Sir Francis Drake

The general minding to depart

Commands his men in haste aboard,

Then lifting up both hands and heart

Most thankfully they praise the Lord,

For giving them such victory

Without bloodshed or jeopardy.

THE WAR WAS coming. Most acute observers could see that. Philip II was not always a decisive man, and his removal to the monastery of San Lorenzo de Escorial, the great palace at the base of the barren Sierra de Guaderrama, seemed to emphasize his need for an isolated place in which to contemplate, to worship, and to plan. But as he sifted through the enormous piles of papers beneath the magnificent ceilings of the Escorial, or kissed the relics of the saints that he so assiduously collected, even he understood that a decisive confrontation between England and Spain could not long be avoided. He thought he knew how to handle it, too. Time seemed to be on his side. The union with Portugal had given him the basis of a fleet that could challenge Elizabeth’s navy, the beginnings of a vast armada, and Santa Cruz’s defeat of Strozzi and capture of Terceira suggested that at least he knew how to use it. The caution that had once warned Philip against antagonizing England while France was still a powerful rival also diminished as the French slid towards another civil war. After the death of Elizabeth’s French sweetheart, Alençon, his brother, the king, had no obvious heir except the Huguenot Henry of Navarre, and the Catholic League and the influential Duke of Guise were willing to accept Spanish money to oppose him. Divided, France was less of a problem. And the Netherlands? The champion of the Dutch, William of Orange, was dead, struck by an assassin’s bullet in 1584, and Parma’s mixture of diplomatic and military skill was slowly reducing the rebellious provinces to order. Even now he was poised for his most dramatic achievement, the capture of Antwerp, one of the last pockets of resistance south of the Maas. A conviction was growing in Europe that the war in the Netherlands was reaching its finale, one which would leave England bereft of useful allies and staring across the Channel towards a hostile coast, standing almost alone in the path of Spain. Then, Philip reckoned, would be the time to deal with the heretical queen and her pirates.

In England that summer of 1585 Dutch envoys begged for help to save Antwerp, urging Elizabeth to intervene more decisively in Europe while there was still time. As a monarch she might resist encouraging rebellion against a legitimate king; as a housekeeper she shrank from the expense of war; but as a patriot, a sovereign of her realm, could she see the Dutch fall for want of friends when the result would have been England’s isolation? She wavered, but then in June a little London trading bark, the Primrose, returned home with a fearful tale of Spanish treachery that raised outrage throughout the country. Like many another foreigner, the Primrose had been exporting grain to Spain, where the crops had failed, but in May Philip suddenly declared an embargo on English vessels in Spanish ports, and had them stripped of their arms, munitions and tackle to equip his fleet at Seville and Lisbon. The Primrose was boarded in the Bay of Bilbao, but fought free and escaped, and when she reached England her crew were able to show a document they had captured, which was no less than Philip’s instructions to Spanish officials for the seizure of English ships.

In the rising indignation Elizabeth was pushed into action. She did not declare war, at least not directly, for she clung to the increasingly tattered notion that acts of war need not necessarily mean war. They might be legitimate but limited reprisals for injuries, such as Philip’s embargo or the involvement of his ambassador, Mendoza, in a recent plot against the queen’s life, and yet fall short of all-out conflict. But she went further than she had ever done before: she agreed that an army must be sent to the Netherlands to prop up the ailing Dutch rebellion until Philip would grant satisfactory terms, and she unleashed Sir Francis Drake upon the Spanish coast. Now, for the first time, the great sailor was given the queen’s commission, signed in July 1585 and authorizing him to visit the ports of Spain to release the English ships and crews impounded by Philip. Better still, as far as Drake was concerned, commissions of reprisal were issued to merchants whose property had been lost in Spain, enabling them to recoup their losses by plunder. Under their colour, Drake could rove in search of booty and honour wherever he chose.

A document endorsed 25 April, 1586, but probably prepared the previous November, suggests the itinerary Sir Francis had tentatively set himself. He planned to raid the Cape Verde Islands, cross the Atlantic and reprovision at Dominica before the end of November, and then capture Margarita, Santo Domingo, Rio de la Hacha and Santa Marta in the next month. During January and February he might be able to reduce Cartagena, Nombre de Dios and Panama, the last with the help of 5,000 cimarrones Drake hoped to recruit in the isthmus, and the fleet would conclude the campaign with the capture of Havana. Since most of the English ships seized by the Spanish had been released before Drake reached the Spanish coast, there seemed to be more time for what was, in fact, an over-imaginative and overcrowded schedule that left no room for misadventure.

Ambitious it was. And it exemplified the combination of strategic and economic motives that underlay so much Elizabethan endeavour. If it succeeded, Spain would be virtually ripped out of the Caribbean by the roots, and there was even a suggestion that the English might leave a permanent garrison in Havana themselves. The profit motive also ran through the entire document, which bristled with optimistic allusions to the expected returns: Santo Domingo would yield 500,000 ducats; Cartagena, a million ducats; Panama, a million ducats, and so on. This mercenary footing was inevitable in an expedition that cost more than £60,000 to outfit and was funded by private enterprise, but it was not, it should be noted, incompatible with strategic or national interest. Although sometimes described as a grand privateering raid, Drake’s voyage was not motivated by purely commercial ends. Money was needed by the queen to finance her new initiative in the Netherlands; very well then, let Drake supply it. And, with Philip starved of his American treasure, it was supposed that his military offensive in Europe would come to a halt. ‘That,’ chirped Leicester to Burghley, ‘is the string that toucheth him indeed, for whiles his riches of the Indies continue, he thinketh he will be able with them to weary out all other princes. Those taken away, himself will quickly fall. And I know by good means that he more feareth this action of Sir Francis than he ever did anything that hath been attempted against him.’¹ Drake and his collaborators were fully attuned to the political dimension of their new project.

The composition of the fleet Drake assembled between June and September reflected the entrepreneurial side of the enterprise. It would be a joint-stock venture, in which the queen contributed two naval vessels, the Elizabeth Bonaventure of some 600 tons and 250 or more men, and the Aid of 250 tons. The Bonaventure was not new. Purchased from a Hull merchant in 1567, she had been rebuilt, but painted in black and white, and, the largest ship in the fleet, she looked impressive, ‘the best conditioned ship of the world,’ thought Thomas Bayly.² Drake took her as his flagship, and appointed as her captain Thomas Fenner, one of the famous seafaring family, and a thorough professional. The Aid was commanded by Edward Winter, son of Sir William and cousin to the John Winter who had sailed with Drake to the Strait of Magellan.

As usual court and peerage were well represented. The earls of Rutland, Shrewsbury and Bedford seem to have invested money in the venture, and Shrewsbury supplied the Talbot bark. Leicester contributed the Galleon Leicester, commanded by his brother-in-law, Francis Knollys, and the tiny Speedwell. Some of the main investors were connected with the navy. Sir William Winter provided the Sea Dragon; the Lord Admiral, now Charles, Lord Howard of Effingham, the White Lion, captained by James Erisey, a West Country man; and the Hawkins brothers, the Bark Bond (Captain Robert Crosse), the Hope, the Bark Hawkins (Captain William Hawkins the younger), probably the Galliot Duck (Richard Hawkins), and possibly also the Bark Bonner, whose captain, George Fortescue, had been one of Drake’s circumnavigators. A number of the vessels, fitted by Drake himself, reflected the names of their owner’s family. The Thomas Drake (formerly the Bark Hastings) was commanded by the brother whose name she bore. Thomas Moone of Plymouth, who shared all of Drake’s voyages, took charge of the Francis, and the Elizabeth Drake, often called ‘the little Elizabeth’ to distinguish her from the Bonaventure and captained by John Varney, proclaimed Drake’s new lady to the world.

Most of the remaining ships belonged to the merchants of London and Plymouth. The Town Corporation of Plymouth ploughed some money into the voyage, but the most important merchantmen were the Primrose and the Tiger, both apparently the property of the City traders. The 400-ton Primrose served as vice-admiral under that hard-nosed seaman (‘harsh and violent’ someone called him) Martin Frobisher, while the 150-ton Tiger was commanded by a stepson of Walsingham, Christopher Carleill, the lieutenant-general of the expedition. All in all, it was an imposing fleet, some twenty-five ships and eight or more pinnaces, the largest England had ever sent from home waters.

Drake was equally satisfied with his personnel. The captains of the Thomas Drake, Francis, Bark Bonner, Bark Hawkins, and Benjamin had sailed with him around the world, and he could vouch for them, while others, like Edward Gilman of the Scout, James Erisey and Richard Hawkins, were well known to him. The twelve companies of soldiers, who formed a great part of the two thousand or more who composed Drake’s force, were largely inexperienced and unskilled, but Carleill knew his business, and with his sergeant-major, Anthony Powell, and two ‘corporals of the field’, Matthew Morgan and John Simpson, would soon knock them into shape. Prima donnas were less welcome, however, and Sir Francis suddenly found himself lumbered with two men who epitomized everything in Elizabethan gallantry: poets, politicians, courtiers both, Sir Philip Sidney and Sir Fulke Greville, hotfoot from London to Plymouth and waiting to sail. Drake’s heart must have sunk.

Sidney had sat with Drake in Parliament and was, besides, Master of the Ordnance, so Drake knew something of him. He also remembered Sir Philip’s father from his service in Ireland, and even better the poet’s uncle, none other than Leicester himself. Sidney’s spirit and generosity probably appealed to Drake, but was he capable of the serious business in hand? Besides, the queen knew nothing of her favourite’s flight, and was sure to take it badly. Sidney and Elizabeth were not on the best of terms. He was disappointed at her failure to appoint him Governor of Flushing, and rather than kick his heels at court in pique he wanted to sail away without the courtesy of consulting his sovereign. Not only that, but neither Greville nor Sidney was likely to remain unobtrusive. Somehow Greville got himself named as captain of the Hope, and Sidney began interfering by insisting that one of his protégés should replace old William Hawkins as captain of the Sea Dragon. Drake’s instinct for survival in a world of patronage, and his unfailing attention to the great, forced him to make the switch, but to salve the old man’s feelings he took Hawkins aboard the Bonaventure as his own assistant. He owed far more to this veteran sea dog than ever he would owe Sidney.

As if Sidney and Greville were not enough, there now turned up another recruit, the mercurial Dom Antonio, fresh from adventures in France and ready to meddle anew in English affairs. Drake unloaded both Sidney and the pretender on his wife at Buckland Abbey, and while Lady Elizabeth played hostess he grappled with the problem of getting rid of them. He dare not offend the queen by taking Sidney. Twice before, in 1581 and early in 1585, he had laboriously set voyages afoot which Her Majesty had suddenly suppressed for one reason or another. And so he prosecuted his preparations with the greatest speed, and – if Greville’s reminiscences are to be believed – secretly allowed the queen to discover that Sidney was with him. As he anticipated, she immediately recalled him, and without waiting longer than it took to disembark Greville and Sidney from the flagship Drake sailed from Plymouth with a fair wind on Tuesday, 14 September, 1585. His departure was so hurried that victualling had not been completed and at least one captain, John Martin, had his commission signed the same day. However, while the courtiers returned to Buckland, which both they and Dom Antonio shortly left for London, Sir Francis led his expedition unfettered into the Channel.³

For the first time Drake was trying his hand at managing a large force. The afternoon of sailing he assembled his principal officers aboard the Bonaventure to determine procedures to govern the fleet, and the next day the captains and masters received their sailing directions. Drake developed the practice of using them as advisers while confiding more closely in his vice-admiral and lieutenant-general. ‘For my own part,’ admitted Carleill of his commander, ‘I cannot say that ever I had to deal with a man of greater reason or more careful circumspection.’⁴

Everyone knew that the first priority was supplies. Because of the military character of the expedition, the total man-tonnage ratio was high, one man to one-and-a-half tons, and the hasty sailing had prevented the completion of watering and provisioning.⁵ Drake would not risk putting into an English port in case even there the queen’s caprice aborted his adventure, and trusted to finding a haven in France or Ireland. His luck held. On the 22nd the Bonaventure and Tiger tried to outsail each other in pursuit of a Biscayan ship laden with fish, and it was Carleill who overhauled her. Equipped with her cargo, Drake had enough food to run for Spain, where he planned with his usual bravado to force his enemies to make good his shortages. Within a week of the capture of the Biscayan the English were sheltering near the mouth of the Vigo River in north-western Spain, where Sir Francis submitted two questions to the local governor at Bayona: was Spain at war with England, and why had Philip impounded English ships?

Don Pedro Bermudez had a problem indeed, for here on his doorstep was the most feared of Englishmen with a great fleet at his disposal. The towns of Vigo and Bayona were at his mercy, and Drake was obviously considering an attack. Some of his men were landed on an island, where they destroyed the images in the chapel, while the admiral himself took Carleill in a rowing boat to inspect the defences of Bayona. But Bermudez was not ready for a showdown, and replied courteously. He knew nothing of a war, he said, and although English shipping had been seized he announced that they had now been released. He went further still, and sent provisions to the English to signal his goodwill – bread, wine, oil, grapes and marmalade.⁶

Drake remained in the river, for the weather was stormy, and on the 28th the sea was so difficult that when the admiral’s skiff was sent out in emergencies her crew were promised extra pay. Some of the ships lost their cables and were in danger of running ashore, so they put out to sea and one of them, the Speedwell, returned to England. As the weather improved, Drake moved his force up-river to threaten the town of Vigo and seize a small number of boats and caravels. Fearing the worst, the governor assembled about 1,000 horse and foot on the shoreline where the English fleet rode at anchor, and agreed to confront the formidable corsair face to face. There followed a curious pantomime. Drake sent two volunteers, Captain Erisey and Captain Crosse, to the Spaniards as hostages, and Bermudez was then pushed off in their boat and rowed towards the ships. A handkerchief was raised at the water’s edge as a signal, and another small boat appeared, pulling from the Bonaventure. In it was Francis Drake. He met Bermudez midway between the fleet and the shore, and they parleyed for two hours in the admiral’s boat, rising and falling upon the swell. When it was over Drake had what he wanted. He had agreed that the English would leave Bayona and Vigo alone, provided his men could provision and water ashore without molestation.

It must have been an unusual sight, the fraternization that ensued between Englishman and Spaniard, Protestant and Catholic. Drake’s men went ashore and rubbed shoulders with the natives, gathering their provisions, while a few Spaniards visited the ships to discover that the terrible dragon of the sea was far from inhospitable. Then, on 11 October, the fleet was gone. Behind it Spain fumed at the humiliation. That Drake should dictate terms on Spanish soil was bad enough. That he should secure Spanish provisions so that he could threaten Spanish possessions made it worse. The king was ill, but his council debated the matter for three consecutive days. Philip’s admiral, Santa Cruz, was also in a sweat. Drake, he said, might sweep the Brazilian colonies, raid the Pacific or ravage the West Indies, for there was no force in the whole of the Americas equal to the one he had brought from England. Panama, Santo Domingo, Puerto Rico, Cartagena, Havana and Nombre de Dios – Spain’s key strongholds in the Caribbean and on the isthmus – were all at risk. The communications between Spain and the West Indies could be severed, and the flotas commandeered. The trouble was that no one knew whither he was bound. Philip, when he addressed the problem, could do little to solve it. He prayed that the flotas would reach his kingdom safely, and sent word to the West Indies that Drake was loose. He ordered the convoys bound for the west to remain in Seville, and directed Santa Cruz to defend the coasts of Spain. But the truth was that once again Drake had exposed the weaknesses of Philip’s empire. Spain had certainly improved her defences, both in the Pacific and the Caribbean, enough to contain the sort of corsairs that had hitherto troubled her colonies. Yet there was nothing that could handle a fleet such as Drake commanded. By raising the scale of the operations and the level of potential violence, Sir Francis had remained ahead of the game.

For a time it seemed that he might achieve the unthinkable, and capture a homeward-bound treasure flota, but he had tarried too long. That bad weather that had penned him in the Vigo River and the necessary but lengthy provisioning had cost him the opportunity. His remarkable good luck deserted him. The Mexican flota had sailed in July, tired of waiting for the Peruvian fleet to join it at Havana, and slipped home in September. The Peruvian flota was among the richest known, but it ran late, and did not reach Terceira in the Azores until 7 October, when Drake was at Vigo. However, it made San Lucar in the middle of the month as the English were cruising several miles to the north-west, off the Portuguese coast. Drake had missed his prey by a short run indeed, according to his own estimate by a mere twelve hours!

It was a decisive misfortune nonetheless, for it left the admiral without his richest prize. All he could do now was to descend upon the West Indies after the bird had flown. The afternoon of 3 November found the fleet off the Isle of Palma in the Canaries. After conferring with his officers Drake made an attempt to capture the town there, but rough seas and the vigilance of the enemy promised a resistance too stiff for this stage of the voyage. Several pieces of artillery were fired at the ships as they approached. The first shot passed over the Bonaventure, but the second was a direct hit. It swept between the admiral’s legs, passed Frobisher and Carleill who were walking with him, and smashed into the wooden gallery throwing out splinters which slightly hurt another officer, George Barton. Other shots struck the Aid and the Leicester, and the flagship received a second ball, close to the waterline. Drake judged it injudicious to attempt a landing, and sailed instead for the Cape Verdes.

His descent upon these Portuguese islands, now united with the Crown of Castile, has been described as a diversion, although since no comprehensive plan of the voyage survives it is difficult to say whether it was part of Drake’s itinerary or not. In any case, it was fairly usual for Elizabethan voyagers to make the Atlantic crossing from the Cape Verdes. Having said that, Sir Francis maybe had something else in mind. He was a man who nursed grievances, and constantly justified his private war against Spain by reference to the treachery of San Juan d’Ulua. Against Santiago, the capital of the Cape Verdes, he also had his complaints, for in 1582 the ships of William Hawkins, in which Drake had invested, had been rebuffed there, apparently through some kind of deceit. Little is known of Hawkins’s defeat, but it was said that English lives had been lost, and it would be entirely in Drake’s character to have decided that the time had come to square the account.

Santiago was situated on the south-western side of the isle which bore its name, and consisted of several substantial houses and a population of perhaps 2,000 people. It lay in the mouth of a low narrow valley, flanked by cliffs and hills, with the sea towards the south. There were numerous gardens, rich in coconut and date palms and fig, lemon and orange trees, but the island’s economy was much dependent upon sugar cane, cotton and silk. As for defence, looking seawards there were two batteries near the harbour, and a third covered the western approaches to the town. In all, these ‘forts’ mounted fifty to sixty pieces of artillery, most of them brass, but they were not in good shape and the town was vulnerable, especially from the east, where no effective works had been established.

Santiago had been unfortunate these past few years, for it had fallen not so long since to French corsairs. Drake dealt it a far harder fate. In the evening of 17 November he landed some 1,000 men under Carleill, east of the town, where they could strike at its weakest point. Then, while his soldiers were scrambling through the darkness over the difficult ground towards Santiago, he took the fleet to menace the harbour and divert the attention of the defenders from the true point of the attack. As it happened the army was not needed. The shore batteries opened fire upon the English ships, but the defence was ill spirited and the townspeople were soon fleeing westwards with their valuables, leaving behind only a few civilians and about twenty-six sick Negroes in the hospital. When Carleill’s force reached the town they found that the opposition had fled, and it took but a little time to raise the flag of St George over the principal buildings.

There was little plunder to be had. Seven ships in the harbour were deprived of various commodities and one of them was added to the fleet. Ashore, Drake’s men took off the artillery, along with powder, oil, cotton, silk, victuals, fruit and water, even the bells of the steeple. But Drake hoped for a better return by ransoming the town, and sent a Portuguese who had appeared under a flag of truce to find his governor, with the message that unless negotiations were opened to decide upon what sum would be paid to save Santiago he would raze it to the ground. There was no response to his threat, and Drake did not hesitate to carry it out.

While his men occupied the town, Drake led six hundred soldiers to a nearby village called Santo Domingo. It was a tiring, fruitless episode, for its inhabitants had fled into the countryside taking everything of value with them. The English burned the village, and trudged back to Santiago, Drake and Carleill looking not a little ridiculous as they took turns riding an ass. Parties of enemy horse and foot hovered around, too weak to interfere, but they did pounce upon a straggling English boy and cut off his head and carved out his insides. The next day, 28 November, Drake dispatched another force to Porto Praya, a settlement of less than a thousand inhabitants east of Santiago, and then supervised the evacuation of the city itself. With unflinching severity he ordered it destroyed, sparing only the hospital, a warning to those who would not treat with him that he meant his word. Harsh it was, although understandable. Drake’s expeditions owed their existence to investors looking for a financial return, and he needed to impress his adversaries that they would have to pay to save their homes. His single-mindedness on the subject was seen soon afterwards, when the fleet reached Porto Praya on the 29th. His men had taken the town, but obtained nothing more worthwhile than two pieces of artillery, and the inhabitants had fled. Drake ordered that it, too, be put to the torch.⁷

To account for such booty as they had acquired, Drake had already laid down instructions governing the conduct of the land forces, enjoining that neither chest nor door be broken open without the authorization of Drake or an appointed officer, and that officers ensure that none of the plunder be purloined for private use. One article will suffice to indicate the flavour of the regulations:

Item, for as much as we are bound in conscience and required also in duty to yield an honest account of our doings and proceedings in this action … persons of credit shall be assigned, unto whom such portions of goods of special price, as gold, silver, jewels, or any other thing of moment or value, shall be brought and delivered, the which shall remain in chests under the charge of four or five keys, and they shall be committed into the custody of such captains as are of best account in the fleet.⁸

Drake may have been an entrepreneur, hungry for profit, but his fault mirrored that of the Elizabethan government, court and city that had backed him, and to which he owed his command. Private enterprise, encouraged by the State, had delivered his voyage, and he must perforce satisfy its expectations.

It was in connection with his regulation of the fleet that Drake experienced the insubordination that always infuriated him, and again at its root were men of birth accustomed to privilege and command. The disaffected coalesced around Francis Knollys, captain of the Galleon Leicester, a man of impeccable connections, the son of the Treasurer of the Household, and a blood relative of the queen herself. By marriage he was also related to Leicester. Knollys was not without experience of the sea, but he owed his appointment to the expedition to patronage, and evidently considered himself indispensable to its success. Perhaps Knollys believed that he should have had more to do with the running of the fleet than Drake allowed. He had not always been privy to the admiral’s decisions, nor been included in all the councils. That the journal of his ship, written by one of his supporters, has such harsh words for Drake and Carleill is indicative of the jealousy he bore them.

While the fleet was at Santiago Knollys found fresh fuel for his resentment. The Leicester journal records that Drake had disposed of the cargoes of the ships taken there no one knew how, and that Carleill had distributed unequal shares of plunder among the soldiers and quartered himself and his land captains in the best houses. If Knollys had originally taken offence at the lack of deference paid to his position, his anger had spilled into charges of corruption. We hear from his ship’s journal that much personal plunder was carried aboard the fleet at Santiago. Again, the complaint is clear: the regulations were being flouted, and Drake and Carleill were to blame.

But perhaps it was a curious ceremony of 20 November that first alerted Drake to the problem. He had asked his chaplain, Philip Nichols, to draw up oaths of loyalty which acknowledged the sovereignty of the queen, bound Carleill and the fleet captains in obedience to Drake, and the men in a like condition to their captains. There is no suggestion that Drake produced the oaths other than as a routine assertion of his authority, and highly unlikely that he considered that any of them would be found offensive, for they simply acknowledged the authority structure that already existed in the fleet. However, after Drake had read out the articles of the oaths, he found one captain, and only one, who demurred to swear to them. Francis Knollys declared that he would surely swear to the supremacy of Her Majesty, but he would put his name to no other oath. Drake was probably surprised, particularly inasmuch as Knollys could offer no explanation for rejecting an oath that simply bound him to serve his admiral. The obvious inference was that he did not consider it his duty to obey Drake. We can imagine the fiery Devonian’s eyes narrowing at the thought.

For a while the Knollys episode was the talk of the fleet. There was an altercation between Nichols and Knollys, in which the latter murmured incoherently about oaths ‘dangerously like to hazard many men’s souls’, as if there was a religious dimension to his opposition.⁹ The chaplain was not impressed, and the next day, 21 November, being a Sunday, gave him his platform to reply before the whole company. During his sermon Nichols remarked that any who refused to take the oaths were unworthy of the enterprise upon which they had all embarked. This stung Knollys to the quick. After dinner he confronted the chaplain in Drake’s presence, assisted by one of his friends, Master Thoroughgood, but the admiral brought the argument to an end by an outburst of fury. He swore that while he could speak for the loyalty of his chaplain, he had no faith in Knollys and Thoroughgood, who had refused the oaths and now sowed sedition and faction. Thoroughgood hardly knew the memories conditioning Drake’s thinking, but protested that he was as ready to serve as any. Drake would not have it, and accused Knollys of raising a party against him. ‘Yea,’ he said. ‘You are their defender and maintain them against me.’¹⁰ The affair had become ridiculous. Drake was looking at Knollys and seeing Thomas Doughty, unable to understand his objection to the oath. For his part, Knollys could no more explain it. It was probably an emotional response, a gesture of non-co-operation that arose from his resentment at being slighted during the voyage, but one he found difficult to justify in rational terms. Confronted by a choleric display on the part of the admiral, he assured Drake of the loyalty of his men and suggested that it might be better if they were given a ship to go their own way.

Sir Francis’s instinct told him to deal decisively with the matter, and the following day he had every man of the Leicester assembled before him and the other captains of the fleet. To them Drake put only one question. Would they stay or return to England with Knollys? Most of them agreed to remain, but Knollys found forty or fifty in his support, and Drake forthwith declared them exempt from further service. He said that he would provide them with a vessel, the Francis, and dismiss them. And yet he was unhappy with this solution. He was satisfied that he had unearthed the core of the opposition, but the more he thought about them sailing away, beyond his control, perhaps alerting the Spaniards by plundering, perhaps being captured and revealing what they knew about Drake’s intentions, the less he entertained the idea. On the 23rd he sent Knollys three articles to which he required written answers. Would he place his company at Drake’s disposal? Was he resolved to leave this service of the queen? And if he was relinquished would he return directly to England? Drake wanted a written acknowledgment that the captain had surrendered his command to the admiral, and returned of his own free will, and he wanted a guarantee that Knollys would not loiter where he could do harm.

On the first and last points Captain Knollys’s reply was satisfactory, but the response to the second article was more equivocal. He was unwilling to depart, he affirmed, but rather than be considered ‘a mutinous or faction person’ and thereby ‘an hinderance’ to an expedition ‘which I desire God to bless and prosper’, he desired ‘not only to be out of the society but under the waves as deep as there is any bottom.’¹¹ Drake was still unhappy. Knollys was, after all, not uninfluential in England, and the admiral was reluctant to send him home under a cloud. Although the decision had been endorsed by some of his principal officers, Drake decided to delay enforcing it. Instead, he divided Knollys’s supporters among the other ships, where he hoped they could hatch no mischief. The details of this affair have only recently been brought to light, and sharpen our understanding of Thomas Doughty’s legacy. The events of Port San Julian weighed heavily upon Drake’s shoulders. His extreme sensitivity to insubordination indicates how deeply his emotions ran. Now, at Santiago, those emotions had driven him to engineer a ‘mutiny’ that should never have occurred. There had been no need of the oaths of loyalty. If they had ever been necessary, they should have been administered in Plymouth, where dissenters could have stepped back without detriment to the voyage. They had simply created and advertised a situation in which up to fifty men had been forced into an act of public disobedience. Probably it would have been far better to have permitted the petulant Knollys to fester privately for the duration of the voyage. But it could not be undone.

There was soon a more serious matter to hand, for after quitting the Cape Verdes the fleet was struck with a virulent disease, and as the ships made their way across the Atlantic it advanced alarmingly. At one time a hundred men were down with it on the Bonaventure and sixty aboard the Primrose, something like a third of their companies. Two or three hundred men died in a few days, and many others were debilitated, left temporarily weak in body and mind. It was assumed that the disease had been caught at Santiago, but its cause is obscure, and some of the symptoms, the feverishness and spots, indicate that it may have been typhus fever and the product of the insanitary and crowded conditions on board ship rather than a tropical contagion. Drake monitored its progress, and counselled each ship about its management, but it pursued him to the West Indies. A landfall was made in the Leeward Islands, where valuable supplies were loaded, and then the fleet halted at St Kitts. It was uninhabited, and the men could be brought from the fetid ships to rest ashore while cleaning and fumigation took place. The fever began to recede, but even so twenty men were buried on the island.

Despite his reduced force, Drake decided to attack the city of Santo Domingo, situated on the estuary of a river in south-eastern Hispaniola. ‘The flower of the west’, a contemporary called it; it was the oldest Spanish city in the New World, once the capital of Spain’s colonial empire and still comparable in size to most cities in the mother country herself. Santo Domingo was partly sustained by the island’s substantial sugar and cattle industry. It boasted sedate and elegant buildings, a cathedral, three monasteries and two nunneries. Yet there was another face to Santo Domingo, one of decline and complacency. It was no longer part of the bullion route, and functioned largely as an administrative and legal centre, and the enervating sunlight in which it lazed revealed the decay of many of its houses. It had been fortified for more than a century, enough to deter the grosser ravages of the corsairs, but it was only strong towards the sea, where a bar protected the harbour and a fort. One governor proclaimed the fort among the strongest in Christendom, perhaps because it sported more guns than any other in the West Indies, but it possessed neither a regular garrison nor an adequate supply of powder. The little powder that was available was so poor in quality that it could scarcely project shot as far as the waterfront. Another battery had been established on the sea front in 1571, but on the whole the city’s defences were a fair reflection of Santo Domingo itself: an ageing façade waiting to be exposed.

The governor and captain-general, Licentiate Cristóbal de Ovalle, President of the Audiencia, had no professional soldiers to defend the city and depended upon a civilian militia, about eight hundred in the town and its environs, and more in the interior of the island. The numbers that opposed Drake are not known. A Spanish officer, but not one who was present when the English appeared, said that ‘there were more than 3,000 men, burghers and transients’ capable of being mustered.¹² The governor himself was reluctant to admit so high a figure, and reported that about 1,500 met Drake’s attack. Whatever the number, they had no will to fight. Most of them fled, and the bare two hundred or so who gave the principal resistance were poorly armed, many of them carrying only rusty pikes and swords. As for the naval force at Santo Domingo, there was only one galley, and it was unseaworthy.

Away from the sea the situation was even worse, despite the fears some citizens harboured of a rebellion by the several thousand blacks, mixed bloods and Indians who inhabited the island. The Spaniards had started walling the western and northern boundaries of the town, but the work was unfinished, dogged by financial problems and disputes about how far to the west and north the wall should actually run. In any case, some did not take the threat of attack from the west, at least from Europeans, very seriously. A practical landing place surely existed ten miles in that direction, at the mouth of the Hayna River, but it was only approachable through dangerous reefs and a heavy surf, and the path from the Hayna to Santo Domingo threaded through difficult jungle. So complacent were the Spaniards that when Drake arrived the wall amounted to only a few short stretches flanking the western gate, and there was no regular watch at the Hayna.

These were serious flaws to present to a man like Drake, who had spent fifteen years wiping smiles from smug faces. Now it was the turn of the West Indian cities to learn that lesson, and as his fleet passed through the Caribbean he had a useful piece of good fortune. From two or three prizes made on his way to Santo Domingo, he captured a useful pilot and the letters Philip II had sent to the West Indies warning them of Drake’s approach. Santo Domingo was caught napping. The city had heard that an English force had put to sea, but knew not where it was bound. And although a fishing boat reported seeing a large fleet nearby on 31 December, it was not until nightfall that an investigating frigate returned with the fearsome tidings that the ships were probably English. By then it was too late.

Santo Domingo fell in one New Year’s Day. In the early hours, while it was yet dark, Sir Francis Drake personally piloted his soldiers through the difficult shoals and surf at Hayna, and landed them from pinnaces and small boats before returning to his fleet to lead it to the city.¹³ There the governor was dithering nervously. A force was rudely assembled during the night, and Ovalle’s officers strengthened the harbour by sinking three ships on the shallows of the bar and positioning the solitary galley where her guns could rake an intruder. Earthworks were erected ashore, one with a parapet and cannon. Yet so little confidence did the Spaniards have that many began fleeing the city before it was light. When the sun rose that 1 January, 1586, it revealed Drake’s fleet tacking into position off the bar, while westwards, and still undiscovered by the enemy, were Christopher Carleill and his men, marching purposefully to the admiral’s support.

Now Sir Francis realized how weak this great city was, for when the supposedly formidable forts opened fire their shot fell short, apart from one that crashed through the Bonaventure. Even when the English pressed close to the waterfront and began sweeping the town’s defences with their artillery – one cannonball killed a Spaniard in his house – they suffered nothing in the reply. While Drake worried the city, drawing its attention, Carleill brought his men forward in good order, and it was not until noon that his approach was detected. A scrappy force of horse and foot came out to skirmish, but they were driven back by English arquebus fire. Then the Spaniards drove a herd of cattle towards the invaders, hoping to break their formation, only to see the frenzied animals scatter into the brush. Before long Carleill’s troops were gazing upon the gates to the city. There were two of them on this west side, the Lenba or main gate, and another, nearer the sea side, and they were pitifully defended by the few Spaniards who had not already fled, possibly less than two hundred indifferently armed men. They proved no match. Carleill led a part of his force against the main gate, while Captain Powell’s column stormed the other, and neither met appreciable opposition. Casualties did not exceed four killed on either side before the English surged through into the town, scattering the Spaniards before them. By the end of the afternoon St George’s ensign was fluttering above the royal palace and the church of Santa Barbara, and the city’s officials had fled, including the governor. Ovalle had been conspicuously absent during much of the fighting, and it was said that his horse had fallen in a muddy street and he had gone to his house for a change of clothes. Nevertheless, when he quit the town he left his wife and nieces behind. The only remaining pocket of resistance, the fort, held out until nightfall, but it was not prepared for an attack from the land, and the men evacuated it during the darkness, some flying up-river in boats and a few becoming captives of the English.

Drake had his men erect defences and batteries to deter any counter-attack, and made his headquarters in the cathedral. The privateers set to looting, rifling private homes and public buildings, desecrating the churches of the hated Papists and gutting the cathedral of its ornaments and images, its crucifixes and bells, and turning two of its chapels into common gaols. It did not take long to discover that the wealth of Santo Domingo had been overestimated. A good deal of plunder was obtained – hides, victuals, wine, vinegar, oil, olives, livestock, and some money, including 16,000 ducats from the royal treasury – but the haul was disappointing. However, there was still the matter of a ransom. On 12 January the High Sheriff of Santo Domingo, Juan Melgarejo, came to see Drake, authorized by the homeless Audiencia to negotiate a sum to save the city from destruction. Drake’s opening bid was one million ducats, but although talks went into the night Melgarejo insisted that that sort of money was simply unavailable. Sir Francis wanted to make sure that he was not lying, and after the sheriff had left he began to apply a grim form of pressure. First he had a chapel a mile north of the town set on fire, and then he detailed men to begin a systematic destruction of Santo Domingo itself. The work was hard, because most of the buildings were of stout stone, and days were passed in laborious toil.

But there shortly came the king’s factor, Garcia Fernández de Torrequemada, to reopen the discussions. Argument and counter-argument followed, and the factor was allowed to send someone to assess the worth of the remaining houses. At the end of it Drake could only get 25,000 ducats, and he had to threaten to suspend negotiations to secure even that amount. It was not an inconsiderable sum, and, with the money from the royal treasury, raised the English takings to an equivalent of £11,275, but it was far less than the privateers had anticipated.

While he was haggling with Drake, Philip’s factor was able to observe the most legendary of Englishmen at close hand, and later committed his impressions to paper:

Francis Drake knows no language but English, and I talked with him through interpreters in Latin or French or Italian. He had with him an Englishman who understood Spanish a little and sometimes acted as interpreter. Drake is a man of medium stature, blonde, rather heavy than slender, merry, careful. He commands and governs imperiously. He is feared and obeyed by his men. He punishes resolutely. Sharp, restless, well-spoken, inclined to liberality and to ambition, vainglorious, boastful, not very cruel. These are the qualities I noted in him during my negotiations with him.¹⁴

Who will gainsay that it is not an accurate portrait! One remark, in particular, calls for attention: that Drake was ‘not very cruel’. The significance of it can only be gauged from the fact that it was written by a man who must have been familiar with the most barbaric act of Drake’s career. Despite it, Torrequemada recognized that, within his context, the English commander was not inhumane.

There are three accounts of the ferocious incident that occurred during Drake’s occupation of Santo Domingo. The central figure in it was a black boy attached to the English side. He may have come with the fleet, or been one of the galley slaves Drake liberated when he captured the city. He may even have been among a number of blacks who came from the interior to join the English. With exaggeration it was reported in Europe that Drake ‘behaved with such humanity to the Indians and Negroes that they all love him and their houses were open to all English.’¹⁵ Whoever he was, the boy was sent by Drake to the Spaniards to carry a message under a flag of truce. One of them took offence. Perhaps he recognized a former slave. Perhaps he merely condemned the envoy because he was a black man. He took a lance and thrust it into the boy’s body. Mortally wounded, the messenger struggled back to the city and died at Drake’s feet.

The admiral rose in the grimmest fury, and nothing he ever did matched the ferocity of his vengeance for the Negro boy. He had a few prisoners in the cathedral, and he ordered two Dominican friars, harmless, innocent men both, to be brought out and hauled to some gallows he had caused to be erected on a spot visible to the Spaniards. They were both hanged, and Drake released a third and more fortunate prisoner to go and explain to the Spaniards why he had done it. Two prisoners a day would be executed, he told them, unless the murderer of the black messenger was surrendered or punished. It was enough, for the offender was hanged by his own countrymen. It may be that some of them were ashamed of what he had done, and one eye-witness gave out that Drake had hanged the friars because they had opposed the teachings of one of the English Lutheran parsons!

In handling his own men, Sir Francis appeared in a happier mood. He even found a solution for the Knollys problem, which had been left simmering all the way across the Atlantic. Now the unfortunate subject of the argument was pressing Drake to make a decision, and at one time the Bark Hawkins was being prepared to ship Knollys and his malcontents back home. But on 10 January the admiral attempted a reconciliation with his errant captain. Fenner was hosting a dinner, and Drake used the occasion to draw Knollys and Captain Winter into a private room, where he declared that if only Knollys would accept the oath of allegiance he would be used as well as any man – nay, better, for Drake would allow him to act as rear-admiral. This was a generous offer, and one Sir Francis must have found difficult to make, but it struck to the root of the problem by raising Knollys’s status in the fleet. Remarkably, the stupid man rejected it, and still insisted on returning on the Bark Hawkins as originally planned. It took several weeks for him reluctantly to accept the suggestion and bury the miserable squabble for the rest of the voyage.

By the end of January 1586 the ransom for Santo Domingo had been paid, and the English, much behind their schedule, were ready to leave. Behind was left a sorrowful sight, the humiliation of a proud city, the worst blow Philip had yet suffered in the New World. A third of the houses had been destroyed, along with the churches, monasteries, nunneries and the castle. The governor’s house had been stripped of anything valuable and the cathedral was an empty shell. The naval galley and twenty or so small barks had been burned, and a few captured ships had been taken away, to replace three discarded English vessels, the Hope, Benjamin and Scout. As the inhabitants drifted back to their broken homes in the smoking city there was much anguish and despair. Torrequemada bewailed that ‘this thing must have had Divine sanction, as punishment for the people’s sins.’ Another official informed Philip that ‘the destruction of this, Your Majesty’s city, and the evils which have befallen us, Your Majesty’s servants and vassals, cannot be recounted without tears.’ And yet another inhabitant put it more simply still. ‘Nothing remains,’ he said, ‘but life itself.’¹⁶

¹ Leicester to Burghley, 29 January, 1586, Butler, et. al., ed., Cal. State Papers Foreign, 20: 330–2. The principal documents dealing with this voyage are contained in Corbett, ed., Papers Relating to the Navy During the Spanish War; Keeler, ed., Sir Francis Drake’s West Indian Voyage; Wright, ed., Further English Voyages to Spanish America; and Palencia, ed., Discurso de el Capitan Francisco Draque (appendices).

³ Dispatches refer only incidentally to the Sidney affair. A full, but late and probably unreliable account is in Greville, Life of Sir Philip Sidney. See also Corbett, Drake and the Tudor Navy, 2: 16–21.

⁴ Journal of the Tiger, 17 September, 1585, Keeler, 73. Drake was considered to be both admiral and general of the expedition, but I have used the former term to avoid confusion.

⁶ In addition to the above sources, see Bermudez to Santa Cruz, 7 October, 1585, Brown, ed., Calendar of State Papers … in the Archives and Collections of Venice, 124–5.

⁷ The violence to property admitted, there are few grounds for charging Drake with injury to persons at this stage. The journal of the Primrose remarks that two prisoners were abused by ‘a certain kind of torment’ (Keeler, 188), but this is at least vague and possibly exaggerated. One of the prisoners, Octavius Toscano, left a deposition that suggests that he suffered nothing worse than being made to serve at the table.

¹¹ Ibid, 146. The account in the journal of the Leicester is the only detailed source for this affair.

¹² Alonso Rodriguez de Azebedo to Diego Fernandez de Quiñones, 22 January, 1586, Wright, 25–7.

¹³ Corbett’s view that Drake contacted the cimarrones of Santo Domingo, who finished off the watchmen by the Hayna so that Drake could land unopposed, is founded only upon an unsupported intelligence report and is likely incorrect (Corbett, Spanish War, 79–80).

¹⁶ Rodrigo Fernández de Ribera to the Crown, 30 June, 1586, Wright, 178–80; deposition, 20 February, 1586, Klarwill, ed., Fugger News-Letters, 1:89–93.