Was it policy, or love of adventure, or just desire for gain? The Earl soon began to form schemes for sending ships to plunder the Spaniards; he fitted out at his own cost the Red Dragon of 260 tons, and the barque Clifford of 130. Raleigh sent a pinnace to join them, and they sailed in 1586 under the command of Robert Withrington. They took a few merchantmen on their way to Sierra Leone; the principle on which they acted was a mixture of courtesy and bullying. Hakluyt says: "Our Admiral hailed their Admiral with courteous words, willing him to strike his sails and come aboard, but he refused; whereupon our Admiral lent him a piece of ordnance" (it sounds so kind and friendly) "which they repaid double, so that we grew to some little quarrel." The result was that the English boarded the hulks and helped themselves. For they found the hulks were laden in Lisbon with Spanish goods, and so thought them fair game. When they reached Guinea they went ashore, and in their search for water and wood came suddenly upon a town of negroes, who struck up the drum, raised a yell, and shot off arrows as thick as hail.
The English returned the fire, having about thirty calivers, and retired to their boats, "having reasonable store of fish"; "and amongst the rest we hauled up a great foul monster, whose head and back were so hard that no sword could enter it; but being thrust in under the belly in divers places, much wounded, he bent a sword in his mouth as a man would do a girdle of leather about his hand: he was in length about nine feet, and had nothing in his belly but a certain quantity of small stones." Later on they found another town of about two hundred houses and "walled about with mighty great trees and stakes, so thick that a rat could hardly get in or out." They got in, for the negroes had fled, and found the town finely and cleanly kept, "that it was an admiration to us all, for that neither in the houses nor streets was so much dust to be found as would fill an egg-shell." The English found little to take except some mats and earthen pots; was it for this that they, on their departure, set the town on fire? "It was burnt in a quarter of an hour, the houses being covered with reeds and straw."
Thence they sailed across to America, having no little trouble with a disease which they had caught ashore. They came to Buenos Ayres, where was great store of corn, cattle, and wine; but no gold or silver was to be had. Here they fell into some contention as to their further course, but as food was growing scarce they sailed northwards, till they came to Bahia, where they met a hot welcome of balls and bullets, but took some prizes. Then came a storm, and some of their prizes got loose and were lost. "Anon the people of the country came down amaine upon us and beset us round, and shot at us with their bows and arrows."
Of another fight which occurred shortly after, when the barque Clifford was boarded by the enemy, the merchant Sarracoll says: "Giving a mighty shout they came all aboard together, crying, 'Entrad! Entrad!' but our men received them so hotly, with small shot and pikes, that they killed them like dogs. And thus they continued aboard almost a quarter of an hour, thinking to have devoured our men, pinnace and all ... but God, who is the giver of all victories, so blessed our small company that the enemy having received a mighty foil was glad to rid himself from their hands: whereas at their entrance we esteemed them to be no less than betwixt two and three hundred men in the galley, we could scarce perceive twenty men at their departure stand on their legs; but the greater part of them was slain, their oars broken and the galley hanging upon one side, as a sow that hath lost her left ear, with the number of dead and dying that lay one upon another." While this terrible havoc was a doing, others of the crew had gone ashore and fetched sixteen young bullocks, "which was to our great comforts and refreshing."
After committing what havoc they could along the coast, with little profit to themselves, the commander resolved to go home; which resolution was "taken heavily of all the company—for very grief to see my Lord's hopes thus deceived, and his great expenses cast away."
The Earl took part in the Armada fight on board the Bonadventure, and the Queen, to mark her approbation, gave him a commission to go the same year as General to the Court of Spain, lending him the Golden Lion; this ship he victualled and furnished at his own expense. After taking one merchant ship and weathering a storm, he was obliged to turn.
But the Queen was his good friend and lent him the Victory, and with three smaller ships and 400 men he sailed from Plymouth in 1589. We do not hear what his Countess thought of so much wandering into danger, but duty, or profit, called her lord to the high seas. He made a few prizes, French and German, for he was not too scrupulous about nationalities, and made for the Azores, where he cut out four ships. At Flores he manned his boats and obtained food and water from Don Antonio, a pretender to the throne of Portugal. As they were rowing back to their ship, "the boat was pursued two miles by a monstrous fish, whose fins many times appeared above water four or five yards asunder, and his jaws gaping a yard and a half wide, not without great danger of overturning the pinnace and devouring some of the company"; they rowed at last away from the monster. They were now joined by a ship of Raleigh's and two others.
Meanwhile the richly laden vessels of Spain were on their way home, with orders to rendezvous at St. Helena. Some of the Earl's cruisers sighted them, but did not dare attack the huge carracks, though Linschoten tells us—and he was aboard one of them—that if the English had attacked they must easily have been taken; for scurvy, caused by bad food, was making ravages on the crews. "Every day men who had been some days dead were discovered in the places whither they had crept that they might lie down and die in peace." But all the English cruisers did was to insult them with reproaches and annoy them with musketry, and such small cannon-shot as vessels of thirty tons could carry. As Admiral Colomb used to say, "A captain of a man-of-war in those days could carry a cannon-ball in his coat-tail pocket," so small and light were they.
When the Earl was told that the West Indian fleet had sailed past, he returned to Fayal and took possession of the town, consisting then of some five hundred well-built houses; the inhabitants had abandoned it at his approach. He set a guard to preserve the churches and monasteries and stayed there four days, till a ransom of 2000 ducats, mostly in church-plate, was brought to him, with sixty butts of wine.
While taking two Brazilian ships at St. Mary's laden with sugar, the bar detained his vessel in a position exposed to the enemy; eighty of his men were killed, the Earl was wounded slightly in the side; "his head also was broken with stones, so that the blood covered his face, and both his face and legs were burnt with fire-balls."