Robert Smalls: The Slave Who Stole a Confederate Warship and Became a Congressman

Robert Smalls circa 1870-1880
Robert Smalls circa 1870-1880
Mathew Brady, Library of Congress/Wikimedia Commons // Public Domain

The CSS Planter
The CSS Planter

It was the spring of 1862, and Robert Smalls—a 23-year-old enslaved man living in Charleston, South Carolina—was desperate to buy the freedom of his wife and children. The asking price was $800.

He had money saved up. Since the age of 12, Smalls had worked odd jobs in Charleston: lamplighter, rigger, waiter, stevedore foreman. At around age 15, he had found work on the city’s docks and joined the crew of the ship CSS Planter. For every $15 he earned, Smalls was allowed to keep $1. The rest of the money went to his owner.

Smalls tried earning extra cash on the side, buying candy and tobacco and reselling it at a higher price. But it was hardly enough. When he asked to buy the freedom of his wife and children, he barely had $100 to his name. He knew, at that rate, the task could take him decades. Smalls had to think of something new—something drastic.

An unwitting bystander might have mistaken Robert Smalls and his wife Hannah Jones for freed slaves. The couple had met when Robert was 16, working at a hotel where Hannah was employed as a maid. They married, had two children, and lived in a private apartment above a horse stable in Charleston. Each day, Robert walked alone to the docks and wharves of Charleston, eventually finding himself work on the CSS Planter.

But appearances of freedom were an illusion. Smalls and Jones had to give nearly all of their income to his owner. Worse yet, the couple was constantly burdened with worry. Smalls knew that his wife and children could be stripped from his life on his owner’s whim. He knew the only way to keep his family together was to buy them.

Born in 1839 behind John McKee’s house, Smalls had grown up as the family’s household favorite (potentially because McKee, or McKee’s son, was his secret father). Whatever the reason, Smalls did relatively limited housework, was allowed inside his owner’s house, and was permitted to play with the local white children.

Smalls’s mother watched her son being coddled and was afraid he’d grow up without knowing about the horrors of slavery, so when Smalls was 10, she dragged her son into the fields. He picked cotton, rice, and tobacco. He slept on dirt floors. He watched slaves in town be tied to a whipping post and lashed. The experience changed him.

Smalls began to rebel. He protested slavery and started appearing more frequently in jail. Eventually, his mother grew concerned for his safety and asked McKee if Smalls could be sent to Charleston to work. Their owner agreed. It was in Charleston that Smalls would discover the woman who became his wife, as well as a talent for sailing.

By the spring of 1862, Smalls was working aboard the CSS Planter, an old cotton steamer-turned-warship. It was the midst of the Civil War, and Smalls helped steer the boat, plant sea mines, and deliver ammunition and supplies to Confederate outposts along the coast. Whenever Smalls looked out toward sea, he saw a blockade of Union ships bobbing on the horizon.

The captain of the CSS Planter, C.J. Relyea—known for wearing a trademark wide-brimmed straw hat—had a crew comprised of multiple slaves. One day, another enslaved crew member grabbed the captain's hat while he was away and planted it on Smalls’s head. “Boy, you look just like the captain,” he said.

Smalls looked out at the ocean, past Fort Sumter and toward the fleet of Union ships in the distance.

He had an idea.

Smalls knew he could steal the Planter. He knew the shipping routes. He knew the checkpoints. He knew the codes and signals to get past the forts. And, of course, he knew how to pilot the boat. As the Planter’s wheelman, Smalls was basically the boat’s unofficial captain.

Late on May 13, 1862, the Planter returned to Charleston from a two-week trip. The white crewmembers were supposed to stay aboard after docking, but the Planter was scheduled to begin another long mission the next morning, and the white crew supposedly missed carousing and sleeping on land. They left the boat for a night out on the town, trusting the enslaved crew would take care of the ship.

It was exactly what Smalls had hoped for.

Around midnight, Robert slipped the skipper’s jacket over his shoulders and ordered the other enslaved crewmembers to light the boilers. At 2 a.m., the CSS Planter eased into Charleston Harbor.

Smalls quietly directed the boat to a rendezvous point where he picked up Hannah, his children, and eight other enslaved people (Smalls had warned his family in advance of the possibility that May 13 could be the fateful night). Hannah later told a reporter that, in his words, “The whole party had solemnly agreed in advance that if pursued, and without hope of escape, the ship would be scuttled and sunk; and … they should all take hands, husband and wife, brother and sister, and jump overboard and perish together.” Her husband was more terse. When she asked what would happen if they were caught, Smalls said, “I shall be shot.”

The crew intended to fight to the death. The boat was loaded with 200 rounds of ammunition and five large guns, including a howitzer and a giant pivot gun. If cornered, they’d dynamite the boiler.

Moonlight glinted off the water. Smalls raised the Confederate and Palmetto flags and pointed the boat at the open ocean. As the Planter approached the first checkpoint, Fort Johnson, Smalls began to pray, “Oh Lord, we entrust ourselves into thy hands.” He sounded a signal on the steam whistle and was waved through. The boat slipped deeper into the harbor.

As the boat approached Fort Sumter, Smalls adjusted the captain’s straw hat and leaned out the pilot-house window. He had watched Captain Relyea pass the fort dozens of times before. He had studied his body language. So Smalls stood on the deck, arms crossed, his face obscured by the hat’s brim and the night’s darkness.

At 4:15 a.m., the Planter sounded the steam whistle again. According to a report filed by the Committee on Naval Affairs, “The signal ... was blown as coolly as if General Ripley [the commander of Charleston’s defense] was on board.”

The guards at Fort Sumter sounded their signal in return: “All right.”

The Planter successfully passed five Confederate gun batteries. Once outside of Fort Sumter’s cannon range, Smalls lowered the rebel flag and raised a white bed sheet. The Planter aimed for the Union blockade.

Seeing a Confederate ship hurtle in their direction, sailors aboard the union USS Onward panicked. It was dusky, and they couldn’t see the surrender flag.

“Open her ports!” Acting Volunteer Lt. J Frederick Nickels ordered. The crew pointed the No. 3 port gun in the direction of the Planter and was ready to fire when somebody aboard cried, “I see something that looks like a white flag!”

The command to fire was dropped. The group aboard the Planter began to dance and sing. As the Planter reached the blockade, Smalls stepped forward and removed his hat. “Good morning, sir!” he yelled. “I’ve brought you some of the old United States guns, sir!”

Within minutes, the stars and stripes were flapping high from the Planter’s mast.

The McKee-Smalls House in Beaufort, South Carolina
The McKee-Smalls House in Beaufort, South Carolina
Wikimedia // Public Domain

Smalls quickly became a folk hero. “If each one of the Generals in our army had displayed as much coolness and courage as [Smalls] did when he saluted the Rebel flag and steamed past the Rebel fort, by this time the Rebellion would have been among the things that were [past],” The New York Daily Tribune wrote. Navy Admiral S.F. Dupont would call Smalls “superior to any who have come into our lines.”

Meanwhile, in South Carolina, a $4000 bounty was placed on Smalls’s head and Captain Relyea was court-martialed, sentenced to three months in prison for negligence (although this was later overturned). The Confederate brass was dumbstruck. They couldn’t fathom that a crew of slaves was clever enough to outfox their navy. (Unable to give the credit, F.G. Ravenel, a Confederate Aide-de-Camp, believed that “two white men and a white woman” must have conspired to make it happen.)

Smalls didn’t care. He was too busy enjoying the freedom and money that he had long been denied. A few weeks after surrendering the ship, the U.S. Congress awarded Smalls and his crew half of the Planter’s value. Smalls received $1500 and an audience with President Lincoln.

At one meeting with Lincoln, Smalls was joined by Frederick Douglass. The famed abolitionist implored the president to allow African-Americans to join the military—and convinced him that Smalls should lead the cause.

Smalls did. He joined the U.S. Navy, revealing the location of enemy mines, and personally recruited about 5000 African-American soldiers. He joined the USS Planter on missions to the south, including an attack on Fort Sumter. During a battle at Folly Island Creek, South Carolina, the Planter’s white captain abandoned his post in despair. Smalls stepped into the pilot-house and led the ship to safety. For his bravery, he was awarded the rank of Navy Captain.

When he wasn’t fighting battles at sea, Smalls was fighting civil rights battles on land. In December 1864, Smalls was tossed out of an all-white streetcar in Philadelphia. Enraged, he used his budding fame to protest the segregation of public transit. Three years later, the streetcars of Philadelphia were integrated.

After the war, Smalls returned to South Carolina with the money he earned and bought his former owner's house.

Not one to rest on his laurels, Smalls helped establish a local school board in Beaufort County and one of the first schools for black children in the region. Then he opened a store. In 1868, he ran for—and won—a seat in the South Carolina House of Representatives, then two years later in the state Senate. In 1872, he started a newspaper called The Southern Standard. And in 1874, he ran to become a representative in the U.S. Congress.

He won 80 percent of the vote.

During five nonconsecutive terms, Congressman Smalls pushed for legislation to desegregate the military and restaurants in Washington D.C. His work successfully led to the opening of the famous South Carolina marine base at Parris Island.

All that time, Smalls kept his mind and heart open. Legend has it that when his former owner’s wife was stricken with dementia, she’d often wander into his house, believing it was still hers. Rather than send her packing, Smalls invited her inside.

In 1915, Robert Smalls died in the same house. Today, it’s a National Historic Landmark.

This story first ran in 2017.

The Ultimate Charles Darwin Quiz

16 Things You Might Not Know About William Shakespeare

Hulton Archive, Getty Images
Hulton Archive, Getty Images

Despite his many contributions to English literature, surprisingly little is known about William Shakespeare’s life. For the past four centuries, historians have had the difficult task of piecing together the Bard's biography with only a handful of old legal documents. Here's what we do know about the celebrated actor, poet, and playwright, who was born (and died!) on April 23.

1. Shakespeare's writing was likely influenced by his father's legal troubles.

When Shakespeare was about 5 years old, his father, John—a glovemaker—was accused of illegal money-lending and wool-dealing by Crown informers. The ordeal plunged the elder Shakespeare into legal troubles that would plague him for the next decade. "William grew to adulthood in a household where his father had fallen in social and economic rank," historian Glyn Parry told The Guardian. Parry argued that the experience likely shaped Shakespeare's attitudes toward power, class, and the monarchy—major themes in his future works.

2. Shakespeare got married because of an unexpected pregnancy.

Shakespeare was 18 when he learned that Anne Hathaway, 26, was pregnant with his first child. The couple quickly decided to marry in November 1582 and greeted daughter Susanna in May 1583. Two years later, they had twins Judith and Hamnet. Unfortunately, Shakespeare has no living direct descendants: Hamnet died at age 11, probably a victim of some disease; Judith outlived her three children; and Susanna had one daughter, Elizabeth, who was childless.

3. Nobody knows what Shakespeare did between 1585 and 1592.

After the birth of his twins, Shakespeare fell off the map for seven years. One unsubstantiated theory (and there are many) suggests that he supported his family by working as a lawyer or legal clerk. Indeed, Shakespeare's plays show an impressive grasp of legal knowledge. "No dramatist of the time … used legal phrases with Shakespeare's readiness and exactness," wrote 19th-century literary critic Richard Grant White. (High praise considering that Shakespeare once wrote, "Let's kill all the lawyers.")

4. Shakespeare was, first and foremost, an actor.

An engraving of Shakespeare by E Scriven, after Humphrey's drawing known as the 'Chandos portrait,' circa 1590.
An engraving of Shakespeare by E Scriven, after Humphrey's drawing known as the 'Chandos portrait,' circa 1590.
Hulton Archive, Getty Images

Shakespeare became an actor at a time when the job was considered downright unsavory. "[A]ctors were already marked as undesirables by England's vagrancy laws, which mandated that traveling troupes had to find aristocratic patronage," John Paul Rollert wrote in The Atlantic. "Rogue players ran the risk of being flogged, branded, and finally hanged." Little is known of Shakespeare's acting chops, but it's believed Shakespeare favored playing "kingly parts," including the ghost in his own Hamlet.

5. Shakespeare may have participated in organized crime.

In the 1590s, many of London's theaters operated as shady fronts for organized crime. (The Lord Mayor of London decried the theater—and specifically plans for the new Swan Theatre, where Shakespeare may have briefly worked—as a meeting spot for "thieves, horse-stealers, whoremongers, cozeners, conny-catching persons, practisers of treason, and such other like.") In 1596, Swan Theater owner Francis Langley accused William Gardiner and his stepson William Wayte of making death threats. Soon after, Wayte retaliated with the same accusations against Langley and—for some reason—William Shakespeare. This has led historian Mike Dash to suggest that Shakespeare may have been involved in some unspoken criminal activity.

6. Shakespeare was a matchmaker (and a marital peace-maker).

It may be no surprise that the author of Romeo and Juliet had a penchant for bringing lovers together: He once helped arrange the marriage of his landlord's daughter. The only reason we know this, however, is because the marriage had a rocky start. When a dispute over the dowry boiled over, Shakespeare had to go to court to act as a character witness for his landlord, whom he called a "very honest fellow." The transcript is the only record of Shakespeare speaking.

7. The first printed reference to Shakespeare as a playwright was an insult.

The first mention of William Shakespeare as a playwright appeared in 1592, when the dramatist Robert Greene (or possibly Henry Chettle) called him an "upstart Crow [who] … supposes he is as well able to bombast out a blank verse as the best of you." (In other words: A jack-of-all-trades, and a master of none.) Future reviewers would offer kinder words; in 1598, the critic Francis Meres called him "mellifluous and honey-tongued."

8. Shakespeare likely helped steal a theater, piece by piece.

In 1596, the Theatre in Shoreditch—where Shakespeare cut his teeth as an actor—went dark. The lease for the property on which it was built had expired, and Shakespeare's acting troupe, the Lord Chamberlain's Men, were forced to take their show elsewhere. Two years later, the former owners hatched a crazy plan to take their playhouse back. One winter night in 1598, a group armed themselves with swords and axes, snuck into the theater, and began dismantling the playhouse piece by piece—although it would take more than one night to demolish it. While there's no evidence that Shakespeare joined the crew, he certainly knew about the raid. Eventually, parts of the playhouse would go into the construction of a new theater just south of the River Thames. Its new name? The Globe.

9. Only one handwritten script of Shakespeare's exists.

Five examples of the autograph of English playwright William Shakespeare, circa 1610.
Five examples of the autograph of William Shakespeare, circa 1610.
Hulton Archive, Getty Images

Anyone interested in studying the Bard's cramped handwriting has only one reliable place to look—the original draft of the Book of Sir Thomas More, a politically-charged play that targeted, in-part, xenophobia in England. Written mainly by dramatist Anthony Munday, the play was completed with the help of four fellow playwrights. One of them, presumed to be Shakespeare, helped write a stirring monologue in which the lead character asks an anti-immigrant mob to imagine themselves as refugees.

Say now the king …
Should so much come too short of your great trespass
As but to banish you, whither would you go?
What country, by the nature of your error,
Should give you harbour?

The play, by the way, would not be performed. Censors believed it could start a riot.

10. Shakespeare might have experimented with drugs.

Shakespeare might have had some, well, experience with drugs. According to analyses by South African scientists, a handful of 400-year-old clay tobacco pipes excavated from the playwright's Stratford garden contained potential evidence of cannabis (although the study authors noted that "Unequivocal evidence for Cannabis has not been obtained"). Other pipes nearby contained remnants of cocaine and hallucinogens. (There's no evidence that any of these pipes belonged to Shakespeare, but it does indicate that "narcotics were accessible" at the time, the Telegraph reports.)

11. Shakespeare may have been a tax cheat.

In the late 16th century, English residents had to pay a tax on personal wealth called a lay subsidy. In 1597, Shakespeare was supposed to pay a tax of five shillings. The following year, he was supposed to pay a larger tax of 13 shillings and 4 pence. Documents show that the Bard never paid the piper. (His reasons are a matter of speculation, but it could have been a clerical error because he'd already moved away from the parish.)

12. Shakespeare was a grain hoarder.

According to the UK Parliament, between 1604 and 1914 over 5200 enclosure bills were enacted, which restricted the use of vital, publicly-used farmland. Ensuing riots in 1607, called the Midland Revolts, coincided with a period of devastating food shortages. It appears that Shakespeare responded to the situation by hoarding grain. According to the Los Angeles Times, he "purchased and stored grain, malt and barley for resale at inflated prices to his neighbors and local tradesmen."

13. The Globe Theatre burned down during a performance of one of Shakespeare's plays.

An 1647 engraving by Hollar of Shakespeare's Globe theatre.
An 1647 engraving by Hollar of Shakespeare's Globe Theatre.
Rischgitz, Getty Images

On June 29, 1613, a prop cannon caused a fire at the Globe Theatre during a performance of Henry VIII. Sparks landed on the thatched roof and flames quickly spread. "It kindled inwardly, and ran round like a train, consuming within less than an hour the whole house to the very ground," a witness Sir Henry Wotton claimed. According to The Telegraph, "the only reported injury was a man whose flaming breeches were eventually put out using a handy bottle of ale."

14. Shakespeare laid a curse upon his own grave.

When Shakespeare died in 1616, grave-robbing was extremely common. To ensure he'd rest through eternity peacefully, the Bard is believed to have penned this curse, which appears on his gravestone.

Good frend for Jesus sake forbeare,
To digg the dust Encloased heare:
Bleste be [the] man [that] spares these stones,
And curst be he [that] moves my bones.

Unfortunately, somebody apparently ignored the dead man's foreboding words. In 2016, researchers scanned the grave with ground-penetrating radar and discovered that grave robbers might have stolen Shakespeare's skull.

15. Shakespeare's legacy has killed a lot of trees.

And we're not just talking about the millions of copies of books that have been printed with Shakespeare's name on them. In 1762, an anonymous magazine writer claimed that a drunken Shakespeare, after an evening out on the town, once spent the night sleeping under a crabtree in Bidford-upon-Avon. The story is probably a legend, but that never stopped souvenir-hungry Shakespeare lovers from flocking to the famed crabtree and picking it to pieces. By 1824, the tree was nothing but a stump and had to be uprooted.

16. Shakespeare's legacy lived on thanks to two fellow actors.

The cover of a 1623 collection of Shakespeare's works.
Rischgitz, Getty Images

Shortly after Shakespeare died, two of his longtime friends and colleagues—John Heminge and Henry Condell—edited Shakespeare's plays and collected them in a 1623 book titled Mr. William Shakespeares Comedies, Histories, & Tragedies. That same book, now called the First Folio, helped preserve Shakespeare's work for the coming generations and is widely considered one of the most significant books printed in English.

This story was first published in 2018.

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