Even though Robert Smalls was born in 1839, poor, black, and a slave in the Antebellum South, his existence was anything but predictable. His incredible fight to freedom and subsequent life merit the accomplishments of three lifetimes. During a harrowing historical period of intense fear and racism in America, Smalls managed to dramatically turn his life around to one of freedom and success.

Robert Smalls was born in a slave cabin behind the house of his master, Henry Mckee in Beufort, South Carolina in 1839. It has never been confirmed, but many believe his master’s oldest son was, in fact, Smalls’s biological father. Perhaps because of his secret parentage, Smalls lived comfortably in the McKee house and enjoyed some privileges the other slaves were not allowed. He was even known to stay out past evening curfew to hang out with his white friends, much to his mother’s dismay. Even so, Smalls was trapped in a vicious cycle of racism and oppression.

When Smalls was just 12 years old, McKee sent him to Charleston to be hired out as a laborer, with all the money being paid to his master. He worked in a hotel and as a public lamplighter, before finding his love of the sea and a job on the wharves. Smalls became a dockworker, rigger, and sail maker, and he eventually worked his way up to wheelman– although the title was never officially granted to him because of his race. As a result, he became a bit of an expert on the running of Charleston Harbor. At 17, Smalls married Hannah Jones and proceeded to have two children, one of whom died as a toddler. Although life was relatively stable for the Smalls family and the sweet promise of emancipation was in the air, the yoke of slavery remained painfully tight.

The American Civil War broke out in April of 1861 with the Battle of Fort Sumter, very near to Charleston Harbor. The area became a military hotbed, and Smalls was assigned to steer an armed Confederate ship called the CSS Planter. The ship’s duties were to deliver troops, supplies, dispatches, and to survey the surrounding landscape. During this time, he gained an even greater level of responsibility and control, often piloting the Planter through deep reaches of the river, where Federal blockade ships could be seen in the distance. As he manned the helm of the Confederate ship, Smalls could literally see the Union army with own eyes and knew there must be a way to reach them, to reach freedom.

After covertly discussing the matter with the other slaves in the crew, the men decided to risk it all for a shot at escape. One evening in 1862, after having transported guns to a fort in Charleston Harbor, the Planter docked as usual in the wharf, and the three white officers retired ashore for the night, leaving the black crew on board to watch the ship.

Smalls immediately donned a captain’s uniform and backed the Planter out of the harbor, sailing the Confederate boat past a previously established meeting point on the wharf, where he picked up his family and those of the other crewmen.

Dressed from head to toe as the captain, Smalls managed to guide the ship past five different Confederate harbor forts without being noticed by offering the correct signals at each point. The men on shore just assumed he was the captain. He sailed right past Fort Sumter, where the battle for freedom was raging and headed right towards the Union Navy fleet. Thinking Smalls was the enemy, the Northerners came very close to firing on him until they noticed the white sheet he was flying in surrender. His family members and those of his crew were finally safe in the hands of the Union!

Smalls quickly became known in the North as a brave and heroic man. He was awarded prize money for having delivered the Confederate ship filled with revealing documents and valuable weapons to the Union, and these flattering reports made it all the way to Lincoln himself. Smalls felt strongly about supporting the cause and petitioned Lincoln to allow African Americans to enlist in the Union forces at Port Royal, which he eventually did.

Smalls was eager to serve in the military himself and began working as a civilian in the Navy until he was finally allowed to transfer to the Army towards the end of the war. Smalls not only served as a soldier in a black regiment, but he spent his time as captain of the Planter and as a spokesperson for racial justice.

Once the war was over, Smalls learned he was never officially commissioned in the Army because of his race, and he had to fight to receive any sort of Navy pension. After much aggravation, he was finally given a percentage of what he was owed and returned home to his birthplace in Beaufort. At this point, Smalls was fairly comfortable in his own right, and when he realized the home of his former master, Henry McKee, was for sale, he immediately purchased it. 

Because the McKees had refused to pay taxes during the war and effectively lost their property, they were basically destitute. Although “just desserts” would be a tempting outlook for most, Smalls was a deeply compassionate man and allowed his former master’s elderly wife to reside in the home until her death. He spent the next year finally learning to read and write, began a school for African American children, and established a local newspaper.

Smalls was a great admirer of Lincoln and the Republican party, who had “unshackled the necks of four million human beings.” His wartime fame and local connections gave him a shot at a political career, and he was elected to the South Carolina House of Representatives in 1868. He worked effectively to pass Civil Rights legislation and eventually continued on to the Senate, where he became a notable speaker and debater.

Although Smalls had an illustrious career as a soldier, speaker, politician, and activist, he was charged and convicted of taking a bribe in 1882 and lost his position in the Senate. He was sentenced to three years in prison but was pardoned as part of a political agreement. After his first wife’s death a year later, Smalls eventually remarried and stayed active in his beloved Beaufort community. He eventually became sick with malaria and diabetes, passing away at the age of 75 after a long and adventurous life.

And the rest is history.