island near Beaufort. For reasons that are unclear, Robert Smalls was favored as a slave, and he was allowed to play with white children and work at less strenuous tasks. Because of this, Smalls’ mother worried that her son would fail to fully grasp the horrible realities of slavery, and she arranged for Robert to spend time at the McKee plantation. It was here that Robert saw the rigors of field work and the cruelty of whippings. As a result, Robert learned what bondage truly meant for a slave, and he developed a spirit of defiance.

When Smalls reached the age of 12, he was hired out to work in Charleston. Smalls worked at a number of jobs in Charleston and eventually began to work on the docks. This led to him working on harbor boats, and he showed such a keen aptitude for this work that he became what was called a wheelman, which was essentially a pilot, although blacks were not allowed to hold the title of pilot. In this role Smalls became thoroughly familiar with the waters of Charleston harbor and along the coast. Several years after he began working in Charleston, Smalls married Hannah Jones, who worked in a Charleston hotel, and they had two children. When the Civil War began, Smalls’ experience as a wheelman led to his assignment on the Confederate ship CSS Planter. Prior to the war the Planter was a cotton steamer. For her wartime role she was armed and used to transport supplies to forts in and around Charleston harbor. The Planter was manned by three white crewmen and eight black slaves with Smalls acting essentially as the boat’s pilot.

The Planter

On the fortuitous night of May 12, 1862 Smalls set in motion a plan that he had devised some time earlier and had kept in mind for just the opportunity that presented itself that night, even though that plan almost certainly meant death for all the participants if it failed. On the night of May 12, 1862 the three white crewmen of the Planter, Captain C.J. Relyea, pilot Samuel H. Smith, and engineer Zerich Pitcher, took it upon themselves to take unauthorized shore leave. After they were gone, Smalls took command of the Planter and steamed away from the wharf where she was docked. The Planter then steamed to another wharf where Smalls’ wife, two children, and several other slaves were picked up. With its party of nine men, five women, and three children, the Planter steamed through Charleston harbor under the guidance of Robert Smalls, whose meticulous knowledge of those waters gave him the exact skill needed for the escape voyage. Smalls also donned the captain’s large straw hat to conceal his face and used his familiarity with the captain’s signals and mannerisms to deceive any Confederate sentries whom he encountered along the escape route, which included passage near Fort Sumter. At the appropriate points along the way, Smalls blew the Planter’s steam whistle to give the usual salute and even mimicked the captain’s posture while he stood on board. At every checkpoint the boat was allowed to pass without incident. Once out of the harbor, the Confederate flag on the Planter was replaced with a white sheet that Smalls’ wife Hannah had taken from the hotel in which she worked, and the boat steamed toward the Union blockading fleet. The first Union ship that the Planter encountered was the USS Onward, but initially men on board that ship did not see the white flag and aimed some of the ship’s guns at the Planter. But soon the white flag was seen, and the escaped slaves were taken on board the Onward.

The daring escape that Smalls led was reported throughout the North in newspapers such as Harper’s Weekly. For the Confederacy the escape was an embarrassment, primarily because the ingenious plan and its execution contradicted the Confederacy’s firmly held claim that blacks were intellectually inferior and lacked initiative. In fact, some in Charleston insisted that Smalls and his party must have had assistance from whites in order to devise and carry out such a resourceful escape. Smalls’ fame led to this former slave meeting the president of the United States, Abraham Lincoln, and Smalls added his voice to that of Frederick Douglass in urging Lincoln to allow blacks to fight against the Confederacy. In October 1862, five months after his escape, Smalls returned to the area around Charleston to serve as pilot of the Planter, which was now being used as a Union gunboat, and he participated in 17 military engagements. Most exemplary was the action at Folly Island Creek near Charleston, where the captain of the Planter was overcome by fear in the heat of an intense fight and hid in the coal bunker. Smalls took command of the boat and guided it to safety.

The Robert Smalls House, which was formerly owned by the McKee family
The house is a National Historic Landmark.
Robert Smalls, later in life

After the Civil War Smalls used the money that the U.S. government awarded to him for the capture of the Planter to purchase the house in Beaufort that had belonged to his former owner. Not only did Smalls and his family reside there, but Smalls allowed Jane McKee, the widowed wife of his former owner, to live in the house until her death. Smalls later went into politics and served in the South Carolina House of Representatives and Senate and the U.S. House of Representatives. His most noteworthy political service came at the 1895 South Carolina constitutional convention, where the re-emerged white supremacists sought to undo the civil rights that had been established during Reconstruction. In an impassioned speech against the proposed South Carolina constitution, Smalls gave a stinging reproach to the ex-Confederates who were laying the foundation for Jim Crow when he stated, “I fought in seventeen battles to make glorious and perpetuate the flag that some of you trampled under your feet.” Although Smalls was unsuccessful in blocking passage of the new South Carolina constitution, it has been said that he showed as much courage in opposing that constitution as he did during his escape on the Planter.

The Logistics Support Vessel Maj. Gen. Robert Smalls

Robert Smalls died on February 22, 1915 in the house behind which he had been born into slavery, the house in which he had worked as a slave, which he came to own as a free man, and which now is on the National Register of Historic Places. Another legacy of Robert Smalls is the first U.S. Army ship named after an African-American. This ship was launched in 2004, and in light of the time that Smalls spent on a boat that was used to transport supplies in Charleston harbor, it is fitting that the U.S. Army vessel that bears Smalls’ name is used for transport of cargo and vehicles. Robert Smalls lived a life that allowed him to say with absolute conviction, “My race needs no special defense for the past history of them and this country. It proves them to be equal of any people anywhere.”

There are many inspirational stories in the Civil War, in fact probably more than are known, because in all likelihood some inspirational Civil War stories tragically were not recorded. Fortunately, the story of Robert Smalls was recorded, because his story is inspiring not only from the standpoint of slavery, but also from the perspective of a person taking matters into his own hands and doing whatever he can to reach his goal no matter the risk. Robert Smalls did not simply buy a ticket on his ship to freedom. Robert Smalls, both figuratively and literally, was the captain of the ship to his freedom. Good things come to those who wait? This is not an axiom to which Robert Smalls adhered. Robert Smalls lived by the axiom that God helps those who help themselves.