Robert Smalls: The Story of How an Escaped Slave Became a Legend

Buck Stewart
Feb 17, 2019 · 7 min read

Robert Smalls placed the stolen captain’s hat atop his head. Staring into the darkness, he must have wondered if he was a fool to attempt such a plan. Too late to turn back now. The crew, several other enslaved men, waited for orders from their leader. Each ready to claim their freedom.

Smalls stood silhouetted against the night sky at the wheel of the noisy South Carolina steamer, the Planter. The crew cast off from the dock. Their ship filled to the brim with Confederate weapons.

The makeshift captain, if caught, would meet certain death.

The Plan

Captain Relya would occasionally leave the enslaved black crew on board the Planter, while he and the other white officers went home to their families. On May 12, the officers disembarked from the ship and headed to town. Smalls informed his crew-mates the time was now.

Smalls, wearing Captain Relya’s hat, hoped that from a distance he would appear as if he were the white captain piloting the Planter on official duty.

The crew made haste with the plan to sail to the Union blockade at Charleston Harbor. There they would surrender the Planter and it’s weapons to the Union forces. All they would ask for in exchange is their freedom.

Smalls’ wife Hanna and his children, Elizabeth and Robert Jr., waited upriver. The fear of capture undoubtedly weighing heavily on their minds.

Hanna and the children crouched still in the night on another steamer docked on Cooper River. The Planter crept alongside, and without coming to a full stop, Smalls’ family emerged from hiding and stepped aboard.

The steamer continued its sluggish movement toward Fort Sumter, South Carolina. The same fort where the first shots of the Civil War were fired a year prior.

The waters remained the most heavily guarded in the area. The slightest detection that something was amiss would mean instant decimation of the Planter.

Robert Smalls

Robert Smalls was born behind his owner’s home in Beaufort, South Carolina, in 1839. Smalls’ mother, Lydia Polite, raised him. He never knew his father, though many speculated it was likely the plantation owner’s son, Henry McKee.

Smalls spent the previous years working in various capacities as a “hotel waiter, hack driver, and rigger.” He married Hanna Jones, an enslaved hotel maid who worked in Charleston. In 1861, Smalls was assigned to the Planter where he learned to sail and navigate, a skill that would ultimately give him the opportunity to seek his freedom.

The Planter

Accounts of Smalls’ life consistently make note of his bravery. That bravery was perhaps no more evident than it was on the night of the Planter’s covert voyage.

As the rest of the crew trembled while they made their way toward the Union-guarded waters, Smalls showed no signs of a wavering constitution. Smoke floated upward from the stack with no regard for the secrecy of the mission. Smalls knew it was impossible for the Planter to remain undetected, but he stayed confident.

He raised the appropriate flags, the Confederate Stars and Bars, and the South Carolina state flag. A sentry watched the ship depart from the harbor, but he did not sound the alarm. Smalls encountered five distinct checkpoints, where he would provide the necessary Confederate signals, allowing the Planter’s passage.

The Planter cautiously floated toward the Union blockade. A Union ship, the Onward, prepared to fire at the stolen steamer. Smalls ordered the crew to lower the flag and replace it with a white bed sheet to signal their surrender. The Onward held its fire.

The captain of the Onward allowed the crew on board, where Smalls announced he had brought the ship and the stockpile of weaponry to the Union.

A sigh of relief.

Smalls, his crew, and his family had reached freedom.

The Planter


If Smalls story were to end with the Planter’s journey through the darkness, his life would be nothing short of legendary. However, Smalls’ legend was only beginning.

After gaining his freedom, Smalls became a celebrity. Union propaganda, meant to demoralize the South, highlighted his achievement.

Smalls used his celebrity to lobby Secretary of War Edwin Stanton to enlist black soldiers and may have influenced President Lincoln’s approval on the matter. Following the President’s authorization, reports indicate Smalls personally recruited nearly 5,000 black troops. He then joined the Union forces himself, which enlisted him to pilot the ironclad Keokuk.

In the Battle for Fort Sumter, Smalls piloted the Keokuk on its final voyage. He masterfully continued the Keokuk’s assault despite a battery from Confederate cannons. After taking nearly 90 rounds of fire, it could endure no more.

Following Smalls’ show of heroics on the Keokuk, the Union Navy assigned him to his old friend, the Planter. Ever fearless, Smalls’ advanced the Union campaign “in nearly 17 engagements” during his military career.

Following the war, the South Carolina militia awarded him a commission as a brigadier general. He returned to Beaufort where he purchased his former owner’s home in a tax sale using the money he received for delivering the Planter to the Union. There, Smalls dabbled in various ventures, starting a school for black children, publishing a newspaper, and opening a store.

In 1864, he became a delegate to the Republican Convention, beginning his political career. During this period, Smalls was removed from an all-white streetcar in Philadelphia. His fame increased after leading a boycott of the public transportation system in response. In 1868, Smalls won his first elected seat in the state house of representatives. He then won a seat in the state senate from 1870–1874, before winning a seat in the US Congress.

Robert Smalls House, South Carolina


Smalls famously said, “My race needs no special defense, for the past history of them in this country proves them to be equal of any people anywhere. All they need is an equal chance in the battle of life.” It is that equal chance that Smalls continued to fight for throughout his political career.

He faced violent elections over the next several years against the white supremacist redshirt political party. Smalls beat out redshirt delegate George D. Tillman with 52% of the vote in an election that required troops to protect voting centers from violence. Tillman contested the results.

According to the House of Representative’s archives, following the election, “The Democratic South Carolina state government charged Smalls with accepting a $5,000 bribe while chairing the printing committee in the state senate. Smalls arrived in Columbia on October 6, 1877, to face trial. On November 26, he was convicted and sentenced to a three–year prison term. Republican newspapers cried foul, accusing Democrats of targeting the “hero of the Planter” because of his success as a black Representative. After three days in jail, Smalls was released pending his appeal with the state supreme court.”

In 1879, South Carolina governor William Simpson pardoned Smalls for the alleged bribe. Consequently, Smalls continued his political career through 1913 when he finally stepped down after Woodrow Wilson, a member of the Democratic Party, entered the White House. Smalls died soon after in 1915 of natural causes.

According to the University of South Carolina, “Smalls’ contributions to political, economic and education reform in South Carolina were so significant that in 1976, during the celebration of the Nation’s Bicentennial, Governor Edwards issued a proclamation setting aside February 22, 1976, as Robert Smalls Day in the entire state of South Carolina.”

The Life of a Legend

Smalls’ life is exemplary of daring achievement. The kind of achievement that can only result from perseverance. Though Smalls’ story could have concluded with his escape, he continued down an extraordinary path. He did not fade into the annals of history. Instead, he used his celebrity to fuel a life of action. There is no question as to whether or not Smalls seized the day consistently throughout his life.

Despite obstacles in his political career, Seatown observer Laura Towne described Smalls as “very cheerful.” Accounts of Smalls’ cheerful disposition are only overshadowed by stories of his cool head under pressure.

Though Smalls’ life has never received the widespread recognition it deserves, his legend lives on. In 2007, the US Army named a transport vessel (USAV Maj. General Robert Smalls) for Smalls, being the first Army ship named after an African American. In 2017, author Cate Lineberry wrote Be Free or Die: The Amazing Story of Robert Smalls Escape from Slavery to Union Hero chronicling Smalls’ life and reintroducing his story to the current generation.

Though Smalls had every reason to be vindictive, he never appeared to let his circumstances dictate his perspective. A heavily stacked deck often confronted him, yet he found a way to succeed.

Like the Planter sailing toward the Union blockade, Smalls courageously moved forward until the end.

If you enjoyed this article, please recommend it and check out my blog at

Originally published at

Featured image courtesy of the Library of Congress. Obtained via Robert Smalls image courtesy of Robert Smalls House courtesy of Planter image courtesy of the US Naval History and Heritage Command photo # NH 74054, courtesy of E.D. Sloan, Jr., 1971. Obtained via

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Buck Stewart

Written by

I run The Road of Trials, a publication dedicated to inspiring action and providing hard-won strategies for achievement, mental fortitude, and leadership.

The Road of Trials

Inspiration, Mindset, Achievement, Leadership

Buck Stewart

Written by

I run The Road of Trials, a publication dedicated to inspiring action and providing hard-won strategies for achievement, mental fortitude, and leadership.

The Road of Trials

Inspiration, Mindset, Achievement, Leadership

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