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Updated: May 24, 2025
Taken in flank by Carleill, and threatened in the rear by his second column under Powell, the chief of the staff, the infantry could make no real resistance; and so rapidly was the English advance pushed home that the struggling mass of friend and foe entered pell-mell through the open gates of the town.
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.
Threatened by Carleill from the heights above the valley where it lies, and from the sea by Drake, without a blow the town was abandoned to its fate. For ten days the island was scoured for plunder and provisions, and ere the month was out the anchorage was desolate and Santiago a heap of ashes.
Thus, unseen and unmolested, the troops were successfully landed, and then, with pious and cheery farewells to Carleill, Drake returned to the fleet to prepare the ground for the surprise. In the morning he anchored in the road, ran out his guns, and proceeded to threaten a landing at a point close to that side of the town upon which Carleill was stealthily approaching in two parallel columns.
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.
Meanwhile Frobisher advanced with the flotilla against the harbor fort, and as soon as Carleill was heard in contact with the enemy's pickets he opened fire. The boat-attack was repulsed indeed, it may only have been intended as what soldiers then called "a hot alarm" but Carleill was completely successful.
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.
Instead of being landed on the mainland, Carleill with eight companies was quietly slipped ashore in the Bocca Grande, with instructions to make his way diagonally through the woods that covered the spit till he reached the seashore, and then, instead of advancing on the front of the intrenchments, to wade along through the wash of the surf till he was within striking distance of the Spanish position.
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.
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.
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