Stranger Than Fiction

March 2026

Pirates of Bermuda: Civil War Blockade Runners and the Seizure of the S.S. Roanoke
by Dean Jobb

The singing was coming from S.S. Roanoke’s stern, where some of the mail steamer’s passengers had gathered to pass the time. The ship’s dual side-mounted paddlewheels were making music of their own as they devoured the inky water like a voracious beast. It was just after nine o’clock on one of the last nights of September, 1864 and about a dozen shadowy figures—men who had boarded just before the New York-bound ship left Havana—were roaming the deck.

Among the latecomers was a bearded man with a wisp of moustache and an unruly head of hair. A fellow passenger was startled to discover the man had changed his clothes since coming aboard. He now wore the steel-grayuniform of a Confederate naval officer.

“In the name of the Confederate States of America,” Lieutenant John Clibbon Braine shouted over the thrashing of the paddlewheels and the voices of the singers, “I demand the surrender of this vessel as a lawful prize.”

Seizing the 220-foot steamer and rounding up its crew took almost an hour. Pistol shots were fired to ensure everyone on board realized that Braine and his men meant business. Roanoke’s captain, Francis Drew, was cornered in his cabin and surrendered. The ship’s carpenter grabbed an axe and took a swing at one of the assailants. He died in a volley of bullets and his body was dumped overboard. A stray shot wounded an assistant engineer in the arm. The officers and crewmen were manacled and raiders who knew how to handle a ship took control as passengers were herded below deck.

Braine set a new course. When the steamer passed the southern tip of Florida it veered eastward, away from New York and into the Atlantic. His destination was a cluster of islands more than a thousand miles northeast of Cuba. While this outpost was under British rule, it was a hotbed of Civil War intrigue and a refuge for the sleek, swift Confederate ships that broke through the Union Navy’s blockade of Southern ports to deliver guns, ammunition, and other crucial supplies. Roanoke and its twin 260-horsepower engines would be a welcome addition to the fleet of Rebel blockade runners based in Bermuda.

“Bermuda,” local merchant John Tory Bourne noted in 1862, “is a half-way house for commerce between the Confederate States of America and the Mother Country.” Britain remained neutral during the Civil War but its colonial ports were open to merchant ships, and Bermuda became the South’s middleman and lifeline. The islands, with a population of just over 11,000, were less than 700 miles from Wilmington, North Carolina, a port that became the main destination for blockade runners. Ships from Britain and Europe, laden with munitions and essentials such as food and blankets, docked in Bermuda to transfer their cargoes to faster, Confederate-flagged steamers built for running the blockade. Most made it through the thin line of Union warships trying to seal off 3,500 miles of coastline—as many as nine out of ten evaded capture or sinking in the early years of the war—and returned with bales of cotton, the South’s main export. The cotton was unloaded for reshipment to textile mills in Britain, earning the Confederacy the revenue needed to fight the war. At one point in 1862, 80,000 guns and 100 tons of gunpowder were in Bermuda warehouses, ready for the run to Wilmington.

Sixty percent of Bermuda’s population was Black (enslavement, the scourge that ignited the war, had been outlawed in the British Empire three decades earlier) but prewar commercial and social ties meant local sentiment was solidly pro-South. “We have ever regarded the Federals’ (Union’s) cause as hopeless and wrong,” Bermuda’s Royal Gazette noted in 1863. “The Confederates have as much right to self-government as we have.” While Southern agents and ships’ crews were welcomed on the islands, United States consul Charles Allen faced death threats and was accosted on the street; the flagpole outside his office was chopped down to prevent him from flying the Stars and Stripes.

“Every hole and corner,” he griped, “is filled up with Southerners.”

Bermuda was a major North American station for the Royal Navy, which was based in a heavily fortified dockyard at the western tip of the islands. The town of St. George, at the opposite end of the territory, boasted a large, sheltered harbor and became the base for Southern commerce and the blockade runners. “The Harbor is so full of vessels there is scarcely a chance for one to anchor—all secessionist,” Allen noted in a report to his superiors in Washington. Major Norman Walker, a Confederate officer, was dispatched to St. George as the Rebel government’s Bermuda purchasing agent and took rooms in a boarding house on the town’s main square, just steps from the busy waterfront.

St. George became a wartime boomtown. Local merchants grew rich and one enterprising businessman set up a dock where ships could unload, load, and take on coal at the same time, minimizing the downtime between runs of the blockade. Sailors and dockworkers were well paid and there were plenty of tavernkeepers and brothel madams eager to take their money. The streets were filled with “dissipated dirty sailors,” a Royal Navy surgeon noted with disgust, “more or less intoxicated and always in a state of perpetual debauch.” Brawls were common and there were tense encounters between Black stevedores and the white Southerners—“reckless, roaring, devil-may-care fellows,” as one local described them—who crewed the blockade runners.

On the afternoon of October 4, 1864, Lt. Braine and his Confederate pirates anchored S.S. Roanoke just outside St. George’s harbor as they plotted their next move.

Braine is a chameleonlike character in Civil War history—part pirate, part con man, and an all-in supporter of the Confederate cause. He claimed to be an Englishman but, by one account, hailed from Missouri, a hotly contested and war-torn border state. Braine’s Rebel sympathies had landed him a stint in a Union prison but by 1863 he was in the British colony of New Brunswick, which bordered on Maine, selling subscriptions to a fictitious business directory. He used the proceeds to finance his first ship-stealing scheme.

In December 1863, Braine and a band of Confederates and Southern sympathizers posed as passengers and boarded S.S. Chesapeake, which shuttled between New York City and Portland, Maine. Soon after leaving New York, they retrieved pistols and handcuffs hidden in their luggage and commandeered the steamer. A startled passenger, awakened by gunshots, asked a passing crewman what was happening.

They were now “prisoners to the Confederates,” she was told.

One crewman was shot dead in the melee and two others were wounded. Braine’s plan was to use the ship as a blockade runner, but he needed to take on more coal for an extended cruise. Union gunboats were soon in pursuit and cornered the pirates as they tried to refuel near Halifax, the capital of the neighboring colony of Nova Scotia and, like St. George, a hub for blockade running. Braine and most of his men escaped, but one, who hailed from New Brunswick, was captured. The seizure of the ship in British waters and the arrest of a British subject created a diplomatic furor that inflamed tensions between the Union and Britain.

When Braine followed the same gameplan to commandeer Roanoke almost a year later, he also faced the same problem—he needed to replenish the ship’s coal bunkers. The Bermuda authorities, however, refused to allow a vessel seized as a war prize to enter St. George’s harbor or to be furnished with supplies. Braine rowed ashore, hoping to have fuel and provisions smuggled to the ship under cover of darkness, but few Bermudians were willing to break the law to help him. After four days and nights spent hovering near the harbor’s mouth, the ninety-five passengers and crew were transferred to passing ships. Braine’s men scuttled the steamer, setting it on fire before casting off in longboats. They likely helped themselves to the $17,000 in U.S. currency and $4,000 in gold that had been among the ship’s cargo. Roanoke appears to have sunk near a spot known as Five Fathom Hole.

When Braine and his raiders made landfall, they were arrested and imprisoned in St. George. They were charged with piracy, but when local magistrates assembled to hear evidence Braine produced a commission from the Confederate Secretary of the Navy, issued in May 1864, authorizing him “to capture upon the high seas” the Roanoke or another steamer on the New York-to-Havana route and to deliver the ship to a Confederate port. If the document was genuine, they were not murderous pirates—they were combatants who had carried out the orders of their superiors. A lawyer acting for Bermuda’s attorney general, no doubt bowing to local sympathy for the Southern case, withdrew the piracy charge. Braine and his men were set free. No one was prosecuted for the murder of the ship’s carpenter, an innocent man caught in the crossfire as Braine exercised his right to wage war on the Union.

A newspaper in Richmond, Virgina, the Confederate capital, cheered the decision to dismiss the “untenable” allegations. The Northern press, understandably, was outraged. The Philadelphia Inquirer described the court proceedings as “a complete farce” and denounced the Bermuda authorities for allowing Braine’s commission, which could have been a forgery, to absolve him of his crimes. The New York Times viewed the affair as proof the Confederates, who were losing the war on the battlefield, were becoming desperate. Roanoke’s seizure was a stunt “intended to catch the eye and tickle the fancy of foreign sympathizers” and revealed that the Rebels only had “strength enough left to be mischievous.”

Bermuda’s days as a Confederate base were numbered. By 1865, blockade runners stood only a fifty-fifty chance of making it past the ever-tightening cordon of Union warships. The final blow came early that year when Wilmington, the Confederacy’s last major seaport, was captured. Charles Allen, Bermuda’s beleaguered U.S. consul, was jubilant. “The blockade runners & their aides feel their doom is settled,” he reported. “Had they known that the islands were to sink in twenty minutes, there could hardly have been greater consternation.” St. George’s harbor emptied and merchants auctioned off stockpiled goods once bound for the South. Sailors and stevedores drifted off to other ports in search of work.

Braine commandeered or destroyed more Union ships before the war ended. Arrested in New York in 1866 for his piracies, he spent three years behind bars awaiting trial before the charges were dismissed. News reports described him as “the last Confederate prisoner of war.” After his release, Braine embarked on a lecture tour to boast of his wartime exploits and resumed his swindling career. He was jailed for fraud in Baltimore in 1903 and died three years later in Alabama. “Of such people,” Civil War historian Robin Winks noted, “are historical novels made.”

Dean Jobb’s latest book A Gentleman and a Thief: The Daring Jewel Heists of a Jazz Age Rogue (Algonquin Books and HarperCollins Canada) tells the incredible true story of Arthur Barry, who charmed the elite of 1920s New York while planning some of the most brazen jewel thefts in history. It’s a New York Times Editors’ Choice and a Canadian bestseller. Find him at deanjobb.com.