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From Contemporary Narratives and Letters
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Sir Francis Drake
Sir Francis Drake, from the Trinity House [London] portrait of the preeminent Elizabethan seadog who commanded the expedition of 1585—86 against the Spanish West Indies.


The riches of the Americas made Spain the foremost power in Europe. This wealth, so tantalizingly long in transporting from New World to Old, also made her a target for freebooters. Spain's navigation secrets were jealously guarded, but men contrived to learn them in the dangerous and profitable school of piracy.

For a time, after the destruction of the French, so vividly described in part above, Spain had no formidable contestant for the "continent" of Florida. France was involved in civil wars. The Hollanders were struggling under a Spanish yoke. The English, their star in the ascendant, were just beginning to learn how to colonize. In fact, Sir Francis Drake, after the raid on St. Augustine described below, found Sir Walter Raleigh's first group of Roanoke Island colonists in straitened circumstances and took them back to England. The 15 men left on Roanoke Island by Grenville that same year to hold the country for England were but a token. Elizabeth, while encouraging commerce, exploration, raids on the Spanish Main, and even the colonizing projects of Raleigh, was husbanding her strength for the coming battle with Spain near at home.

Much of the piratical activity in the western hemisphere was highly organized, a clear reflection of European disturbances. For example, the depredations of Drake in 1585—1586 were intended by Elizabeth to be acts of reprisal for injuries received at the hands of the Spaniards, but were also expected to divert King Philip's attention from war in the Netherlands. The expedition may be thought of as an extreme form of diplomatic pressure exerted by the English at a time when they were drifting toward armed conflict with Spain. Drake commanded a fleet of about 25 ships and 2,300 men. His most important actions were against Santo Domingo and Cartagena; from both of those towns he wrung fat ransoms. He was returning to England when his lookout sighted the coastal watchtower of the St. Augustine settlement. About 150 soldiers constituted the bulk of the town's population. In the action that followed, both the weakness of the struggling colony and the formidable character of the English opponent came into clear relief. It was a foreshadowing of the Anglo-Spanish contest for naval power and colonial empire which was to come and which was to be signalized by the defeat of the "Invincible Armada" two years later.

Thomas Cates, a member of Drake's expedition, relates the story of the sack of St. Augustine as follows.

After three days spent in watering our Ships, wee departed now the second time from this Cape of S. Anthony [Cuba] the thirteenth of May [1586], and proceeding about the Cape of Florida, wee neuer touched any where; but coasting alongst Florida, and keeping the shore still in sight, the 28 of May early in the morning wee descried on the shore a place built like a Beacon, which was in deede a scaffold vpon foure long mastes raised on ende, for men to discouer to the seaward, being in the latitude of thirtie degrees, or very neere therevnto. Our Pinnesses manned, and comming to the shore, wee marched vp alongst the riuer side, to see what place the enemie held there: for none amongst vs had any knowledge thereof at all.

Here the Generall [Drake] tooke occasion to march with the companies himselfe in person, the Lieutenant generall [Christopher Carleill] hauing the Vantguard; and going a mile vp or somewhat more by the riuer side, we might discerne on the other side of the riuer ouer against vs, a Fort which newly had bene built by the Spaniards: and some mile or thereabout aboue the Fort was a little Towne or Village without walles, built of woodden houses, as the Plot [Plan] doeth plainely shew. Wee forthwith prepared to haue ordinance for the batterie; and one peece was a little before the Euening planted, and the first shot being made by the Lieutenant generall himselfe at their Ensigne, strake through the Ensigne, as wee afterwards vnderstood by a French man, which came vnto vs from them. One shot more was then made, which strake the foote of the Fort wall, which was all massiue timber of great trees like Mastes. The Lieutenant generall was determined to passe the riuer this night with 4. companies, and there to lodge himselfe intrenched as neare the Fort, as that he might play with his muskets and smallest shot vpon any that should appeare, and so afterwards to bring and plant the batterie with him: but the help of Mariners for that sudden to make trenches could not be had, which was the cause that this determination was remitted vntill the next night.

In the night the Lieutenant generall tooke a little rowing Skiffe, and halfe a dozen well armed, as Captaine Morgan, and Captaine Sampson, with some others besides the rowers, & went to view what guard the enemie kept, as also to take knowledge of the ground. And albeit he went as couertly as might be, yet the enemie taking ye Alarme, grew feareful that the whole force was approaching to the assault, and therefore with all speede abandoned the place after the shooting of some of their peeces. They thus gone, and hee being returned vnto vs againe, but nothing knowing of their flight from their Fort, forthwith came a French man being a Phipher (who had bene prisoner with them) in a little boate, playing on his Phiph the tune of the Prince of Orenge his song; and being called vnto by the guard, he tolde them before he put foote out of the boate, what he was himselfe, and how the Spaniards were gone from the Fort, offering either to remaine in hands there, or els to returne to the place with them that would goe.

Vpon this intelligence, the Generall, the Lieutenent generall, with some of the Captaines in one Skiffe, and the Vice-admirall with some others in his Skiffe, and two or three Pinnesses furnished of souldiers with them, put presently ouer towards the Fort, giuing order for the rest of the Pinnesses to follow. And in our Approch, some of the enemie bolder then the rest, hauing stayed behinde their company, shot off two peeces of ordinance at vs: but on shore wee went, and entred the place without finding any man there. When the day appeared, we found it built all of timber, the walles being none other but whole Mastes or bodies of trees set vpright and close together in maner of a pale, without any ditch as yet made, but wholy intended with some more time; for they had not as yet finished al their worke, hauing begunne the same some three or foure moneths before: so as, to say the trueth, they had no reason to keepe it, being subiect both to fire, and easie assault.

The platforme whereon the ordinance lay, was whole bodies of long pine trees, whereof there is great plentie, layd a crosse one on another, and some little earth amongst. There were in it thirteene or fourteene great peeces of Brasse ordinance, and a chest vnbroken vp, hauing in it the value of some two thousand pounds sterling by estimation of the kings treasure, to pay the souldiers of that place, who were a hundred and fiftie men.

The Fort thus wonne, which they called S. Iohn's Fort, and the day opened, wee assayed to goe to the towne, but could not by reason of some riuers and broken ground which was betweene the two places: and therefore being enforced to imbarke againe into our Pinnesses, wee went thither vpon the great maine river, which is called as also the Towne, by the name of S. Augustin.

At our approching to land, there were some that began to shew themselues, and to bestow some few shot vpon vs, but presently withdrew themselues. And in their running thus away, the Sergeant Maior [Capt. Anthony Powel] finding one of their horses ready sadled and brideled, tooke the same to follow the chase; and so ouergoing all his company, was (by one layd behind a bush) shotte through the head: and falling downe there with, was by the same and two or three more, stabbed in three or foure places of his body with swords and daggers, before any could come neere to his rescue. His death was much lamented, being in very deede an honest wise Gentleman, and a souldier of good experience, and of as great courage as any man might be.

In this place called S. Augustin, we vnderstood the king did keepe, as is before said, one hundred and fiftie souldiers, and at another place some dozen leagues beyond to the Northwards, called S. Helena, he did likewise keepe an hundred and fiftie more, seruing there for no other purpose, then to keepe all other nations from inhabiting any part of all that coast; the gouernment whereof was committed to one Pedro Melendez Marquesse, nephew to that Melendez the Admiral, who had ouerthrowen Master Iohn Hawkins in the bay of Mexico some seuenteen or eighteene yeeres agoe. This Gouernour had charge of both places, but was at this time in this place, and one of the first that left the same.

Cates' Account of Drake's Raid on St. Augustine, 1586.


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