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Authors: Susan Ronald

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Twelve days later, the high sheriff met Drake to negotiate their release. Drake asked for a million ducats (the amount at which he had originally valued the plunder). The
alcalde
muttered that such a sum was impossible, that there wasn’t that much money in the whole of his jurisdiction. So Drake told him that they would be compelled to burn the town down, building by building, until his demands were met. At this point, the king’s factor, García Fernández de Torrequemada, took over the negotiations while Santo Domingo burned. In the end, Drake was forced to compromise on the not so paltry figure of 25,000 ducats, raising their total takings to £11,275 ($3.27 million or £1.77 million today). Nonetheless, the figure was still disappointing to Sir Francis and his men.

Afterward, Fernández de Torrequemada wrote to Philip, “Drake is a man of medium stature, blond, 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.”
8
Considering that Drake had ordered the destruction
of over a third of Santo Domingo—from the lowliest houses to its churches, monastery, and castle—this was high praise indeed. While Torrequemada watched the English fleet weigh anchor leaving behind the smoldering ruin of the New World’s oldest settlement, he couldn’t help but wonder aloud that “this thing must have had Divine sanction as punishment for the people’s sins.”
9

 

While the fall of Santo Domingo sent an aftershock through the Caribbean and beyond, Grenville was counting his cash back in London. After he had sailed from Roanoke on August 25, 1585, he had had the good fortune to fall in behind the flota and give chase. Of the thirty-three ships that had left Havana in July, only the 300-ton unarmed
Santa Maria
straggled behind the rest, squatting heavily on the rolling sea cradling treasure in her hold. The English pirate adventurers had long ago uncovered the unmistakable and ungainly gait of a ship laden with treasure, and gave chase. When the
Tiger
overcame her, the
Santa Maria
had no alternative but to surrender to the faster, sleeker vessel bristling with firepower, flying the flag of St. George, and the queen’s colors.

Once aboard his Spanish prize, Grenville could hardly believe his good luck. He held up the passengers at gunpoint and ordered them to pass across their valuables. The ship’s manifest confirmed that a rich cargo of gold, silver, and pearls, calf hides, sugar, ginger, and cochineal was stowed aboard. In all, it was valued at 120,000 ducats—roughly £30,000, or $8.70 million or £4.7 million today. Grenville ordered the treasure to be removed to the
Tiger
, while he captained the prize back to Plymouth. Not only was the ship worth a great deal more, but there was also the good possibility of ransoming his hostages. The first voyage to colonize North America had been made, not by a “western planting” but by plunder. Grenville knew, as did any good sea captain in Elizabeth’s reign, that his duty was not only to accompany the colonists to safety on foreign shores, but also to ensure the financial aspects—profit to the joint stockholders—remained uppermost in their minds. And plunder was the surest way of making exploration pay quickly. On their return to Plymouth on October 18, 1585—one month after Drake’s fleet had sailed—Elizabeth was said to have
been so delighted with the quality of the pearls that she kept a whole cabinet filled with them for her own use.
10

In the closing months of 1585, while Sir Richard Grenville basked in the glory of his haul in the comfort of an excited London, Ralph Lane and his 107 settlers were toiling to try to make their colony work. Lane, an exceptionally strict disciplinarian who had recommended keelhauling as punishment on the outbound voyage, was not above meting out the harshest sentences imaginable on land to keep his “riff raff” in check.
11
There were carpenters, metallurgists like the German Jewish expert Joachim Ganz, former soldiers from Ireland, “drones and grumblers” masquerading as gentlemen, and a few who knew how to till the soil, though they weren’t specialist gardeners or farmers. Lane wrote that most “had little or no care for any other thing but to pamper their bellies,” then adding, “Because there were not to be found any English cities, nor such fair houses, nor at their own wish any of their old accustomed dainty food, nor any soft beds of down or feathers, the country was to them miserable.”

Of his second in command, Philip Amadas, Lane extolled rare praise when he said “he was the gentleman that never spared labour or peril either by land or water, fair weather or foul, to perform any service committed unto him.” Thomas Hariot had accompanied Lane as the chief mathematician, but his observations pale into insignificance (as do Lane’s) when compared to the amazing body of drawings provided to posterity by the expedition’s accredited artist, John White. White had already made his name in England for his stunning portraits of the Inuit tribesmen on Baffin Island during Frobisher’s 1577 voyage, and his drawings in Virginia remain our most poignant reminders today of that ill-fated colony.
12

The critical task ahead, aside from staying alive, was to find a better natural harbor than the one Roanoke afforded. Their “scouts” Manteo and Wanchese suggested exploring to the north, where they believed the ideal harbor existed. Lane and a small party of settlers discovered Chesapeake Bay and spent part of their first American winter inland there, making friends with the Chesapeake tribe. Lane reported that “a good harbor being found to the northward…you shall clear yourself from all those dangers and broad shallow sounds…and gain within four days travel into the heart of the Main
200 miles at the least…the territory and soil of the Chesepians was for pleasantness of seat, for temperature of climate, of fertility of soil and for the commodity of the sea…not to be excelled by any other whatsoever.”
13

In the spring, Lane took another expedition to the west, exploring the Albemarle Sound. From there, they headed north again, this time up the Chowan River, where they met the Chowan “king,” who showed them samples of his “wassador”—a metal deemed by Lane to be copper, or perhaps a different quality of gold. The Chowan chief also told Lane that there were pearls to be had in plentiful supply at the Chesapeake Bay. Lane did not question the Native American “king” and informed his settlers that their firm intention should be to remove themselves to the better harbor at Chesapeake, as soon as relief finally arrived from England. “The discovery of a good mine,” Lane remarked, “by the goodness of God, or a passage to the South Sea, or some way to it, and nothing else can bring this country in request to be inhabited by our nation.”
14
But he could do nothing until his English support arrived. On more than one occasion, Lane must have asked himself, where in the blazes was their relief from England?

 

That was the spring of 1586, when Drake’s name rang throughout Spanish America and Catholic Europe like a death knell. In England, the Low Countries, and other Protestant nation-states, it brought cascades of joy. Rumors, most based on the incredible truth, abounded with Drake said to have liberated twelve thousand slaves on Hispaniola. Some said he had been defeated at Havana, others that he had taken the flagship of the Peruvian flota and 300,000 ducats booty. But these rumors were at variance with the truth.

The Spanish colonies in the New World were thrown into terror, confusion, and disarray by the news of Drake’s fleet and the ransoming of Santo Domingo. While the cash prize for the city was miniscule to Spaniard and Englishman alike, the catastrophic blow to Spain’s prestige was irrecoverable. Though ill-prepared to mount a defense against the faster, more weatherly, more heavily armed, and more brazen English fleet, they had little choice. Either defend Spanish America, or lose it entirely. Their greatest dilemma was, however, to answer the burning question: Where would Drake strike next?

During the night of February 9–10, Sir Francis landed Carleill with around a thousand men near the fort of La Caleta, where Cartagena’s battery guns were located. Carleill’s men had to pick their way through the darkness, carefully avoiding the poisoned stakes driven into the path by the Indians. The Caleta’s defenses were not strong, but they could inflict serious damage on the English fleet if Carleill were unable to overcome them. Unlike sleepy Santo Domingo, Cartagena—as all of Spain’s important cities and towns in the New World now—was on high alert. While Carleill and his men advanced, the three hundred Spanish soldiers and two hundred Indians tried to ambush the advancing English but, when they failed, scurried for cover. Around an hour before dawn, Carleill and his men had snaked their way within reach of the Caleta. The attack order was given, and as the English sprang forth from the brush on the far side of the fort from the harbor, the Spaniards opened fire roaring, “Come on, heretic dogs!” Galleys in the port fired high, but as Carleill was out of range, their shot was useless. Also on the far side of the fort, the wall had been ravaged by poor maintenance and time, and all the English had to do was to kick in the flimsy thirty-foot-wide wine-butt barricade that had been erected in haste to keep them out. After the briefest pike battle, most of the Spaniards fled to the town, hotly pursued by the English.
15
In the meantime, two galleys ran aground as they attempted to escape, and the order was given by their admiral to destroy them at once so Drake could not benefit from the disaster. But Drake was never one to come up empty-handed. He had already seized the
Santa Clara
and the
Napolitana
, as well as the few remaining vessels in harbor.
16
And so, a day later, Sir Francis Drake was master of Cartagena.

Drake turned his attention to the business of administering his prize while also trying to stave off the unwelcome reappearance of the “fever” in his fleet. Fresh wells were dug for clean water; “Frenchmen, Turks and Negroes”—to a man Spanish prisoners—were released and ordered by Drake to be treated with the greatest civility. The Turks were so thankful that more than one hundred of them begged to accompany Drake’s fleet back to England. Sir Francis, of course, complied.

The business of ransom was undertaken with decorum on both sides. Sir Francis demanded 5,000 ducats ransom for Alonso Bravo
to cover the preservation of his home and neighborhood ($362,138 or £195,750 today). When he heard that Bravo’s wife was terminally ill, Drake agreed that the Spaniard could return home to keep her company for as long as necessary and until the agreed ransom was paid. When his wife, Elvira, died, Drake and his men attended her funeral, and provided the pomp and ceremony at which the English so excel, with their muffled drums, flags drawn up high, and a proper military volley shot off as befitted a brave soldier’s wife. As he had demanded a further 3,000 ducats for the priory where Elvira was buried, in an incongruous act of generosity, Sir Francis reduced the demand to a nominal 600 ducats, and a promise to Bravo that no one would disturb Elvira’s final resting place.

As negotiations progressed for the release of Cartagena, Drake’s initial demand for 400,000 ducats ($28.97 million or £15.66 million today) was whittled down. After 248 homes were destroyed by arson, a ransom of 107,000 ducats was finally secured in early March 1586. This brought the total yield for Cartagena to 113,000 gold ducats ($32.75 million or £17.7 million today), including the ransom paid by Bravo, the priory, and another small estate. But this small gain was offset by great personal loss. Half of the men who had survived the voyage of circumnavigation with him had lost their lives at Cartagena. Men like Thomas Moone and John Varney who had been with him from the beginning, had fallen. A hundred more men had died of the “fever,” including George Fortescue. Only seven hundred men remained fit for service—an attrition of sixteen hundred men from the original complement. Even Drake had to admit it was a grossly inadequate force to attack Havana. Notwithstanding this change in plan, there was no time to linger. Drake knew he was late in supporting Raleigh’s colony, and since the pickings were hopelessly poorer in the West Indies than anticipated, he did not want to fail in that important task as well.

At Cuba, they dug wells for fresh water, with Sir Francis mucking in with his sailors “up to his armpits” carrying the barrels of clean water aboard ship. Once replenished, the fleet sailed along the east coast of Florida to St. Augustine, Spain’s oldest city in Florida. Sir Francis called a “war council,” and Carleill and Frobisher agreed that the Spanish watchtower there posed a severe threat to Raleigh’s
settlement. The next day, after a few bullets were fired (that hit nothing) Sir Francis and his men took the town. To their delight, the governor had deserted so quickly that he fled without the £2,000 worth of money brought to the fort for safekeeping ($579,420 or £313,200 today). By May 29, two days after their siege, the town and fort were utterly destroyed.

 

Though Lane had no idea where Drake was—or even if it was Drake who had been still designated to come—and Drake was uncertain where to find Roanoke since Grenville hadn’t returned before Drake had left (thanks to the Philip Sidney incident), Sir Francis supposed that the colony lay at about 36
o
north. Amazingly he found Roanoke on June 9, and immediately saw that it didn’t offer any safe anchorage within the Outer Banks. Drake and a party of his men rowed ashore, to Lane’s immense relief. Relations between the Native Americans and the inept, unskilled settlers had deteriorated dramatically over the issue of the Englishmen badgering the natives for both food and water. Grenville had failed to return with fresh provisions at Easter, and now the natives were literally starving them out. Sir Francis offered that all of the settlers were welcome to return to England with the fleet, but Lane demurred. He wanted to stay. So Drake offered him the
Francis
and some small boats and food for four months and a hundred men to navigate the ships. Lane agreed to the second proposal and preparations began at once. But a huge June thunderstorm bubbled up and raged on for three solid days, driving the
Francis
, the
Sea Dragon
, the
White Lion
, and the
Talbot
out to sea.

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