How a single straw hat helped a man steal a Confederate ship

Cultures · Published 11 October 2026 · Updated 25 October 2026 Swipe more like this →

In short: In the predawn hours of May 13, 1862, Robert Smalls performed the unimaginable. Using his intimate knowledge of Charleston Harbor, the enslaved wheelman commandeered a heavily armed Confederate steamer, navigating through deadly checkpoints to deliver seventeen people from slavery to freedom.

The escape was a masterpiece of calculated deception. At 2:00 a.m., while the white officers of the C.S.S. Planter were ashore, Smalls and a crew of enslaved men began their voyage. To evade detection, Smalls donned the wide-brim/immed straw hat of Captain C.J. Relyea, using the disguise to help mask his identity. He even ordered the crew to hoist Confederate flags as decoys, successfully responding to the coded signals required at two checkpoints, including the heavily fortified Fort Sumter.

The stakes were absolute. Equipped with roughly 200 ammunition rounds, the Planter functioned as a premium coastal vessel, featuring both a 24-pound howitzer and a 32-pound pivot gun. The crew was prepared to sink the vessel rather than be captured. After navigating through five checkpoints, Smalls reached the open sea, where he signaled the Union blockade by raising a white bedsheet, surrendering the ship to the USS Onward.

The impact of this feat resonated far beyond the harbor. The intelligence gathered from the ship's documents—including mine locations and shipping routes—was invaluable to the Union. Smalls's heroism became a national phenomenon, helping to persuade President Abraham Lincoln to authorize the service of Black soldiers in the Union Army. Following the war, Smalls transitioned from a Union Navy captain to a prominent statesman, serving five terms in the U.S. House of Representatives.

General information, not professional advice. Spotted an error? Flag the card or see corrections and complaints.

Intellect Plus is a visual educational discovery platform for exploring fascinating facts and ideas. Brain Food, Not Brain Rot. What is Intellect Plus?

Related

• How an enslaved man commandeered a Confederate ship to claim his freedom
• A stolen steamer became a blueprint for American naval heroism
• The Confederate ship that fired the Civil War's final shots in the Arctic
• The Confederate commerce raider that used a legal loophole to haunt the oceans
• The 34-hour bombardment that ignited the American Civil War from a harbor fortress
• Is the Roberts Court actually the least activist Supreme Court in American history?
• The frontiersman who pioneered asymmetric warfare and survived total financial ruin
• The legendary roc was a giant bird capable of carrying off full-grown elephants.
• From Cabinet Secretary to Substack Star: The Enduring Influence of Robert Reich
• From hip-hop label to global empire: How Jay-Z built the modern entertainment conglomerate
• How a former Jesuit trainee became Canada's most beloved and stolen children's author
• How a suburban identity crisis birthed the city of Rochester Hills, Michigan

More in US culture · More in Cultures · Latest · A–Z · All topics