Under the Bloody Flag

by John C Appleby

  Despite these successes, Scottish complaints against English piracy continued. Scottish vessels were spoiled, and their companies ill-treated, along the east coast. In August 1574 Killigrew warned that pirates were ‘so openly maintained’ by the inhabitants of Berwick ‘that it makes evil blood among them’ in Edinburgh.40 Later in the year the council faced further complaints against groups of rovers, led by Captains Hill and Hudson, who were bringing plundered wheat, rye and other commodities into the border town.

  As this record demonstrates, the crisis at sea during the late 1560s and early 1570s was expressed in varied forms of depredation. Within the Channel the distinction between piracy and privateering was profoundly confused. In April 1574, according to report, the sea was so crowded with rovers and men-of-war that ‘no ship will escape them, unless a remedy be devised’.41 But the escalation in maritime violence and plunder, in part the result of wider political and religious divisions, was heavily focused on Spain. In England the lawlessness at sea served as a lightning rod for anti-Spanish enterprise, particularly among adventurers whose interests and ambitions were drawn westward. Within Spain there was mounting concern that the disorder and depredation threatened its Atlantic interests. Against a background of swirling rumours regarding the intentions of the Dutch and French privateering fleets, reports from London suggested that groups of adventurers, including Sir Richard Grenville, reputedly a ‘great pirate’, were involved in aggressive schemes for transatlantic raiding.42 What made such reports so alarming was their appearance at a time when English piracy, under the leadership of Drake, had exposed serious weaknesses in an acutely vulnerable region of the Spanish Caribbean.

  The pirate invasion of the Caribbean during the 1570s

  The spread of piracy into the Caribbean during the 1570s was an ambitious expansion of English depredation. Superficially it was provoked by the clash at San Juan de Ulua in 1568, but its origins lay deeper in the troubled history of Anglo-Spanish relations which can be traced back to the 1540s. It was also related to the vulnerability of Spanish trade and settlements in the Caribbean, which French privateers and pirates were the first to exploit. As Drake’s voyages indicate, the success of the English initially depended on cooperation with the French, as well as on the support of the cimaroons, runaway African slaves who had established autonomous communities beyond the jurisdiction of Spanish colonial authority. Their alliance with Drake had profound implications, though essentially it was based on a shared hostility towards the Spanish. In these circumstances English predatory incursions into the Caribbean initiated a small-scale, unofficial war for the riches of Spain’s empire in America. Under the resourceful leadership of Drake, who adapted the tactics of pirates and rovers across the Atlantic, initially it met with surprising success in terms of plunder and profit, creating the conditions for a more sustained assault on the region.43

  The outburst of marauding in the Caribbean by the English, between 1570 and 1574, involved at least ten separate ventures, about half of which were organized by Hawkins and his associates. Thereafter the number declined. From 1574 until the outbreak of the Anglo-Spanish war in 1585 evidence survives for four ventures.44 The inability of English adventurers to capitalize on the success of Drake during the early 1570s reveals the difficulties in sustaining a transatlantic campaign of plunder under unfavourable political conditions. Yet this was an experimental phase of trial and error when English rovers opportunistically probed for areas of weakness, while acquiring the confidence and experience to survive in a new and hazardous environment.

  Drake was in the forefront of English raiding in the Caribbean, though it was his later reputation which lent the expeditions of the early 1570s their allure. His self-image also demanded that these voyages were presented as legitimate revenge and reprisal. There is little doubt that he would have strenuously denied any accusation of piracy, despite his lack of a covering commission. His three voyages into the Caribbean during these years have the appearance of small, speculative ventures which at first may have combined trading with raiding. They occurred at a time when the number of French and Dutch pirates or privateers was increasing. Among the Dutch, rovers from Flushing claimed to be the subjects of the Prince of Orange, operating under his command. Spanish reports suggest that English activity was initially overshadowed by other Europeans. Although the English soon came to play a prominent role in Caribbean plunder, it was probably based on close coordination with Huguenot raiders.45

  In the aftermath of Hawkins’ last slaving voyage, Drake was involved in two poorly recorded voyages to the Caribbean, in 1569 and 1571. In the first he sailed with two small ships owned by William Hawkins, possibly with the intention of combining trade and plunder. During 1571 he appears to have sailed as part of a small fleet of three vessels sent out by John Hawkins in partnership with William Winter and his brother, George. Drake was in command of the Swan of 25 tons, the company of which included Richard Dennys, a merchant of Exeter who was also one of the promoters of the venture. In consortship with a group of French rovers, and with the aid of an African guide, Drake raided the region around Rio Chagres near the Panama isthmus, an exposed and defenceless part of the Spanish Caribbean that was already a favourite haunt for pirates. He returned with a substantial haul of booty, raising ambitious expectations among his supporters for the success of another voyage.46

  Drake’s third and last expedition in this sequence amply fulfilled these expectations, but the outcome of the voyage lay in the balance until he gained the assistance of the cimaroons, and was reinforced by French adventurers led by Guillaume le Testu. Drake set out from Plymouth in May 1572 with two vessels, the Pascha of 70 tons and the Swan of 25 tons, and a company of seventy-three men and boys, including his brothers, John and Joseph. The Pascha also carried three pinnaces, ready to be assembled across the Atlantic, for use along coasts and rivers. Returning to familiar territory, Drake and his men constructed a fort at Port Pheasant, a secure harbour with good resources of fish and game. Though intended as a temporary base for raiding, it was the first English habitation in America; it included thatched buildings and a small shipyard.47

  The arrival of James Ranse with a company of thirty men, in a vessel owned by Sir Edward Horsey, captain of the Isle of Wight, strengthened the English presence in the region. Led by Drake, a combined force attacked Nombre de Dios in a pre-dawn raid, but it was misjudged and based on poor intelligence. Although Drake tried to rally his discontented men, claiming to have ‘brought them to the mouth of the treasure of the world’, the attack was abandoned with one fatality and many wounded.48 A Portuguese account by Lopez Vaz, subsequently published by Richard Hakluyt, presented an unflattering portrait of fearful English pirates who fled in the face of limited Spanish resistance, abandoning their equipment and stripping off their hose to escape aboard their pinnaces.

  Following Ranse’s departure after the failed raid on Nombre de Dios, Drake reconnoitred the coast of the Spanish Main as far as Cartagena, taking several small vessels. Ashore he kept his company busy with a schedule of work and recreation, which included the construction of a building for meetings, a visible projection of the cooperation, consent and community that deep-sea pirate leaders tried to promote. The English traded with the local Indians for provisions, from whom they received gifts of fruit and bows and arrows, as well as information regarding Spanish activity. Contact was established with the cimaroons, who indicated their willingness to aid Drake. According to the account of Vaz, it was the cimaroons who informed Drake of the mule trains which crossed from Panama to Nombre de Dios laden with silver and gold.

  But time appeared to be running out for the pirates. Later in the year they heard alarming reports that Spanish frigates, manned with Indians armed with poisoned arrows, had been sent to hunt them down. During November, moreover, the company was ravaged by sickness. Many died of fever within two or three days. The death toll was devastating. By the end of the year Drake’s company was reduced to about thirty men. Am
ong the fatalities were his brothers: one was killed in a skirmish with the Spanish, the other died from sickness.

  In these difficult circumstances, the support of the cimaroons became crucial. While providing Drake and his men with vital provisions and intelligence about the Spanish, they reinforced the depleted and demoralized company with experienced warriors and guides, who taught the English to live off the land. Without their assistance it is difficult to see how the raid across the isthmus could have gone ahead. During a visit to a cimaroon settlement Drake heard a detailed account of their conflict with the Spanish, who ‘they kil like beasts, as often as they take them in the woods’.49 News of one cimaroon leader, who was reportedly capable of sending out 1,700 fighting men, reinforced Drake’s determination to establish closer relations with these rebels against Spanish colonial authority. According to a later account of the expedition by Philip Nichols, a clergyman, published in 1628, which ‘was reviewed by … Drake … before his death’, this included attempts to convert the cimaroons to Protestantism. Although they lacked priests, evidently ‘they held the crosse in great reputation’. At Drake’s persuasion, ‘they were contented to leave their crosses, and to learne the Lords prayer, and to be instructed in some measure concerning Gods true worship’.50

  Even with the support of the cimaroons, the first attempt to seize the mule train failed. At this stage the English were reinforced by the arrival of le Testu with news of events in Europe, including the massacre of the Huguenots in France. The French agreed to join Drake and the cimaroons in another attack. It was spectacularly successful. The raiders seized as much gold as they could carry, though they were forced to bury the silver, most of which the Spanish later recovered. Spanish officials estimated their losses at more than 80,000 pesos in gold. Once the plunder had been divided Drake returned for England. Before leaving he exchanged gifts with the cimaroons, who appear to have expected him to return in the future. The expedition arrived back in Plymouth on Sunday 9 August 1573. After it entered the harbour, during ‘sermon-time’, the church emptied as the congregation flocked to ‘see the evidence of … our captains labour and successe’.51

  Drake’s raid on the isthmus was more than piracy or outlawry. The alliance with the French, acknowledged with an exchange of gifts, appeared to represent an extension of the predatory reach of international Protestantism which envisioned a godly war across the globe against the forces of Catholicism. At the same time the alliance with the cimaroons cast pirate leaders, and some former slavers, in the role of freedom fighters who were prepared to support rebellious slave communities in guerrilla warfare against Spain.

  For Spanish colonial officials the league between the English and the cimaroons was a shocking and dangerous development which provoked widespread alarm. According to one stark warning of May 1573, if Nombre de Dios was taken by the English, Panama would be ‘theirs as easily as the words are said’, because of the rumoured support of 2,000 cimaroons.52 If this happened, furthermore, ‘they have the means to settle along the Pacific and build ships outside Panama’. Among the Spanish, piracy was confused with the threat of English expansion. Officials urged Philip II to take action to prevent future raids and to forestall the possibility of pirate settlement, by stationing galleys along the coast. Against a background of prolonged French raiding, Drake’s incursion appeared to be part of a concerted campaign that threatened to drain Spanish America of its wealth. In November 1573 representatives from Nombre de Dios complained of the loss of gold and silver during the previous seven years, reputedly worth two million pesos, and of the deaths of more than three hundred people on land and at sea.53

  Despite these alarming reports, English pirates and rovers were unable to build on Drake’s success in 1573. Revealingly, Drake did not return to the Caribbean until 1586. Pirates continued to sail thence during the 1570s, but the successors of Drake met with mixed success. In 1574 a pirate group, led by John Noble, pillaged various vessels along the coast of Nombre de Dios. However, the pirates were captured and executed, except for two boys who were sentenced to servitude in the galleys for the rest of their lives. Early in January 1575 another group of rovers, led by Gilbert Horsley, joined forces with French corsairs in an expedition up the San Juan River, in Nicaragua, daringly seeking to sack weakly defended settlements in the interior. Though the Spanish were taken by surprise, the pirates retreated after encountering and spoiling several vessels sailing downstream to Veragua. Horsley and his company of twenty-five men, who included a Portuguese pilot, plundered the vulnerable coasting traffic, reportedly torturing various passengers either for money or information, though they withdrew to avoid clashing with stronger vessels.54

  There may have been a brief upsurge in pirate activity, both English and French, during 1576 and 1577. In March 1577 five pirate ships were cruising off Veragua, the smallest of which was manned with eighty men. By April the number had increased to sixteen sail, ‘all out with the intention to sack these cities of the Main, and cross to the Pacific’.55 But the English expeditions expose the underlying limitations of this early wave of Caribbean depredation, while indicating its appeal for leading members of the regime. During the summer of 1576 Andrew Barker, a merchant of Bristol who claimed to be seeking compensation for losses sustained in the Canary Islands, set forth with a small expedition, made up of the Ragged Staff and the Bear, the promoters of which included Leicester. It was a quarrelsome, mutinous and unsuccessful voyage. Barker captured a number of vessels off Trinidad and along the coast of the Main, allegedly throwing the crew of one ship overboard. The prizes included a ship laden with gold, silver and emeralds, valued at £500. Among the passengers was a friar who had an emerald, set in gold, hidden around his thigh. Growing discontent among Barker’s men exploded in mutiny off the island of La Guanaja. Barker and several others were forced ashore, where they were surprised and killed by the Spanish. Their heads and one hand were subsequently displayed as war trophies before the municipal authorities of Trujillo. The survivors went on to raid the neighbouring island of Ruatan, seizing several small vessels in which they set sail for England. The shipwreck of one of the vessels off Cuba persuaded the company to return to the Honduran coast, where several were captured and later executed by the Spanish. A number returned to Plymouth during 1578, and were arrested to stand trial as accessories to the death of Barker. According to Hakluyt’s account of the voyage, the ring leaders received lengthy prison sentences, while some of the others ‘shortly after came to miserable ends’.56

  The expedition led by John Oxenham, who was with Drake in 1572, was more ambitious in scope, though much less successful in outcome. Oxenham left England during April 1576 in command of a vessel of 100 tons and a company of fifty-seven men, with the intention of trading with the cimaroons for gold and silver. In reality this was a pirate voyage which drew on Drake’s earlier experience. Shortly after arriving in the Caribbean, Oxenham established contact with the cimaroons, who were keen to know ‘if captain Francis was among them’.57 Oxenham’s company spent the winter at the cimaroon settlement of Vallano, during which time they constructed a pinnace for raiding in the Pacific. The following year, in February 1577, with a company of about fifty men, which was reinforced by nine or ten cimaroon leaders, the English raided the Pearl Islands off Panama. The attack caught the Spanish completely by surprise, confirming the fears of colonial officials about the security of the coastal trade between Panama and Peru.

  Oxenham’s success at the Pearl Islands was striking, but short lived. Spanish reports indicate that the raiders carried off a substantial haul of plunder, including gold, silver and pearls, as well as seventy slaves who were handed over to the cimaroons. It was accompanied by a furious outbreak of iconoclastic violence, with the destruction of images and crucifixes, and the public assault and humiliation of a friar, who was forced to wear a chamber pot on his head. In another powerful example of symbolic violence, a Spanish colonist had an iron collar placed around his neck by one of the cimaroon
s. The raid on the Pearl Islands was followed by the seizure of a rich vessel laden with gold and other commodities off Guayaquil.58

  The Spanish responded by sending out expeditions to hunt down the pirates, while launching raids against cimaroon settlements. During the six months following the raid much of the booty was recovered. Oxenham’s company dispersed, suffering heavy casualties at the hands of the Spanish. The ferocity of this campaign appears to have weakened support for the English among the cimaroons. Oxenham later claimed that they blamed the English for their ruin, and consequently treated them badly. Spanish hostility was intensified by rumours of increasing pirate violence across the Main. This ‘new development’, according to one Spanish report, included the castration of two Franciscan friars.59 By October 1577 Oxenham and seven members of his company had been captured. More were rounded up later in the year, though a small group managed to escape, possibly returning to England. Oxenham and his principal officers were subsequently taken to Lima and executed in November 1580.

  For the Spanish, the spread of English raiding into the Pacific starkly demonstrated the dangers to colonial commerce and settlement from small-scale provincial adventurers, who seemed to be capable of promoting piratical ventures with little check from the regime. Oxenham informed the Spanish that ‘no licence or permission of anybody was necessary, for these and more can depart out of England without there being required more licence than their will to go’.60 However, Oxenham’s voyage came at a time when English depredation in the Caribbean was losing momentum. In part this was the result of the inherent dangers and difficulties of transatlantic plunder. These grew progressively worse as Spain improved its defence of the isthmus region, helped by the failure of the English alliance with the cimaroons to develop. At the same time an unfavourable political and diplomatic environment in England weakened support for a direct assault on Spain’s colonial possessions in America, though the Queen’s interest in more indirect and discrete activity was demonstrated by her support for Drake’s voyage of 1577. Furthermore, the seafaring infrastructure appeared to be ill-suited for sustained predatory venturing across the Atlantic, particularly as piracy and sea roving were flourishing in the seas around the British Isles. Most of the piratical ventures into the Caribbean during the 1570s were undertaken by small-scale, marginal operators from provincial bases in the south-west, who were unable or unwilling to bear the hazards of a dangerous and mercenary business.