The real pirates of the Caribbean: your guide to Nassau's pirate republic

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Rogers’ reputation preceded him, and the circumstances that had led the British government to turn a blind eye to the crime wave emanating from their far-flung colonial outposts had changed. A cold wind was blowing across the renegade republic, unsettling the pirate flag that brazenly flew from the hill fort above the harbour.

Many of the most infamous figures of the day – a collective of pirate captains known as the Flying Gang, who had been bossing and bullying the Bahamas for over a decade – were preparing to accept the King's Pardon the new governor offered, rather than risk the likelihood of a grizzly death at the end of a short rope by staying on the wrong side of the law.

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But not Vane. A cruel character with a horrible history – supported by a crew that was even more rash and unrepentant than their captain – he wasn’t about to give up his lucrative life of crime without a fight.

Wrong-footed and hemmed in by Rogers’ sudden arrival, Vane bought time by demanding the right to dispose of his ill-gotten swag before promising to accept the terms of the pardon, but by nightfall he knew he was cornered. It was time to surrender or swashbuckle his way out of the situation.

When was the Nassau pirate republic established?

Initially established as an English outpost called Charles Town, the settlement around the main harbour on New Providence Island in the Bahamas was renamed Nassau in 1695, after being torched by the Spanish in a skirmish typical of the time, when competing colonial powers constantly fought over footholds in the New World. Sir Nicholas Trott was installed as governor, but the so-called city – the Bahamas’ capital – was thinly populated and ripe for attack, especially as Europe’s Nine Years’ War was spilling into the Americas.

One year later, renegade English sea-captain Henry Avery arrived, fresh from pulling off the biggest pirate raid in history. His ship, the Fancy, had attacked and plundered the Grand Mughal dhow, Ganj-i-Sawai, which was laden with vast amounts of treasure.

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Using a false name and posing as a slaver, Avery employed bribery and deception to convince Trott to allow him into harbour, where the presence of his crew more than doubled Nassau’s male population. Trott, who doubtless suspected he was entertaining pirates, calculated this might deter an attack from the French, who were at war with England and had recently overrun nearby Exuma.

The attack on the Ganj-i-Sawai had put the crown and English merchants under huge political pressure, however, and when Trott realised who his guest was, he squealed to the authorities – but not before giving Avery advance warning and allowing him to escape with his loot, never to be seen again.

The pirates were gone, but not for long. Nassau was again left dangerously exposed and unprotected, and Trott soon moved on as the settlement was repeatedly attacked by the Franco-Spanish fleets during the War of the Spanish Succession, which erupted in 1701. Eventually, Nassau was effectively abandoned by English authorities, which allowed the increasing number of privateers active in the area to move in.

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The Spanish succession war – sparked by the death of Charles II, last Habsburg king of Spain, who died childless – pitted the forces of the Holy Roman Empire (Austria, Prussia, Hanover), England and Scotland (joined in the Acts of Union in 1707), Portugal, the Dutch Republic and one faction of Spain against France and Spain (loyal to Philip, duc d’Anjou). The conflict was fought across Europe and the New World, and was bigger than anything seen before.

A tactic long employed by the English during wartime was to skimp on the cost of a maintaining a big, expensive navy by issuing ‘letters of marque’ to private captains, authorising them to attack any ships flying the flag of an enemy nation and to capture the cargo (on the understanding that they should send a percentage of profits back to the Crown). Possession of this piece of paper was the sole difference between being a privateer (a legal occupation, actively encouraged by Crown and government) and a pirate (a criminal act, punishable by death).

During the succession war, lots of letters of marque were issued, and attacks on ships flying Spanish and French flags as they sailed in American waters were highly encouraged. When Britain pulled out of the conflict these letters were suddenly worthless, and privateers faced a choice: give up their lucrative life of violence and robbery on the high seas, or carry on beyond the law and become full-time pirates. It wasn’t a hard decision.

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Most of these men – captains and crew – were lifelong mariners who’d served in the regular navy, and weren’t about to rush back. Conditions were appalling, with draconian rules and horrific punishments, years at sea with little reward and scant opportunity to meet women, lots of discomfort and danger, and a high probability of early death.

Until the 19th century, the Royal Navy regularly paid sailors’ wages up to two years late, and it was common practice to hold back six months’ pay simply to dissuade men from deserting or mutinying. And even when they were paid, mariners’ salaries remained unchanged for nearly 150 years, between 1653 and 1797.

By contrast, as privateers and subsequently pirates, they could typically expect a proper share of any spoils blagged from boats they helped to plunder, could play an active role in a surprisingly inclusive system, and enjoy plentiful shore time in places like Nassau with its taverns and women. The violence and high probability of dying young stayed the same – but at least they faced the risks on their own terms.

Which pirates sailed from Nassau?

Prominent among those who now found themselves sliding into a criminal career were captains Benjamin Hornigold and Henry Jennings, once rival privateers who quickly became lead players in the Republic of Pirates, mentoring some of the era’s most notorious characters.

Hornigold's first forays into piracy happened during the winter of 1713–14, off the coast of Nassau, where he used a sloop and a flotilla of periaguas (sailing canoes) to harass merchant ships attempting to pass New Providence. Within three years, he'd amassed a pirate fleet of five vessels (including a 30-gun sloop called the Ranger – the most powerful ship in the region) and commanded a combined crew of 350 men. Hornigold's second-in-charge was a big bloke called Edward Teach, who would become better known as Blackbeard.

Jennings – branded a pirate in 1715 after two illegal attacks on Spanish interests – relocated from Jamaica to Nassau, and formed an alliance with Hornigold.

Besides Blackbeard, the stellar cast of criminals that graduated through the crews of Hornigold and Jennings included Charles Vane, 'Black Sam’ Bellamy, Stede Bonnet and 'Calico Jack’ Rackham. Collectively, they were known as the Flying Gang, and their audacious misdeeds would come to define the golden age of piracy, giving rise to many of the legendary antics we now associate with fictional pirates from page, stage and screen.

Who was in the Flying Gang?

The lead characters active in the Republic of Pirates were collectively known as the Flying Gang. The society was run like a surprisingly tight ship, underpinned by the same code of principles employed by pirates while they were at sea. They included:

• Edward 'Blackbeard' Teach
• 'Calico Jack' Rackham
• Charles Vane
• Stede Bonnet
• Olivier Levasseur
• Benjamin Hornigold
• Henry Jennings
• 'Black Sam' Bellamy

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And not all of these tales are based on fantasy. The Republic of Pirates flew a skull and crossbones, and it was governed according to the Pirates' Code, which made it far more democratic and egalitarian than most so-called civil societies at the time.

Alarmed officials from neighbouring colonies, such as the Governor of Bermuda, claimed that over 1,000 pirates were operating out of Nassau at the republic’s height, dwarfing the settlement’s law-abiding population, which numbered just a few hundred. Some reports suggest the city supported an equal number of prostitutes, and the taverns were doing a roaring trade.

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Yet, by most accounts, this community of criminals was well organised and reasonably disciplined, with Jennings acting as ‘commodore’ and Blackbeard elected as 'magistrate' – a terrifying man to have in charge of law enforcement.

When did the pirate republic begin to decline?

Cracks in the cornerstones began to appear over the vexed issue of whether British ships should be attacked. Hornigold, wary of the consequences, was against plundering vessels flying the Union Jack, but his less-cautious crew disagreed, and in November 1716 he was overthrown and replaced by 'Black Sam' Bellamy.

According to the code, Hornigold was set adrift with men who remained loyal, while Bellamy went on to have a spectacular but short career as a pirate captain – capped by the plunder of a British slaving ship, the Whydah Gally, loaded with gold and silver, having just offloaded its human cargo – before being drowned during a storm in 1717.

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Hornigold was proved right, however, and once their commercial interests began to be threatened, the British stopped ignoring the Republic of Pirates. They engaged the services of Woodes Rogers as a governor, dispatching him to clean up the colony and reign in the renegade captains.

Rogers roared across the Atlantic, bearing a proclamation from George I offering the King's Pardon to any pirate for crimes committed before 5 January 1718 – if they agreed to swear an oath and stop their illegal operations. Generous rewards were further given to those willing to turn pirate hunter, helping to bring in any members of their former fraternity who remained outside the law.

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This shrewd tactic fatally split the Flying Gang. Hornigold was one of several who accepted the pardon and went searching for the bounty on the heads of his former protégés. Jennings too sought and received a pardon under the amnesty, as did some 400 other pirates. But not Jennings’ underling Charles Vane, who jumped into the vacuum left behind by this pirate exodus, and seized command of Nassau – at least until Rogers arrived, surprising him into a dramatic course of action.

The fall of the pirates of the Caribbean

Blockaded into Nassau Harbour, Vane filled his formerly French flagship, the Lark, with gunpowder, set it aflame and directed it towards the navy vessels. As it exploded, Rogers' men quickly cut their anchor lines and took desperate evasive action, allowing the pirate captain and his cutthroat crew to escape in a swift six-gun sloop called the Ranger, firing a few volleys at the navy ships as they sailed out into open sea.

While most of his Flying Gang colleagues were now out of action, Vane kept raiding ships passing through the Bahamas and remained a thorn in Rogers’ side as he attempted to snuff out the remnants of the Republic of Pirates on Nassau and restore order.

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Even Blackbeard – who’d been rampaging along the coast of mainland America when Hornigold was deposed, committing crimes that made his reputation – had accepted the pardon and was living relatively peacefully in North Carolina.

Vane, who was being pursued by pirate hunters including Hornigold, tracked his old buddy down and tried to tempt him out of retirement, but only succeeded in drawing attention to the infamous pirate. Directly after Vane’s visit, Blackbeard was attacked and killed by a task force commissioned by the Governor of Virginia. Meanwhile, Vane’s crew had grown even more reckless than their captain. In November 1718, Vane was deposed by his quartermaster John ‘Calico Jack’ Rackham, who accused him of cowardice after he retreated from a fight with a large French man-o-war.

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Cut loose on a captured sloop, Vane was shipwrecked on the coast of Central America, before being picked up by a merchant ship. Unfortunately for the pirate, he was subsequently recognised and turned over to authorities in Jamaica, where he was hanged at Gallows Point, Port Royal, on 29 March 1720.

Calico Jack didn’t fare any better. Although he returned to Nassau in 1719 and pursued a pardon, while on the island Rackham began an affair with Anne Bonny, wife to one of Rogers’ sailors. Exposed, the pair pinched a sloop and embarked on a new pirate rampage – with another famous female, Mary Read, also in their crew – until they were cornered by a pirate hunter. Rackham too ended his days on the Port Royal gallows.

With Hornigold having turned pirate hunter, Jennings in retirement, and ‘Black Sam’ Bellamy, Blackbeard, Vane and Calico Jack all dead, the Flying Gang was decimated by 1721, and Woodes Rogers had succeeded in consigning the Republic of Pirates to history.

Woodes Rogers: the man who broke the Flying Gang

The man who brought down Nassau's pirate posse wasn't a newcomer to adventure. Woodes Rogers had conducted a privateering expedition with William Dampier in 1708–11, during which he had circumnavigated the globe while pursuing Spanish ships, and rescued the marooned sailor Alexander Selkirk – who'd spent four lonely years on Juan Fernandez Island, and subsequently inspired Daniel Defoe's Robinson Crusoe.

Rogers then set his sights on the Bahamas, striking a deal with King George I that he'd rid the islands of pirates, in return for a share of the colony's profits. By 1720, he'd successfully quashed the Republic of Pirates and restored New Providence's defences, but found himself imprisoned because of debts he'd wracked up in the process.

The subsequent publication of a wildly successful book, A General History of the Robberies and Murders of the Most Notorious Pyrates, (possibly authored by Defoe, under the pseudonym Captain Charles Johnson) made Rogers a national hero, prompting King George II to award him a generous pension and reappoint him as Governor. He died in Nassau in 1732.

Pat Kinsella is a freelance journalist specialising in history

This content first appeared in the May 2017 issue of BBC History Revealed