Chapter 4.2 – The Buccaneers

According to historian Clarence Henry Haring (1885–1960), “The Spanish ships of the 16th and 17th centuries were notoriously clumsy and unseaworthy.”  Their towering poop decks and forecastles have been likened to “mansions that had gone a-sailing.” Combined with their short keels, this caused them to respond slowly to the tiller and made them easy prey to the swifter sloops and barques of the buccaneers. Besides, Haring notes:

Although the king expressly prohibited the loading of merchandise on the galleons except on the king’s account, this rule was often broken for the private profit of the captain, the sailors, and even of the general. The men-of-war, indeed, were sometimes so embarrassed with goods and passengers that it was scarcely possible to defend them when attacked. The galleon which bore the general’s flag had often as many as 700 souls, crew, marines and passengers, on board, and the same number were crowded upon those carrying the vice-admiral and the pilot. Shipmasters frequently hired guns, anchors, cables, and stores to make up the required equipment, and men to fill up the muster-rolls, against the time when the visitadors came on board to make their official inspection, getting rid of the stores and men immediately afterward. Merchant ships were armed with such feeble crews, owing to the excessive crowding, that it was all they could do to withstand the least spell of bad weather, let alone outmaneuver a swift-sailing buccaneer.

As the buccaneers closed on the target ship, they loaded their muskets and their best marksmen—excused from rowing so their arms would be rested and their hands would be steady—took up positions in the bows. From there they picked off the helmsman and any officers on which they could draw a bead and fired at any gun-ports which happened to be open. If a buccaneer noticed the prey attempt to yaw so as to train her guns on their boats, he called out so the helmsman could adjust the tiller to keep the masts of the quarry in a line, and so approach from astern.

An Attack on a Galleon | Howard Pyle

Coming up to the stern of their prey, they jammed her rudder with wooden chocks, then swarmed up her side and attacked her crew with cutlasses, knives and pistols—the first man to get aboard receiving an extra portion of the spoils.

After taking the prize, the buccaneers rounded up the crew and passengers, questioned them, and robbed all of their valuables. They frequently stripped the captives and stole their clothes—each buccaneer had the right to take a full change of clothes from each prize captured. They ransacked the ship and inspected the cargo to assess its value. The ship itself was also assessed, with an eye to using her as a cruiser.

Dividing the Treasure

As a rule, the buccaneers put their prisoners ashore at the earliest opportunity but held some until they could sell them as slaves. If the ship were old, leaky or otherwise valueless, they either stripped her of her guns and turned her adrift with her crew, or ran her ashore in a remote cove, where she could be burnt and her ironwork salvaged. 

The prizes they took usually contained a valuable cargo, for the buccaneers who had turned to sea-raiding were skilled at recognizing different types of merchantmen, or sometimes they had insider information to go by. They sailed these prizes to a Dutch, French or English port, where they sold her cargo—usually at a fraction of its real value. Then, as they had done when they were cow-killers, they’d carouse and engage in all manner of debauchery. Later, after their money had run out, they’d go back to sea.

If a prize was sound, swift and with a shallow draft—they preferred to sail in small ships—the buccaneers kept her as a new or additional cruiser.  Once they had removed her cargo, they sponged and loaded her guns, adding more cannon where they could and making other necessary repairs. Then, after loading new provisions, the sea-raiders laid their mats on her deck, secured their boats astern and embarked in search of new plunder.

A buccaneer ship’s captain was elected by his followers and had little control over them except in times of action. During those occasions, his word was law. Some leaders were former soldiers with a respected knowledge of warfare, and others were skilled navigators. Some, however, were simply known as lucky leaders. During a cruise, the captain had the same single vote as any other man on board. The men were poorly disciplined on board their ships and did only work that had to be done. They did little else that did not please them. No cruise came to an end until a majority of the company declared themselves satisfied with the amount of plunder taken. The decision, like all other important ones, was debated at the mast and decided by a vote.

During night watches, while some slept, some sang songs, danced on the open deck, fired guns and drank to the health of their comrades. Others gambled at cards and dice day and night, which nearly always led to quarrels and fights. To stop the gaming, a captain needed the support of the majority of his crew. Otherwise, his men could simply outvote him. Sometimes a few lucky gamblers would win all the plunder from a cruise, and the majority would call for a re-division of the spoil. Those who had differences that they could not settle peacefully were allowed to go ashore at the first opportunity, where they settled their differences with duels. 

Augmented by captured Spanish vessels, the buccaneer fleet grew in size. Frequently, they sailed as privateers under letters-of-marque: official commissions from various European nations with interests in the Caribbean. Such commissions provided the Brethren of the Coast with the legal right to take prizes on a similar basis as the national navies of the countries they represented. However, these were resourceful and audacious men, and they stretched the terms of their commissions to the legal limit—and sometimes beyond. By 1665, the Brethren of the Coast had grown to the size of a national navy. About 1,500 French flibustiers used Tortuga as their base. There they were given protection by the governor who issued letters-of-marque against the Spanish. Many took wives who they imported and settled down in the small colony. Some became planters in the western parts of Hispaniola that we know as Haiti.

In the late 1650s, the English buccaneers, at the urging of the governor of Jamaica, chose Cagway (renamed Port Royal in 1660) as their main base. And by the time England had consolidated its foothold on that island, the buccaneers were loosely integrated into its military and naval forces. Moreover, due primarily to the exploits of the Brethren of the Coast and the plunder they brought back to the city, Port Royal earned the reputation as the wickedest town in the world. Between 1665 and 1675—which included Harry Morgan’s heyday as admiral of the fleet—Port Royal may also have been the richest town of its size. 

The buccaneers maintained an uneasy alliance with the Caribbean colonies, for they needed a place to dispose of their plunder and obtain supplies. The colonist, for their part, needed protection from their Spanish neighbours. Besides, they benefitted economically from the rock-bottom prices they paid for Spanish loot and the sky-high prices they charged the carousing buccaneers. 

Even as their numbers swelled, buccaneers cruised mainly in separate companies, usually of less than 100 members. From their base at The Point at Port Royal, they raided Spanish settlements and captured Spanish ships. Individual leaders included Bartholomew Portugues, Roche Brasiliano, Lewis Scott, John Davis, Richard Guy, Sir Thomas Whetstone (a cousin of Cromwell), John Morris, David Martien, Jacob Jackman, Thomas Freeman and dozens more. Eventually, the buccaneers banded together to form a powerful fleet capable of taking on even the heaviest fortified settlements and cities. Their first “admiral” was a Dutchman named Edward Mansvelt, known to the English as Edward Mansfield. Harry Morgan became his successor.

The buccaneer era spanned a period in the 17th century from some date before 1630 to the signing of the Treaty of Ryswick in 1697. They came later than—and should not be classified with—the Elizabethans: Drake, Hawkins, Raleigh, Gilbert, Grenville and Frobisher. Nor should they to be included in the Pirate Era that succeeded them, for men like John Rackham, Edward Teach (Blackbeard), and Bartholomew Roberts (Black Bart) were simple sea robbers who were not acting under legal government commissions.