This section is from the book "Elizabethan Sea Dogs", by Gerhard R. Lomer and Charles W. Jefferys. Also available from Amazon: Elizabethan Sea Dogs.
But again there was a dearth of booty. The Spaniards were getting shy of keeping too many valuables where they could be taken. So negotiations, emphasized by piecemeal destruction, went on till sickness and the lateness of the season put the English in a sorry fix. The sack of the city had yielded much less than that of San Domingo; and the men, who were all volunteers, to be paid out of plunder, began to grumble at their ill-success. Many had been wounded, several killed — big, faithful Tom Moone among them. A hundred died. More were ill. Two councils of war were held, one naval, the other military. The military officers agreed to give up all their own shares to the men. But the naval officers, who were poorer and who were also responsible for the expenses of their vessels, could not concur. Finally 110,000 ducats (equivalent in purchasing power to nearly three millions of dollars) were accepted.
It was now impossible to complete the programme or even to take Havana, in view of the renewed sickness, the losses, and the advance of the season. A further disappointment was experienced when Drake just missed the treasure fleet by only half a day, though through no fault of his own. Then, with constantly diminishing numbers of effective men, the course was shaped for the Spanish 'plantation' of St. Augustine in Florida. This place was utterly destroyed and some guns and money were taken from it. Then the fleet stood north again till, on the 9th of June, it found Raleigh's colony of Roanoke.
Ralph Lane, the governor, was in his fort on the island ready to brave it out. Drake offered a free passage home to all the colonists. But Lane preferred staying and going on with his surveys and ' plantation.' Drake then filled up a store ship to leave behind with Lane. But a terrific three-day storm wrecked the store ship and damped the colonists' enthusiasm so much that they persuaded Lane to change his mind. The colonists embarked and the fleet then bore away for home. Though balked of much it had expected in the way of booty, reduced in strength by losses, and therefore unable to garrison any strategic point which would threaten the life of New Spain, its purely naval work was a true and glorious success. When he arrived at Plymouth, Drake wrote immediately to Burleigh: 'My very good Lord, there is now a very great gap opened, very little to the liking of the King of Spain.'
This 'very great gap' on the American side of the Atlantic was soon to be matched by the still greater gap Drake was to make on the European side by destroying the Spanish Armada and thus securing that mightiest of ocean highways through which the hosts of emigration afterwards poured into a land endowed with the goodly heritage of English liberty and the English tongue.
The year of Drake's return (1586) was no less troublous than its immediate predecessors. The discovery of the Babington Plot to assassinate Elizabeth and to place Mary on the throne, supported by Scotland, France, and Spain, proved Mary's complicity, produced an actual threat of war from France, and made the Pope and Philip gnash their teeth with rage. The Roman Catholic allied powers had no sufficient navy, and Philip's credit was at its lowest ebb after Drake's devastating raid. The English were exultant, east and west; for the True Report of a Worthie Fight performed in the voiagefrom Turkie by Five Shippes of London against 11 gallies and two frigats of the King of Spain at Pantalarea, within the Straits [of Gibraltar] Anno 1586 was going the rounds and running a close second to Drake's West India achievement. The ignorant and thoughtless, both then and since, mistook this fight, and another like it in 1590, to mean that English merchantmen could beat off Spanish men-of-war. Nothing of the kind: the English Levanters were heavily armed and admirably manned by well-trained fighting crews; and what these actions really proved, if proof was necessary, was that galleys were no match for broadsides from the proper kind of sailing ships.
Turkey came into the problems of 1586 in more than name, for there was a vast diplomatic scheme on foot to unite the Turks with such Portuguese as would support Antonio, the pretender to the throne of Portugal, and the rebellious Dutch against Spain, Catholic France, and Mary Stuart's Scotland. Leicester was in the Netherlands with an English army, fighting indecisively, losing Sir Philip Sidney and angering Elizabeth by accepting the governor-generalship without her leave and against her diplomacy, which, now as ever, was opposed to any definite avowal that could possibly be helped.
Meanwhile the Great Armada was working up its strength, and Drake was commissioned to weaken it as much as possible. But, on the 8th of February, 1587, before he could sail, Mary was at last beheaded, and Elizabeth was once more entering on a tricky course of tortuous diplomacy too long by half to follow here. As the great crisis approached, it had become clearer and clearer that it was a case of kill or be killed between Elizabeth and Mary, and that England could not afford to leave Marian enemies in the rear when there might be a vast Catholic alliance in the front. But, as a sovereign, Elizabeth disliked the execution of any crowned head; as a wily woman she wanted to make the most of both sides; and as a diplomatist she would not have open war and direct operations going down to the root of the evil if devious ways would do.
So the peace party of the Council prevailed again, and Drake's orders were changed. He had been going as a lion. The peace party now tried to send him as a fox. But he stretched his instructions to their utmost limits and even defied the custom of the service by holding no council of war when deciding to swoop on Cadiz.
As they entered the harbor, the English saw sixty ships engaged in preparations for the Great Armada. Many had no sails—to keep the crews from deserting. Others were waiting for their guns to come from Italy. Ten galleys rowed out to protect them. The weather and surroundings were perfect for these galleys. But as they came end-on in line-abreast Drake crossed their T in line-ahead with the shattering broadsides of four Queen's ships which soon sent them flying. Each galley was the upright of the T, each English sailing ship the corresponding cross-piece. Then Drake attacked the shipping and wrecked it right and left. Next morning he led the pinnaces and boats into the inner harbor, where they cut out the big galleon belonging to Santa Cruz himself, the Spanish commander-in-chief. Then the galleys got their chance again—an absolutely perfect chance, because Drake's fleet was becalmed at the very worst possible place for sailing ships and the very best possible place for the well-oared galleys. But even under these extraordinary circumstances the ships smashed the galleys up with broadside fire and sent them back to cover. Then the Spaniards towed some fire-ships out. But the English rowed for them, threw grappling irons into them, and gave them a turn that took them clear. Then, for the last time, the galleys came on, as bravely but as uselessly as ever. When Drake sailed away he left the shipping of Cadiz completely out of action for months to come, though fifteen sail escaped destruction in the inner harbor. His own losses were quite insignificant.
 
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