Sir Francis Drake Captures Santo Domingo

In boats and pinnaces the troops were being rapidly embarked, and soon Drake in person was piloting the flotilla for the surf-beaten shore.

Continuing Drake Captures Cartegena; Raids Cadiz,
our selection from Sir Francis Drake by Julian Corbett published in 1890. The selection is presented in eight easy 5 minute installments.  For works benefiting from the latest research see the “More information” section at the bottom of these pages.

Previously in Drake Captures Cartegena; Raids Cadiz.

Time: 1585
Place: Santo Domingo

Five years ago at Santiago, the chief town of the Cape Verde Islands, young William Hawkins, a personal adherent of Drake’s, had been made the victim of some such treachery as his father and captain had suffered together at Vera Cruz. From that hour it was doomed. In the middle of November the fleet arrived in the road and the troops landed. 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.

Drake’s vengeance was complete, and, exulting like Gideon in the devastation that marked his course, he led his ships across the Atlantic. Is there a moment in history more tragic than that? For the first time since the ages began, a hostile fleet was passing the ocean — the pioneer of how many more that have gone and are yet to go — the forerunner of how much glory and shame and misery! What wonder if the curse of God seemed upon it? Hardly had it lost sight of land when it was stricken with sickness. In a few days some three hundred men were dead, and numbers of others prostrate and useless; but in unshaken faith, and with reverent wonder at the inscrutable will of Heaven, Drake never flinched or paused. His only thought was how to check the evil. At Dominica he got fresh provisions from the natives, and refreshed his sick with a few days on shore. At St. Christopher he again halted to spend Christmas and elaborate the details of his next move.

The point where Philip was now to feel the weight of his arm was the fair city of Santo Domingo in Hispanola. It was by far the most serious operation Drake had yet undertaken. Hitherto his exploits had been against places that were little more than struggling settlements, but Santo Domingo was indeed a city, stone-built and walled, and flanked with formidable batteries. It was held by a powerful garrison, as Drake learned from a captured frigate, and a naval force had been concentrated in the harbor for its defense. As the oldest town in the Indies, its renown had hitherto secured it from attack, and in Spain it was held the queen city of the colonial empire. The moral effect of its capture would be profound, and, besides, from Virginia the governor of Raleigh’s new colony had sent home a fabulous report of its wealth. Drake was fully alive to the gravity of the task before him. His dispositions had never been so elaborate, and they evince at least a touch of that military genius which the strategists of the next century denied him. While the sick were recruiting he sent forward a squadron to reconnoiter, and, if possible, to open communications with the maroons who infested the hills. For three days the garrison was thus exhausted with constant alarms, and then on January 1, 1586, the whole fleet appeared in the bay.

Night fell, and, as darkness closed the eyes of the harassed garrison, with the fleet all was activity. In boats and pinnaces the troops were being rapidly embarked, and soon Drake in person was piloting the flotilla for the surf-beaten shore. At a point within the bay, but some ten miles from the town, a practicable landing-place had been found. Watch-houses overlooked it, but watchmen there were none. Drake had got touch with the maroons. By his directions a party of them had stolen down from the hills, and as the sentries came out from the city in the evening, swiftly and silently they had been every one dispatched. 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. As the Spaniards saw the fleet preparing the advance of the boats and pinnaces, the whole of the horse and a large force of foot marched out of the town to oppose the threatened attack, and took up a position fronting the sea, with their left resting on the town and the other flank exposed in the line of Carleill’s advance. It was exactly what had been foreseen, and, ere the Spaniards had discovered that the movement from the fleet was merely a feint, the horse which were covering their exposed flank were flying before Carleill’s musketeers.

The surprise was complete. 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. For an hour, alarms of drum and trumpet mingling confusedly with the sounds of street-fighting reached the listening fleet as the two columns forced their way to meet upon the Plaza. But how they fared none could tell, till on a tower a white staff suddenly appeared, and in another moment the cross of St. George fluttered gayly out upon the breeze. With a roar of triumph the ships’ guns saluted the signal of victory. The town was won.

Though the garrison fled panic-stricken across the river on the far side of the city, and the citadel was evacuated in the night, the place was far too large to be occupied by the force at Drake’s command. Following, therefore, the same tactics that had been successful at Nombre de Dios, he ordered the troops to entrench themselves in the Plaza and to occupy the principal batteries. In this way he held the city for a month.

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