Under the Bloody Flag

by John C Appleby

  Though launched with high expectation of placing Spain on the defensive, from the outset the expedition was weakened by tension between Drake and Hawkins, and by confusion between public and private interests. Both were evident in the emergence of rival forces and factions within the fleet, which cruelly exposed the limitations of ageing sea commanders. The awkward hesitancy of Hawkins and the brash overconfidence of Drake were exacerbated by their old and out-of-date intelligence of the Spanish Caribbean. But the conduct of the expedition also pointed to deeper weaknesses in the organization of the war at sea which, in the short term, strengthened a view that Caribbean enterprise was best left to ‘filtchinge men of warre’ rather than large, albeit hybrid, fleets.93

  Against the advice of Hawkins, outward bound the expedition visited the Canary Islands in search of fresh water and provisions. It was a brief, but ominous, diversion. Drake’s company sustained several casualties, while Spanish officials sent a vessel to the Caribbean warning of the arrival of the fleet. When the English reached the West Indies, the Spanish fleet despatched earlier in the year seized a straggling vessel, the Francis. Its company provided valuable information of Drake’s presence and of his intended destination.

  The attack on Puerto Rico did not go according to plan. While the English fleet approached in some confusion, the defenders sank several vessels in the mouth of the harbour to hinder their approach. The attackers inflicted some damage on the fort with their ordnance. However, a night-time attempt to destroy the Spanish ships went disastrously wrong when the raiders were illuminated by the light from their fireworks. After three days, during which the English sustained significant casualties, Drake withdrew. Among the dead was Hawkins. The Spanish claimed that he was killed in conflict, ‘shewinge divers signes & markes of him’, but the cause of death was a lingering sickness.94 Drake also had a lucky escape off Puerto Rico, when a stool on which he was seated, while drinking a pot of beer, was struck by a stray shot from the shore.

  Departing from Puerto Rico, Drake boasted that he would take the company to twenty places more profitable and easier to take. In December the expedition seized the town of Rio de la Hacha along the coast of the Main. Although abandoned, and lacking much in the way of booty, the English took many prisoners, including African slaves who voluntarily surrendered. While the town was ransomed for 24,000 pesos, Drake raided the neighbouring pearl fishery, capturing a vessel laden with wine and some money. As the fleet cruised along the coast, finding other settlements forewarned of its arrival, Drake avoided an attack on Cartagena in favour of sailing directly for the isthmus.95

  Landing at Nombre de Dios, the commanders decided on a rapid march to Panama in the hope of finding hidden treasure. But the march was abandoned in the face of unexpected resistance from the Spanish, mounting casualties and concern at spoiled and short supplies. According to Thomas Maynarde, a close associate of Drake, among the survivors the ordeal sapped morale and support for the expedition. Early in January 1596 Drake called a council of officers, at which it became painfully apparent to Maynarde and others that he was ‘at the furthest limit of his knowledge’.96 The council agreed to sail for Nicaragua. Before the fleet departed, the English set fire to Nombre de Dios, sinking fourteen small frigates and acquiring a modest amount of gold and silver.

  With Drake troubled in mind, the fleet anchored off an uninhabited island in search of fresh provisions. Only a few tortoises were taken. The toll of casualties mounted, as a result of the spread of disease and short rations. Sailing for Porto Belo, Drake could barely conceal his grief from Maynarde:

  protestinge … hee was as ignorant of the Indies as my sealfe and that hee never thought any place could be so changed … yet in the greatnes of his minde hee would in the end conclude with these words. It matters not man God hath many things in store for us, and I knowe many meanes to doe her majestie good service & to make us ritch, for wee must have gould before wee see Englande.97

  But the arrival of the fleet at Porto Belo was marked by the death of Drake. He was buried at sea in a lead coffin.

  Baskerville attempted to salvage the expedition by sailing for Santa Marta along the Main. In stormy weather, and with the fleet in danger of being dispersed, he changed course for Jamaica. With fourteen vessels under his command, Baskerville reached the southern coast of Cuba where, off the Isle of Pines, he met a Spanish fleet under the command of Bernadino Delgadillo de Avellaneda. Boldly challenging Avellaneda to a duel, Baskerville led the expedition into battle against the Spanish force of twenty ships. It was a hot contest, involving close action between rival fleets of warships. Although both sides claimed victory, the English sustained few casualties, inflicting greater damage on Avellaneda’s fleet. The English claimed that the latter was ‘sore beaten and racked thorough’.98 The Spanish shadowed the English ships, but they showed little desire to renew the conflict, enabling Baskerville and his company of survivors to leave the Caribbean for England.

  Soon after reaching the Scilly Isles in May 1596, Baskerville informed Burghley of the unexpected failure of the expedition. He returned with some silver and pearl, as well as ten Africans, who the council ordered to be transported out of the realm. As Baskerville anticipated, the plunder failed to cover the cost of the venture. Furthermore, he faced allegations of cheating the Queen out of £30,000, though he resolutely defended himself, complaining to his wife that he was at least £1,000 poorer as a result of the voyage.

  Baskerville explained the disastrous outcome of the expedition by drawing attention to the intelligence which the Spanish had of English plans. This appeared to raise deeper issues regarding the delayed preparations for the voyage, which touched on the Queen’s role, though understandably he refrained from making any comment on these matters. Additionally, he drew a veil over the problem of divided leadership, declining to offer any judgement on the command of either Drake or Hawkins. By contrast Maynarde drew subtle lessons from the failure of the voyage, which reflected on the wider conduct of the maritime campaign in the Caribbean. Without a base in the region, he argued that large fleets would accomplish little. Consequently, unless the Queen was prepared to ‘dispossesse … [Spain] of the Landes of Porterico, Hispaniola & Cuba,’ it was reprisal ships, the ‘filtchinge men of warre’, who were capable of achieving greater success and profit.99

  The last voyage of Drake and Hawkins was also the last expedition into the Caribbean in which the monarchy was involved as a major partner with private adventurers. By default the conflict in the region fell into the hands of the privateering interest. For the English, therefore, the Caribbean remained a crowded arena for private war and reprisals, creating the conditions for the subsequent growth of piracy and buccaneering. During the later 1590s the sea war also paved the way for the emergence of ventures which combined plunder with trade or logwood cutting. The Anne Francis of London set out in September 1598, carrying letters of reprisal, with the intention of acquiring a lading of wood. On the uninhabited island of Nevis the company, who served for wages, cut about 120 tons of logwood, pioneering a form of enterprise which was to be adopted and adapted by groups of rovers in other parts of the Caribbean.100

  Across the Atlantic the maritime conflict was reinvigorated by the emergence of Essex as the champion of the war party, in favour of offensive action against Spain. Drawing on the ideas of Hawkins, Drake and others, he promoted a coherent and compelling strategy designed to weaken the enemy while defending and enriching England. He relegated the significance of the reprisal war, eschewing the ‘ways of sharking seamen’, identifying the struggle with Spain as a contest over religion and liberty, rather than a disorderly pursuit for plunder.101 But profit was not neglected. Within a short time, ‘a great part of the golden Indian stream might be turned from Spain to England’, creating the foundations for an imperial monarchy which would enable Elizabeth to ‘give law to all the world by sea’. Apart from this powerful strategic vision, Essex’s plans appeared to contain an inherent social dimension which
anticipated the assertion of aristocratic control over the sea war, against the disorderly and embarrassingly piratical behaviour of private men-of-war. In that sense they drew on lingering ideas of chivalry which helped to sustain the ambitious enterprises of adventurers such as his kinsman, Robert Dudley, the illegitimate son of Leicester, whose search for the gold of El Dorado was also intended to burnish the mirror of knighthood.102

  As the survivors of the West Indies expedition returned during 1596, a major fleet was prepared for action on the coast of Spain. This was a royal venture, led by the Lord Admiral in association with Essex. Its primary purpose was to destroy shipping of the Spanish navy, to forestall aggressive action in Ireland, though it was also intended to plunder the Indies fleet. It was made up of more than 100 vessels, of which seventeen were from the Queen’s Navy, and carried a force of nearly 10,000 men. With Spanish coastal defences unprepared, the fleet sailed into Cadiz harbour, burning and sinking ships, including several galleons. But it missed the chance of capturing a fleet bound for the Indies, laden with goods reputedly worth twelve million ducats, which was sunk in the harbour to avoid its seizure and spoil. Nonetheless, the English took and held Cadiz for two weeks, during which it was extensively looted. A proposal by Essex to retain it, as a base to be used as a stranglehold on Spanish commerce, met with little support, and the expedition returned for England. Three vessels owned by Watts stayed behind, to lie off Cape St Vincent, hoping to acquire prizes. Although the Cadiz expedition was an impressive military and political success, which seriously embarrassed the Spanish monarchy, it was a financial loss for the Queen, whose share of the plunder amounted to little more than £12,000.103

  The following year a serious attempt was made to take and hold a base on the coast of Spain, though it ended in confusion and failure. With a force of seventeen royal vessels and 5,000 men, Essex was also instructed to destroy a Spanish fleet at Ferrol. The plan was changed after the original expedition was forced to return due to bad weather. Although Essex departed later in the year with a reduced force, the attack on Ferrol was abandoned in preference for a blockade of the Portuguese coast. But this scheme was soon surrendered. Instead, Essex sailed for the Azores in the hope of meeting the Indies fleet. Under Essex’s weak command, however, the expedition scattered at the islands, missing the fleet which reached Spain without loss. As the expedition returned to England, a Spanish force was within striking distance of the coast of Cornwall. Although it was battered by autumn gales, the threat to English security, combined with the incalculable risk of offensive operations, affected the subsequent conduct of the war at sea.104

  The expedition effectively ended Essex’s career as a sea warrior and strategist. Faced with the spread of rebellion in Ireland, against a background of increasingly hazardous international relations that included peace between France and Spain, the regime’s interest in offensive maritime action weakened, in favour of concentrating on essential defensive measures within the Channel. By 1598, the peace party at court appeared to be gaining the upper hand, though the war drifted on for another five years.

  Despite these changing conditions, the private war at sea flourished. A voluntary force of predators continued to expose alarming weaknesses within Iberian commercial and colonial networks. While a large and disorderly group of men-of-war haunted the Channel or congregated along the coasts of Spain and Portugal, others ranged into the Caribbean or the Mediterranean. There was also an attempt to build on Drake’s success in the South Sea, with an expedition of 1593 led by Richard Hawkins. Although he was captured by the Spanish, and held in captivity until 1603, the expedition underlined the persistent vulnerability of the region to opportunistic incursions. According to a report of October 1600, another adventurer, Captain Benjamin Wood, who had been at sea for four years, acquired a rich haul of booty in the South Sea, only to lose it all disastrously. During the return voyage the company ‘was driven to … [such] want that they were faine to eate one another, and forced at last to put into Porto Rico, where all that were left are taken and theyre wealth lost’.105 Even so, the relentless assault on enemy trade continued to pay rich dividends, especially for experienced mercantile promoters.

  At the same time the reprisal war continued to provide an opportunity for large-scale expeditions to be sent out by Cumberland, sometimes in association with the Queen but increasingly in partnership with London traders and shipowners. In effect these were auxiliary fleets which were intended to undertake offensive action against Spain and Portugal. Cumberland’s sea venturing culminated in 1598 with a major expedition to the West Indies, made up of twenty vessels. Outward bound the fleet cruised along the coast of Portugal, hoping to intercept rich carracks returning from the East Indies. The Portuguese insisted on describing Cumberland as an arch-pirate. Nevertheless, in May it was reported from the Iberian coast that ‘the small forces of an English Earl … shut in both the East and West India fleets’.106 Within the Caribbean, the expedition raided San Juan de Puerto Rico, gaining control of the island, which Cumberland intended to retain. The plan was given up, however, following the loss of about 400 men to disease. The expedition returned with several prizes, laden with sugar and ginger, valued at between £15,000 and £16,000. For Cumberland this was a financial disaster. The booty, one letter writer noted, failed to cover half of the charge of setting out the fleet. In addition the scale of the human casualties underlined the dangers of Caribbean venturing. Sustaining heavy losses, Cumberland withdrew from sea service. He retained an interest in several ventures on a much-reduced scale, which included associations with Sir Robert Cecil, Burghley’s son and political heir. In 1601 he promoted an ambitious, but abortive plan for a venture to use the island of St Helena as a base for the plunder of Iberian shipping.107

  Cumberland’s ventures dramatized the deep-seated ambiguities of the sea war, especially the tension between short-term profit and longer-term strategic goals. The balance between these distinct, occasionally complementary, but competing goals was destabilized during the latter part of the conflict, as the competition for plunder intensified between English, Dutch, French and Flemish men-of-war. During the 1590s private enterprise grew progressively parasitic, diverting resources, including recruits, away from royal service. While the navy resorted to pressing men, not always successfully, there was no shortage of volunteers prepared to serve aboard private ships. Under these conditions the character of the war at sea also began to change. On the one hand, as the conflict progressed, London’s share of reprisal venturing became more dominant. In part this was the result of widespread difficulties in the provincial ports, which were struggling to cope with the disruption and decline of trade. At the same time it reflected the greater concentration of professionalized and experienced adventurers among the merchants and shipowners of the city. On the other hand, the growing dominance of London was accompanied by increasing disorderliness at sea. To some extent this was an inherent characteristic of large-scale, organized depredation, particularly over a prolonged period. It was rooted in the organization of reprisal ventures, whereby recruits served for a share of the spoil, and fuelled by the greater freedom that prevailed aboard men-of-war. At times legitimate plunder provided a cover for piracy, though it became increasingly threadbare during the later 1590s and the early years of the seventeenth century.108

  Conditions at sea during this period became widely confused and disorderly. An unruly group of captains and their companies, who repeatedly came to the attention of the High Court of Admiralty or the council, ignored the regulations governing the reprisal war, provoking outrage and retaliatory action. Unlawful spoil was associated with violence, occasionally torture and murder, and was often concealed by the illegal disposal of prizes in overseas markets ranging from southern Ireland to north Africa. Those who engaged in it came close to mimicking the behaviour of pirates, following a path pioneered by Callice and others. In turn they established a pattern of roving which was to be copied or adapted by pirate groups operat
ing after the 1604 peace with Spain.109

  Among the victims, French traders and shippers continued to bear the brunt of this tide of disorderly depredation. But Dutch shipping was also subject to repeated spoil, as were vessels from the Hanseatic League, as well as from Denmark, Poland and Scotland. In addition, English and Irish merchants who continued trading with the enemy were exposed to attack, though Irish trade to the Iberian peninsula was unofficially tolerated because it provided the regime with valuable intelligence from Spain. In March 1597 a leading Dublin merchant, Nicholas Weston, who had two servants employed as spies in Spain, complained that one of his ships had been pillaged while returning from Bilbao. It was the fourth occasion during the year that one of his vessels was spoiled. As he informed Cecil, it was ‘very dangerous now to venture abroad, by reason of so many English men-of-war, which spare nobody that comes’.110

  The activities of unruly or unlicensed reprisal ships aroused a clamour of overseas protest. During the second half of the 1590s the council was faced with a stream of complaints from foreign merchants and shipowners against unlawful depredation or piracy. The nature of the problem is indicated by a sample of cases heard by the council from January to June 1596. During these months, among a wide range of other business, it dealt with grievances concerning the seizure or spoil of at least nine foreign vessels. Four of these ships were of French origin, while the rest were of Dutch or north European background. In most cases their capture was apparently justified by letters of reprisal, though the owners of goods aboard a ship of St Malo, taken during a return voyage from Lisbon, denied that it was lawful prize. Indeed, the spoil of two other French vessels led the council to issue warrants for the arrest of those involved, who it accused of piracy. In at least two cases an attack on neutral ships was accompanied by outrageous behaviour and conduct. Thus the Jonas of Rotterdam, returning from Malaga with a lading of sugar, wine and raisins, was violently boarded by Captain Morrice and his company, in a man-of-war set forth by Sir Thomas Norris. At some stage during this encounter, in obscure circumstances, the master and crew of the Dutch vessel were all slain, while the cargo was taken to Limerick to be sold. In a separate incident Captain Webb, in command of the Minion of Bristol, seized a ship of Danzig returning from Lisbon, the master and company of which were tortured and then cast overboard.111