On their way home they fell in with a Portuguese ship laden with sugar, hides, and silver. Full of joy at their good speed they resolved upon going home. Captain Lister was sent in the prize to Portsmouth. He was wrecked at Helcliff, in Cornwall; all in her was lost, and only five lives saved. The Earl was delayed so long by bad weather that drink began to fail, and they had to collect what they could in sheets during a storm of rain. Many licked the moist boards and masts with their tongues, like dogs. In every corner of the ship were heard the lamentable cries of the sick and hurt, ten or twelve men died every night. Yet, we are told, the Earl ever encouraged his men by his presence of mind and his example; then they spoke a vessel which helped them with a little beer, and at last they put into Ventre-haven on the west coast of Ireland.

On arriving in London, as if the Earl had not suffered enough already, news was brought him that his eldest son was dead. But shortly after came another messenger announcing the birth of a daughter; this was the Lady Anne Clifford, who became, first, Countess of Dorset, and then of Pembroke. In this voyage thirteen prizes had been taken, and the profit doubled the outlay on his adventure in spite of the loss of his richest prize. It is difficult to realise the exceeding bitter feeling that existed between Spain and England at that time—a bitterness sharpened by religious differences, and kept in memory by private revenge.

For instance, Hakluyt tells us of a small English ship of about forty tons which was captured on the seas. Her crew were put by the Spaniards under hatches and coupled in bolts together; these men, after they had been prisoners three or four days, were murdered by a Spanish ensign-bearer, who had had a brother killed in the Armada fight, and who wished to revenge his death. This man took a poniard in his hand and went down under the hatches, where he found eight Englishmen sitting in chains, and with the same poniard he stabbed six of them to the heart; the remaining two clasped each other about the middle and threw themselves into the sea and there were drowned.

It is only fair to say that this act was much disliked by the other Spaniards, who carried the ensign-bearer a prisoner to Lisbon. The King of Spain willed he should be sent to England, that the Queen might treat him as she thought good; however, his friends interceded that he might be beheaded instead. On a Good Friday, as the Cardinal was going to Mass, captains and commanders stopped his Eminence and entreated for the man's pardon, and in the end they got his pardon, and his life was saved.

In 1592 the Earl of Cumberland hired the Tiger of 600 tons, and with his own ship the Samson, the Golden Noble, and two small vessels, he set forth. Contrary winds kept him east of Plymouth so long that it became too late to intercept the outward-bound carracks, so the Earl transferred his command to Captain Norton and returned to London. After some hard fighting the ships returned with a richly laden carrack. The narrator of the voyage moralises upon the happy finding thus: "I cannot but enter into the acknowledgment of God's great favour towards our nation, who, by putting this purchase into our hands, hath manifestly discovered those secret trades and Indian riches which hitherto lay strangely hidden from us ... whereby it should seem that the will of God for our good is to have us communicate with them in those East Indian treasures, and by the erection of a lawful traffic to better our means to advance true religion and His holy service." The pious sailor then goes on to enumerate the goods that were stored in the holds of the Spanish carrack—from jewels and silks of China to spices and carpets of Turkey—in all estimated to be worth £150,000. This was of course to be divided amongst the adventurers.

But exaggerated expectations ended in general discontent, for the Queen had one small ship at the capture of the carrack, and because the Earl was not commanding in person his share was adjudged to depend on her Majesty's mercy and bounty. The royal lioness "dealt but indifferently with him." She took her share, and the other jackals helped themselves as largely as they dared; so that the Earl was fain to accept of £36,000 for him and his, as a pure gift. The carrack was unloaded at Dartmouth, and being so huge and unwieldy she was never removed from the river, "but there laid up her bones."

The spirit of adventure in the Earl was not quenched by this disappointment, for in the latter end of 1593 he got ready two ships royal and seven others, which set sail next spring. Off the isle of Flores he met the Portuguese fleet and had to stand off to avoid them, as they were too numerous to attack. He was taken ill and would have died, had not Monson gone ashore on Corvo and stolen a milch cow, which they brought aboard. Twelve hulks yielded him some treasure, and he left for home after a gainful voyage.

Three of his ships he had sent to the West Indies, and they made for the pearl fisheries at Margarita. A Spaniard treacherously showed them where the pearls were stored in a ranckeria; they surprised it by night with twenty-eight men and carried off £2000 worth of pearls. Coasting along, two of them fell in with seven ships, moored alongside head and stern, and fought all day, hammer-and-tongs. The Spaniards got into their boats next day and made for the land, carrying the rudders with them; the English helped themselves and fired the ships. They then brought the chief ship of 250 tons safely to Plymouth.

Next year the Earl set forth on his eighth voyage, and in June came in sight of a big Indian ship whose name was Las Cinque Llagas ("the Five Wounds"), and she carried 1400 persons, of whom 270 were slaves.

The Earl's Mayflower was the first to get up to her, and was hotly fired into; for the Portuguese had sworn to defend their ship to the last, and fought with desperation. Don Rodrigo de Cordoba, having both his legs shattered, cried out, "Sirs, I have got this in the discharge of my duty. Be of good heart. Let no one forsake his post; let us perish rather than be taken."