Under the Bloody Flag

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by John C Appleby


  From the outset, the war with Spain met with an enthusiastic response. For self-appointed anti-Spanish crusaders, who had been engaged in surreptitious hostilities for more than a decade, it was long overdue. Among the pirate fraternity, an unruly but potentially valuable resource of experienced and aggressive seafarers, it provided an appealing opportunity for redemption and service in a public cause. In June 1585 Sir George Carey, the governor of the Isle of Wight, informed Walsingham:

  that one Flood, a valiant and skilful pirate, weary as he protesteth of his former trade, vowing to lead a new and better life, seeketh to come in upon my word, and maketh offer of his service to be employed upon all the coast of Spain to discover what is in action or intended against us, only craving to be victualled, and if therefore he shall be found to deserve his pardon, then to have it.4

  The appeal of a better life, linked with popular patriotism and animated by deep-seated hostility towards Spain, may have spread widely among the seafaring community, especially in ports and regions where the loss of the Iberian trades was a serious threat to employment. The Spanish war thus benefited from a broad constituency of support within English society which was mobilized by the interplay between plunder and overseas expansion, Protestantism and national identity, combined with service for the Queen. The result was the creation of an impressive host of voluntary vessels, sent forth by promoters and adventurers of varied backgrounds, who were prepared to bear the risks of war either independently or in partnership with the Crown.

  The first real test of this approach to the maritime war was Drake’s raid on the Caribbean during 1585 and 1586. This was an impressive demonstration of English sea power, driven by predatory motives and informed by previous piratical enterprise in the region. It was also a state-sponsored expedition, the largest of its kind so far to challenge Spain across the Atlantic. Although no written instructions appear to survive, Drake’s purpose was to plunder the Spanish silver fleet while raiding settlements in the Caribbean, including Panama, possibly with the intention of establishing an advance base for continued depredation. Given the timing of the expedition, Drake probably planned to support or reinforce Ralegh’s recent settlement at Roanoke. In outline at least, this looks like an ambitious strategy for developing the Atlantic war, linking plunder with American colonization in a manner that played on religious and political rivalries. It may have included plans for the destruction of the Iberian fishery off Newfoundland, which was raided by Captain Bernard Drake during 1585. As envisaged by Richard Hakluyt, the leading propagandist of westward enterprise during the 1580s, Spanish and Catholic tyranny would be overthrown by a combined force of English Protestant imperialists with the assistance of discontented natives and slaves. Although this flattering and self-serving image was never shared by the Queen, whose interest in the sea war was primarily pragmatic, to some extent it was influenced by Drake’s own experience in the Caribbean, including his relations with the cimaroons, which may have exaggerated the expectations of a group of adventurers who identified themselves as God’s warriors.5

  The promoters of the expedition represented a powerful alliance of naval and maritime interests who had long been in favour of aggressive action against Spain. Drake and Hawkins probably contributed eleven vessels to the venture, while most of the other shipping was provided by their associates or supporters at court, including Leicester and the Lord Admiral, and merchants in London and Plymouth. The Queen furnished two vessels, the Elizabeth Bonaventure of 600 tons, in which Drake sailed, and the Aid of 200 or 250 tons. In all, the promoters mobilized a force of twenty-five ships and eight pinnaces, manned with a complement of more than 2,000 sailors and soldiers. Under the leadership of Drake, the captains included Martin Frobisher, Thomas Fenner and Francis Knollys, who possessed extensive sea experience, and a group of kinsmen and loyal associates, including Thomas Drake, William Hawkins and Richard Hawkins. Christopher Carleill, the son-in-law of Walsingham, served as captain of the Tiger and was in command of the land forces. Also included among the company was Pedro, an Indian originally from the island of La Margarita, who had been with Drake for about twelve years and was to serve as an interpreter.

  Maintaining command of this large, amphibious expedition, while fulfilling the expectations of its promoters, presented Drake with unprecedented responsibility. Although he held councils with captains and officers, and maintained discipline through improvised courts to deal with offenders, as during the circumnavigation, he appears to have sailed in dread of the danger of sedition and faction among the company. At Cape Verde he became embroiled with Knollys in a dispute over the administration of an oath which threatened to turn into a re-run of the Doughty affair. The quarrel rumbled on, with Knollys facing a court martial, but it never reached a crisis point, possibly because of his connection to the Queen.6

  The expedition left Plymouth on 14 September 1585. Shortly thereafter the Tiger captured a French vessel returning from Newfoundland with a cargo of fish. Claiming the vessel as lawful prize, on the grounds that it was bound for Spain, the English shared out their catch of fish and used timber from the ship as a supply for firewood. A few days later the expedition reached Bayonne, where it was supplied with fresh water and provisions. During these uneasy but generally peaceful contacts Drake provided local officers with official justification for the voyage, offering them a choice between peace and war, in retaliation for Philip II’s embargo of English shipping earlier in the year. Drake made it clear that he was acting in the service of his sovereign; subsequently, he was to be enraged at being described by Spanish officials as a corsair. While the fleet lay at Bayonne, however, Drake’s company sacked a religious house. The iconoclasm grew more furious during the course of the voyage, reflecting the spread of popular Protestant radicalism among mariners, which encouraged the misuse, vandalism and destruction of churches. Off the coast of Portugal the fleet encountered about twenty sail of English men-of-war, from London, Bristol and Southampton, which had raided and burnt the port of Viana. From the Iberian coast the expedition sailed on to the Canary Islands and thence to the Cape Verde Islands, where the abandoned settlements of Santiago and Porto Praya were set on fire. As the fleet crossed the Atlantic, the company were afflicted by the outbreak of a deadly disease which accounted for several hundred casualties. The extent of the losses may have had a crucial bearing on the subsequent course of the expedition, and in dissuading Drake from leaving a small occupying force in the Caribbean.7

  Following a brief stay on the unsettled island of Dominica, at the end of December the expedition arrived off Santo Domingo, once one of the most important settlements in the Spanish Caribbean, now in decline. The English encountered little resistance. During an occupation that lasted one month, they systematically looted and burnt the city. As churches were vandalised and destroyed, some of Drake’s men argued with the Spanish over matters of theology. The destruction only came to a halt when the defenders agreed to pay a ransom of 25,000 ducats, although the amount was a disappointment to Drake and his captains who had expected much more. In addition to the ransom, the English departed with an assortment of plunder, including church bells, ordnance, hides and three ships, which were exchanged for two old vessels out of the fleet, as well as eighty slaves, Turks, Frenchmen, Greeks and Africans.8

  This devastating assault on Santo Domingo was followed by an equally damaging raid on Cartagena, which Drake may have considered holding as an outpost for future use. According to one report, the English fleet arrived ‘flying black banners and streamers and menacing war to the death’.9 Although the Spanish were forewarned, after a confused clash along the sea shore, during which the English sustained casualties, the defenders reportedly fled like sheep. The capture of Cartagena strengthened a view among some of the English that God fought for them, overwhelming their enemy with blindness and fear. Most of the inhabitants escaped to a safe retreat in the interior; the fort was abandoned and two galleys were set on fire. The English stayed at Cartagena for m
ore than five weeks, burning the town as negotiations proceeded for its ransom. Though amounting to 107,000 ducats, again the amount was less than Drake anticipated. As at Santo Domingo the attackers ransacked the town of ordnance, church bells and anything else made of metal, while slaves of varied backgrounds were freed. By the time the expedition departed, at the end of March 1586, the English had accumulated as many as 200 Turks and a large number of Africans, who may have been intended as unwitting reinforcements for Ralegh’s settlement at Roanoke.10

  Although the Spanish put up little resistance to the raiders, the English suffered heavy losses to sickness and disease during their occupation of Cartagena. According to one report the losses amounted to 100 men. Cumulatively the rate of attrition discouraged Drake from proceeding to attack Panama. In February 1586 a decision was made to return home. During the return voyage to England the expedition destroyed the Spanish outpost of San Agustín, along the coast of Florida, partly to protect Roanoke from possible attack. When Drake made contact with Ralegh’s settlers in June, however, it was apparent that they had experienced a difficult and discouraging year of hunger and increasing native hostility. Drake offered the settlers a small vessel to re-settle in a more favourable location in Chesapeake Bay, but it was lost during stormy weather. Although the colonists were offered a replacement, they abandoned Roanoke and returned with Drake to England. While the early Roanoke voyages suggested that plunder and plantation could be combined profitably, encouraging the re-establishment of a small settlement in 1587, Ralegh rapidly lost interest in colonization in favour of privateering.11

  Drake’s expedition was a striking, but mixed, success. It dramatically revealed the range and capability of English maritime power, exposing the weakness of the Spanish monarchy within a vulnerable region of its American empire. The trail of plunder, destruction and iconoclastic violence was a damaging blow to Spanish reputation. The surprising ease with which Santo Domingo and Cartagena were taken suggested that Spain’s colonial settlements were deeply disorganized and demoralized, although the prospect of more damaging activity was foreclosed by the spread of disease among the English. The seizure and sack of Cartagena provoked rumours among the Spanish that Drake was going to inform Philip II about the unpreparedness and weak defences of the region. With both settlements stripped of their ordnance, local officials warned Philip of their exposure to further attack. Thus Santo Domingo was reported to be unarmed and ‘defenceless against any corsair who may undertake to finish us off’.12 Spanish reports from the Caribbean indicate that the damage may have been as much psychological as physical. As such the expedition exposed the fragile integrity of an expanding Iberian monarchy, by exploiting or revealing rivalries between the Spanish and the Portuguese, and reviving concern about the possibility of an alliance between English raiders and discontented natives and slaves. Drake’s challenge to Spain, moreover, was accompanied by reports that he would be followed by Don Antonio in command of a large fleet.

  For Drake and his associates the expedition amounted to a resounding declaration of war against Spain which provided a model for future development. In effect this anticipated the merging of the pirate tradition with royal service, creating the conditions for private adventurers to organize an Atlantic campaign against the Spanish monarchy, in cooperation with the regime. Yet there were signs that this alliance was problematic and unstable, not least in the ambitious expectation that strategic goals could be accomplished while the war not only paid for itself, but also earned a profit for its supporters. Indeed the financial return from Drake’s expedition was a disappointment: the plunder, estimated to be worth £60,000, failed to provide its promoters with a profit. According to Spanish report, although Drake:

  had promised the Queen of England to fetch her a million as her share … he was disturbed to see how little profit he had so far obtained [at Cartagena]; and even all his captains and soldiers were aggrieved because he had promised them so much and they saw that their part would be small, and so all the gentlemen said that he would not again find any to go out with him from England.13

  When set against the heavy human losses, amounting to more than one-third of the expedition’s company, this cast a shadow over the ability of the English to sustain such a conflict against Spain over a prolonged period. In addition, the failure of North American colonization, partly as a result of the counter-attraction of maritime depredation, left the development of a transatlantic strategy in disarray. The confusion was compounded with the Queen’s reluctance to exploit the advantage against Spain. In the immediate aftermath of the expedition she claimed that Drake had ‘exceeded his instructions’.14 In these circumstances it appeared likely that the latter would continue hostilities in the service of Don Antonio, possibly with the assistance of the Dutch.

  Nonetheless, the expedition had far-reaching diplomatic and international implications, placing England at the head of the forces of international Protestantism which were arrayed against Spain. Its value as anti-Spanish propaganda was underlined by the publication of an edited account of the voyage by Walter Bigges, with Latin and French editions in 1588, followed by English and German versions during 1589. Dedicated to Robert Devereux, 2nd Earl of Essex, Bigges’ Summarie and True Discourse was intended to maintain morale at a critical time while promoting the cause of the war party, by demonstrating ‘what great victories a fewe English men have made upon great numbers of the Spaniardes, even at home in their owne countreyes’.15

  Drake’s celebrated raid on Cadiz during 1587 appeared to provide strong support for a forward campaign at sea, despite the Queen’s caution and misgivings. The raid, an amphibious expedition of royal and privately owned vessels, was meant as a pre-emptive strike against the Armada which was assembling in Spanish and Portuguese ports for the invasion of England. As a reprisal venture, partly promoted by private adventurers, it was also intended to provide its backers with a profit. While there was no apparent incompatibility between these strategic and financial goals, the underlying uncertainty over their priority was a source of tension which may have been reflected in divided leadership and rivalry between Drake and the Queen’s leading officer, Vice Admiral William Borough, which flared into open hostility during the voyage.

  Drake left Plymouth in April 1587 at the head of a fleet of twenty-three vessels. Of these, six were owned by the Queen and eight belonged to London merchants, including four from the Levant Company. Drake contributed three of his own vessels, while the Lord Admiral furnished another. Despite the Queen’s late and abortive attempt to stop it sailing, the fleet departed on a wave of high expectation. The company, Drake informed Walsingham, was united as ‘one body to stand for our gracious Queen and country against Antichrist and its members’.16

  An account by Robert Long, a volunteer with the expedition, provides a fascinating narrative of the voyage, which employs classical and biblical allusions to portray Drake as the champion of England against the enemies of the gospel. Such propaganda seems to represent Drake’s increasingly strident fundamental Protestantism, though it also concealed the innate flexibility and potentially hazardous nature of the enterprise. On leaving England the expedition sailed for the coasts of Spain and Portugal, where Drake acquired valuable information from two Dutch ships about the shipping and provisions which were being assembled in Cadiz. Three days later the English sailed into Cadiz harbour, sinking and burning about thirty vessels. Although the expedition encountered resistance, unexpectedly Spanish naval forces inflicted little damage on the fleet. Despite the dangerous and unfavourable location, the galleys of Spain were ineffective against a force of sailing vessels. Thereafter Drake sailed to Cape St Vincent, where he put ashore a company of 800 men who captured and set fire to local fortifications. Faced with little opposition at sea, the fleet cruised along the coast, anchoring unchallenged in sight of Lisbon, while taking prizes and laying waste to the coastal fisheries.17

  The raid on Cadiz was a tactical success, but it failed to provide Dr
ake with sufficient plunder to make the voyage profitable. Consequently, after sending sick members of the expedition home, he sailed for the Azores in search of richer prey. Within twenty or thirty leagues of the islands he captured a Portuguese carrack, the San Felipe, using tactics widely employed by pirates and corsairs. It was a profitable catch. The ship was laden with cloth, silks and spices, subsequently valued at £100,000; a casket of rich jewels was retained by Drake for the Queen. He also freed 400 Africans aboard the carrack, who were apparently intended as slaves in Portugal and Spain, providing them with a vessel ‘to goe whether they lyst’.18 The capture of the San Felipe deeply alarmed the Portuguese and Spanish. The latter were reportedly in despair at the threat to the Indies fleet. For Drake, however, the expedition had fulfilled its aims, and by the end of June 1587 he was back in Plymouth.

  The expedition was a provocative challenge to Philip II. It exposed serious weaknesses in Spanish sea defences in home waters, and revealed the vulnerability of Portuguese shipping returning from the East Indies. Among the Spanish, the shock and disbelief fed suspicions that Drake worked with a familiar, while English reports claimed that the action at Cadiz hastened the death of the Spanish High Admiral, the marques of Santa Cruz, the intended leader of the armada. At the same time the venture served to affirm the striking effectiveness of the English sea war, demonstrating the profitable and tactical benefits of rapid mobilization and action. For Drake in particular, it underlined the case for aggressive action against Spain, and in a way that defined the defence of the realm with the godly cause. During April he wrote several letters to supporters and friends in England about the raid on Cadiz and other recent events. One, addressed to Walsingham, contained news of the fleet that the King of Spain was assembling, ending with an urgent appeal to ‘prepare in England strongly, and most by sea. Stop him now, and stop him ever’.19 Another was addressed to John Foxe, the preacher and martyrologist, and appealed to the clergyman for his remembrance and spiritual support, so ‘that we may have continual peace in Israel’.

 

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