This section is from the book "Elizabethan Sea Dogs", by Gerhard R. Lomer and Charles W. Jefferys. Also available from Amazon: Elizabethan Sea Dogs.
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 threerdays' 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 oh 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 Praya 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. Aiter 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.
 
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