Chronicles of America 

Sir Francis Drake in the Ports of Spain

For three years after Drake had been dubbed Sir Francis by the Queen he was the hero of every class of Englishmen but two: the extreme Roman Catholics, who wanted Mary Queen of Scots, and the merchants who were doing business with Portugal and Spain. The Marian opposition to the general policy of England persisted for a few years longer. But the merchants who were the inheritors of centuries of commercial intercourse with England's new enemies were soon to receive a shock that completely changed their minds. They were themselves one of the strongest factors that made for war in the knotty problem now to be solved at the cannon's mouth because English trade was seeking new outlets in every direction and was beating hard against every door that foreigners shut in its face. These merchants would not, however, support the war party till they were forced to, as they still hoped to gain by other means what only war could win.

The year that Drake came home (1580) Philip at last got hold of a sea-going fleet, the eleven big Portuguese galleons taken when Lisbon fell. With the Portuguese ships, sailors, and oversea possessions, with more galleons under construction at Santander in Spain, and with the galleons of the Indian Guard built by the great Menendez to protect New Spain: with all this performed or promised, Philip began to feel as if the hour was at hand when he could do to England what she had done to him.

In 1583 Santa Cruz, the best Spanish admiral since the death of Menendez, proposed to form the nucleus of the Great Armada out of the fleet with which he had just broken down the last vestige of Portuguese resistance in the Azores. From that day on, the idea was never dropped. At the same time Elizabeth discovered the Paris Plot between Mary and Philip and the Catholics of France, all of whom were bent on her destruction. England stood to arms. But false ideas of naval defence were uppermost in the Queen's Council. No attempt was made to strike a concentrated blow at the heart of the enemy's fleet in his own waters. Instead of this the English ships were carefully divided among the three squadrons meant to defend the approaches to England, Ireland, and Scotland, because, as the Queen-in-Council sagely remarked, who could be expected to know what the enemy's point of attack would be? The fact is that when wielding the forces of the fleet and army the Queen and most of her non-combatant councillors never quite reached that supreme point of view from which the greatest statesmen see exactly where civil control ends and civilian interference begins. Luckily for England, their mistakes were once more covered up by a turn of the international kaleidoscope.

No sooner had the immediate danger of a great combined attack on England passed away than Elizabeth returned to Drake's plan for a regular raid against New Spain, though it had to be one that was not designed to bring on war in Europe. Drake, who was a member of the Navy Board charged with the reorganization of the fleet, was to have command. The ships and men were ready. But the time had not yet come.

Next year (1584) Amadas and Barlow, Sir Walter Raleigh's two prospectors for the 'plantation' of Virginia, were being delighted with the summer lands and waters of what is now North Carolina. We shall soon hear more of Raleigh and his vision of the West. But at this time a good many important events were happening in Europe; and it is these that we must follow first.

William of Orange, the Washington of Holland, was assassinated at Philip's instigation, while plots to kill Elizabeth and place Mary on the throne began to multiply. The agents were executed, while a 'Bond of Association' was signed by all Elizabeth's chief supporters, binding them to hunt down and kill all who tried to kill her--a plain hint for Mary Queen of Scots to stop plotting or stand the consequences.

But the merchants trading with Spain and Portugal were more than ever for keeping on good terms with Philip because the failure of the Spanish harvest had induced him to offer them special protection and encouragement if they would supply his country's needs at once. Every available ton of shipping was accordingly taken up for Spain. The English merchant fleet went out, and big profits seemed assured. But presently the "Primrose", 'a tall ship of London,' came flying home to say that Philip had suddenly seized the merchandise, imprisoned the men, and taken the ships and guns for use with the Great Armada. That was the last straw. The peaceful traders now saw that they were wrong and that the fighting ones were right; and for the first time both could rejoice over the clever trick by which John Hawkins had got his own again from Philip. In 1571, three years after Don Martin's treachery at San Juan de Ulna, Hawkins, while commanding the Scilly Island squadron, led the Spanish ambassador to believe that he would go over to the Spanish cause in Ireland if his claims for damages were only paid in full and all his surviving men in Mexico were sent home. The cold and crafty Philip swallowed this tempting bait; sent the men home with Spanish dollars in their pockets, and paid Hawkins forty thousand pounds, the worth of about two million dollars now. Then Hawkins used the information he had picked up behind the Spanish scenes to unravel the Ridolfi Plot for putting Mary on the throne in 1572, the year of St. Bartholomew. No wonder Philip hated sea-dogs!

Things new and old having reached this pass, the whole of England, bar the Marians, were eager for the great 'Indies Voyage' of 1585. Londoners crowded down to Woolwich 'with great jolitie' to see off their own contingent on its way to join Drake's flag at Plymouth. Very probably Shakespeare went down too, for that famous London merchantman, the "Tiger", to which he twice alludes--once in "Macbeth" and once in "Twelfth Night"--was off with this contingent. Such a private fleet had never yet been seen: twenty-one ships, eight smart pinnaces, and twenty-three hundred men of every rank and rating. The Queen was principal shareholder and managing director. But, as usual in colonial attacks intended for disavowal if necessity arose, no prospectus or other document was published, nor were the shareholders of this joint-stock company known in any quite official way. It was the size of the fleet and the reputation of the officers that made it a national affair. Drake, now forty, was 'Admiral'; Frobisher, of North-West-Passage fame, was 'Vice'; Knollys, the Queen's own cousin, 'Rear.' Carleill, a famous general, commanded the troops and sailed in Shakespeare's "Tiger". Drake's old crew from the "Golden Hind" came forward to a man, among them Wright, 'that excellent mathematician and ingineer,' and big Tom Moone, the lion of all boarding-parties, each in command of a ship.

But Elizabeth was just then weaving the threads of an unusually intricate diplomatic pattern; so doubts and delays, orders and counter-orders vexed Drake to the last. Sir Philip Sidney, too, came down as a volunteer; which was another sore vexation, since his European fame would have made him practically joint commander of the fleet, although he was not a naval officer at all. But he had the good sense to go back; whereupon Drake, fearing further interruptions from the court, ordered everything to be tumbled into the nearest ships and hurried off to sea under a press of sail.

The first port of call was Vigo in the northwestern corner of Spain, where Drake's envoy told the astonished governor that Elizabeth wanted to know what Philip intended doing about embargoes now. If the governor wanted peace, he must listen to Drake's arguments; if war--well, Drake was ready to begin at once. A three-days' storm interrupted the proceedings; after which the English intercepted the fugitive townsfolk whose flight showed that the governor meant to make a stand, though he had said the embargo had been lifted and that all the English prisoners were at liberty to go. Some English sailors, however, were still being held; so Drake sent in an armed party and brought them off, with a good pile of reprisal booty too. Then he put to sea and made for the Spanish Main by way of the Portuguese African islands.

The plan of campaign drawn up for Burleigh's information still exists. It shows that Drake, the consummate raider, was also an admiral of the highest kind. The items, showing how long each part should take and what loot each place should yield, are exact and interesting. But it is in the relation of every part to every other part and to the whole that the original genius of the born commander shines forth in all its glory. After taking San Domingo he was to sack Margarita, La Hacha, and Santa Marta, razing their fortifications as he left. Cartagena and Nombre de Dios came next. Then Carleill was to raid Panama, with the help of the Maroons, while Drake himself was to raid the coast of Honduras. Finally, with reunited forces, he would take Havana and, if possible, hold it by leaving a sufficient garrison behind. Thus he would paralyze New Spain by destroying all the points of junction along its lines of communication just when Philip stood most in need of its help for completing the Great Armada.

But, like a mettlesome steeplechaser, Drake took a leap in his stride during the preliminary canter before the great race. The wind being foul for the Canaries, he went on to the Cape Verde archipelago and captured Santiago, which had been abandoned in terror on the approach of the English 'Dragon,' that sinister hero of Lope de Vega's epic onslaught "La Dragontea". As good luck would have it, Carleill marched in on the anniversary of the Queen's accession, the 17th of November. So there was a royal salute fired in Her Majesty's honor by land and sea. No treasure was found, French privateers had sacked the place three years before and had killed off everyone they caught; the Portuguese, therefore, were not going to wait to meet the English 'Dragon' too. The force that marched inland failed to unearth the governor. So San Domingo, Santiago, and Porto Pravda were all burnt to the ground before the fleet bore away for the West Indies.

San Domingo in Hispaniola (Hayti) was made in due course, but only after a virulent epidemic had seriously thinned the ranks. San Domingo was the oldest town in New Spain and was strongly garrisoned and fortified. But Carleill's soldiers carried all before them. Drake battered down the seaward walls. The Spaniards abandoned the citadel at night, and the English took the whole place as a New Year's gift for 1586. But again there was no treasure. The Spaniards had killed off the Caribs in war or in the mines, so that nothing was now dug out. Moreover the citizens were quite on their guard against adventurers and ready to hide what they had in the most inaccessible places. Drake then put the town up to ransom and sent out his own Maroon boy servant to bring in the message from the Spanish officer proposing terms. This Spaniard, hating all Maroons, ran his lance through the boy and cantered away. The boy came back with the last ounce of his strength and fell dead at Drake's feet. Drake sent to say he would hang two Spaniards every day if the murderer was not hanged by his own compatriots. As no one came he began with two friars. Then the Spaniards brought in the offender and hanged him in the presence of both armies.

That episode cleared the air; and an interchange of courtesies and hospitalities immediately followed. But no business was done. Drake therefore began to burn the town bit by bit till twenty-five thousand ducats were paid. It was very little for the capital. But the men picked up a good deal of loot in the process and vented their ultra-Protestant zeal on all the 'graven images' that were not worth keeping for sale. On the whole the English were well satisfied. They had taken all the Spanish ships and armament they wanted, destroyed the rest, liberated over a hundred brawny galley-slaves--some Turks among them--all anxious for revenge, and had struck a blow at Spanish prestige which echoed back to Europe. Spain never hid her light under a bushel; and here, in the Governor's Palace, was a huge escutcheon with a horse standing on the earth and pawing at the sky. The motto blazoned on it was to the effect that the earth itself was not enough for Spain--"Non sufficit orbis." Drake's humor was greatly tickled, and he and his officers kept asking the Spaniards to translate the motto again and again.

Delays and tempestuous head winds induced Drake to let intermediate points alone and make straight for Cartagena on the South American mainland. Cartagena had been warned and was on the alert. It was strong by both nature and art. The garrison was good of its kind, though the Spaniards' custom of fighting in quilted jackets instead of armor put them at a disadvantage. This custom was due to the heat and to the fact that the jackets were proof against the native arrows.

There was an outer and an inner harbor, with such an intricate and well-defended passage that no one thought Drake would dare go in. But he did. Frobisher had failed to catch a pilot. But Drake did the trick without one, to the utter dismay of the Spaniards. After some more very clever manoeuvres, to distract the enemy's attention from the real point of attack, Carleill and the soldiers landed under cover of the dark and came upon the town where they were least expected, by wading waist-deep through the water just out of sight of the Spanish gunners. The entrenchments did not bar the way in this unexpected quarter. But wine casks full of rammed earth had been hurriedly piled there in case the mad English should make the attempt. Carleill gave the signal. Goring's musketeers sprang forward and fired into the Spaniards' faces. Then Sampson's pikemen charged through and a desperate hand-to-hand fight ensued. Finally the Spaniards broke after Carleill had killed their standard-bearer and Goring had wounded and taken their commander. The enemies ran pell-mell through the town together till the English reformed in the Plaza. Next day Drake moved in to attack the harbor fort; whereupon it was abandoned and the whole place fell.

But again there was a dearth of booty. The Spaniards were getting shy of keeping too many valuables where they could be taken. So negotiations, emphasized by piecemeal destruction, went on till sickness and the lateness of the season put the English in a sorry fix. The sack of the city had yielded much less than that of San Domingo; and the men, who were all volunteers, to be paid out of plunder, began to grumble at their ill-success. Many had been wounded, several killed--big, faithful Tom Moone among them. A hundred died. More were ill. Two councils of war were held, one naval, the other military. The military officers agreed to give up all their own shares to the men. But the naval officers, who were poorer and who were also responsible for the expenses of their vessels, could not concur. Finally 110,000 ducats (equivalent in purchasing power to nearly three millions of dollars) were accepted.

It was now impossible to complete the programme or even to take Havana, in view of the renewed sickness, the losses, and the advance of the season. A further disappointment was experienced when Drake just missed the treasure fleet by only half a day, though through no fault of his own. Then, with constantly diminishing numbers of effective men, the course was shaped for the Spanish 'plantation' of St. Augustine in Florida. This place was utterly destroyed and some guns and money were taken from it. Then the fleet stood north again till, on the 9th of June, it found Raleigh's colony of Roanoke.

Ralph Lane, the governor, was in his fort on the island ready to brave it out. Drake offered a free passage home to all the colonists. But Lane preferred staying and going on with his surveys and 'plantation.' Drake then filled up a store ship to leave behind with Lane. But a terrific three-day storm wrecked the store ship and damped the colonists' enthusiasm so much that they persuaded Lane to change his mind. The colonists embarked and the fleet then bore away for home. Though balked of much it had expected in the way of booty, reduced in strength by losses, and therefore unable to garrison any strategic point which would threaten the life of New Spain, its purely naval work was a true and glorious success. When he arrived at Plymouth, Drake wrote immediately to Burleigh: 'My very good Lord, there is now a very great gap opened, very little to the liking of the King of Spain.'

This 'very great gap' on the American side of the Atlantic was soon to be matched by the still greater gap Drake was to make on the European side by destroying the Spanish Armada and thus securing that mightiest of ocean highways through which the hosts of emigration afterwards poured into a land endowed with the goodly heritage of English liberty and the English tongue.


The year of Drake's return (1586) was no less troublous than its immediate predecessors. The discovery of the Babington Plot to assassinate Elizabeth and to place Mary on the throne, supported by Scotland, France, and Spain, proved Mary's complicity, produced an actual threat of war from France, and made the Pope and Philip gnash their teeth with rage. The Roman Catholic allied powers had no sufficient navy, and Philip's credit was at its lowest ebb after Drake's devastating raid. The English were exultant, east and west; for the "True Report of a Worthie Fight performed in the voiage from Turkie by Five Shippes of London against 11 gallies and two frigats of the King of Spain at Pantalarea, within the Straits" [of Gibraltar] "Anno 1586" was going the rounds and running a close second to Drake's West India achievement. The ignorant and thoughtless, both then and since, mistook this fight, and another like it in 1590, to mean that English merchantmen could beat off Spanish men-of-war. Nothing of the kind: the English Levanters were heavily armed and admirably manned by well-trained fighting crews; and what these actions really proved, if proof was necessary, was that galleys were no match for broadsides from the proper kind of sailing ships.

Turkey came into the problems of 1586 in more than name, for there was a vast diplomatic scheme on foot to unite the Turks with such Portuguese as would support Antonio, the pretender to the throne of Portugal, and the rebellious Dutch against Spain, Catholic France, and Mary Stuart's Scotland. Leicester was in the Netherlands with an English army, fighting indecisively, losing Sir Philip Sidney and angering Elizabeth by accepting the governor-generalship without her leave and against her diplomacy, which, now as ever, was opposed to any definite avowal that could possibly be helped.

Meanwhile the Great Armada was working up its strength, and Drake was commissioned to weaken it as much as possible. But, on the 8th of February, 1587, before he could sail, Mary was at last beheaded, and Elizabeth was once more entering on a tricky course of tortuous diplomacy too long by half to follow here. As the great crisis approached, it had become clearer and clearer that it was a case of kill or be killed between Elizabeth and Mary, and that England could not afford to leave Marian enemies in the rear when there might be a vast Catholic alliance in the front. But, as a sovereign, Elizabeth disliked the execution of any crowned head; as a wily woman she wanted to make the most of both sides; and as a diplomatist she would not have open war and direct operations going down to the root of the evil if devious ways would do.

So the peace party of the Council prevailed again, and Drake's orders were changed. He had been going as a lion. The peace party now tried to send him as a fox. But he stretched his instructions to their utmost limits and even defied the custom of the service by holding no council of war when deciding to swoop on Cadiz.

As they entered the harbor, the English saw sixty ships engaged in preparations for the Great Armada. Many had no sails--to keep the crews from deserting. Others were waiting for their guns to come from Italy. Ten galleys rowed out to protect them. The weather and surroundings were perfect for these galleys. But as they came end-on in line-abreast Drake crossed their T in line-ahead with the shattering broadsides of four Queen's ships which soon sent them flying. Each galley was the upright of the T, each English sailing ship the corresponding crosspiece. Then Drake attacked the shipping and wrecked it right and left. Next morning he led the pinnaces and boats into the inner harbor, where they cut out the big galleon belonging to Santa Cruz himself, the Spanish commander-in-chief. Then the galleys got their chance again--an absolutely perfect chance, because Drake's fleet was becalmed at the very worst possible place for sailing ships and the very best possible place for the well-oared galleys. But even under these extraordinary circumstances the ships smashed the galleys up with broadside fire and sent them back to cover. Then the Spaniards towed some fire-ships out. But the English rowed for them, threw grappling irons into them, and gave them a turn that took them clear. Then, for the last time, the galleys came on, as bravely but as uselessly as ever. When Drake sailed away he left the shipping of Cadiz completely out of action for months to come, though fifteen sail escaped destruction in the inner harbor. His own losses were quite insignificant.

The next objective was Cape St. Vincent, so famous through centuries of naval history because it is the great strategic salient thrust out into the Atlantic from the southwest corner of Europe, and thus commands the flank approaches to and from the Mediterranean, to and from the coast of Africa, and, in those days, the route to and from New Spain by way of the Azores. Here Drake had trouble with Borough, his second-in-command, a friend of cautious Burleigh and a man hide-bound in the warfare of the past--a sort of English Don. Borough objected to Drake's taking decisive action without the vote of a council of war. Remembering the terrors of Italian textbooks, he had continued to regard the galleys with much respect in the harbor of Cadiz even after Drake had broken them with ease. Finally, still clinging to the old ways of mere raids and reprisals, he stood aghast at the idea of seizing Cape St. Vincent and making it a base of operations. Drake promptly put him under arrest.

Sagres Castle, commanding the roadstead of Cape St. Vincent, was extraordinarily strong. The cliffs, on which it occupied about a hundred acres, rose sheer two hundred feet all round except at a narrow and well defended neck only two hundred yards across. Drake led the stormers himself. While half his eight hundred men kept up a continuous fire against every Spaniard on the wall the other half rushed piles of faggots in against the oak and iron gate. Drake was foremost in this work, carrying faggots himself and applying the first match. For two hours the fight went on; when suddenly the Spaniards sounded a parley. Their commanding officer had been killed and the woodwork of the gate had taken fire. In those days a garrison that would not surrender was put to the sword when captured; so these Spaniards may well be excused. Drake willingly granted them the honors of war; and so, even to his own surprise, the castle fell without another blow. The minor forts near by at once surrendered and were destroyed, while the guns of Sagres were thrown over the cliffs and picked up by the men below. The whole neighboring coast was then swept clear of the fishing fleet which was the main source of supply used for the Great Armada.

The next objective was Lisbon, the headquarters of the Great Armada, one of the finest harbors in the world, and then the best fortified of all. Taking it was, of course, out of the question without a much larger fleet accompanied by an overwhelming army. But Drake reconnoitered to good effect, learnt wrinkles that saved him from disaster two years later, and retired after assuring himself that an Armada which could not fight him then could never get to England during the same season.

Ship fevers and all the other epidemics that dogged the old sailing fleets and scourged them like the plague never waited long. Drake was soon short-handed. To add to his troubles, Borough sailed away for home; whereupon Drake tried him and his officers by court-martial and condemned them all to death. This penalty was never carried out, for reasons we shall soon understand. Since no reinforcements came from home, Cape St. Vincent could not be held any longer. There was, however, one more stroke to make. The great East-India Spanish treasure ship was coming home; and Drake made up his mind to have her.

Off the Azores he met her coming towards him and dipping her colors again and again to ask him who he was. 'But we would put out no flag till we were within shot of her, when we hanged out flags, streamers, and pendants. Which done, we hailed her with cannon-shot; and having shot her through divers times, she shot at us. Then we began to ply her hotly, our fly boat [lightly armed supply vessel of comparatively small size] and one of our pinnaces lying athwart her hawse [across her bows] at whom she shot and threw fire-works [incendiary missiles] but did them no hurt, in that her ordnance lay so high over them. Then she, seeing us ready to lay her aboard [range up alongside], all of our ships plying her so hotly, and resolutely determined to make short work of her, they yielded to us.' The Spaniards fought bravely, as they generally did. But they were only naval amateurs compared with the trained professional sea-dogs.

The voyage was now 'made' in the old sense of that term; for this prize was 'the greatest ship in all Portugal, richly laden, to our Happy Joy.' The relative values, then and now, are impossible to fix, because not only was one dollar the equivalent in most ways of ten dollars now but, in view of the smaller material scale on which men's lives were lived, these ten dollars might themselves be multiplied by ten, or more, without producing the same effect as the multiplied sum would now produce on international affairs. Suffice it to say that the ship was worth nearly five million dollars of actual cash, and ten, twenty, thirty, or many more millions if present sums of money are to be considered relatively to the national incomes of those poorer days.

But better than spices, jewels, and gold were the secret documents which revealed the dazzling profits of the new East-India trade by sea. From that time on for the next twelve years the London merchants and their friends at court worked steadily for official sanction in this most promising direction. At last, on the 31st of December, 1600, the documents captured by Drake produced their result, and the East-India Company, by far the greatest corporation of its kind the world has ever seen, was granted a royal charter for exclusive trade. Drake may therefore be said not only to have set the course for the United States but to have actually discovered the route leading to the Empire of India, now peopled by three hundred million subjects of the British Crown.

So ended the famous campaign of 1587, popularly known as the singeing of King Philip's beard. Beyond a doubt it was the most consummate work of naval strategy which, up to that time, all history records.

Back to: English Exploration of America