History Timeline 1500s

Above: Painting, entitled Discovery of the Mississippi, by William H. Powell, 1847, is located in the Rotunda of the Capitol in Washington, D.C. Right: Giovanni de Verrazzano, 1889, engraving by F. Allcarini, Tocchi, courtesy Wikipedia Commons.

Giovanni da Verrazzano

Pre-Revolution Timeline - The 1500s


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  • Timeline

  • Detail - 1598

    June 15, 1598 - Royal Navy of England attacks Puerto Rico with twenty-one ships under George Clifford, conquering the island and holding it for several months before abandoning it back to Spanish authority.

    Battle of San Juan 1598

    George Clifford, the Earl of Cumberland, was a famous privateer, taking ten missions to blast the Spanish at locations around the world, particulary in the West Indies. He had built the biggest ship ever, eight hundred tons, and under the tutelage of Sir Henry Lee, who promoted the exercise of arms, Clifford had taken to the sea.

    Problem was, the Spanish, under Philip II, had built the most formidable empire. They controlled the Italian, Portuguese, and the Netherlands, had the whole of East Indian trade, as well as ore from South American mines. But with so much wealth, the Spanish were getting lazy. They neglected their own agricultural health, and started to become targets of the English and other privateers searching for the weak Spanish ships carrying precious treasure.

    Lord Cumberland was planning his greatest mission ever in 1598, most funded by his own money. He had twenty ships under sail, (some say twenty-one) including the Old Frigate and two barges to land troops upon attack. He commanded the six hundred ton ship called the Scourge of Malice as its Admiral. Sir John Berkeley commanded the four hundred ton Merchant-Royal as Vice Admiral. On March 6, 1598, they sailed, with one thousand seven hundred men, from Plymouth, England.

    They quickly got intelligence that the Spanish were sending treasure back to the Indies on five caracks acompanied by twenty-five ships bound for Brazil. However, those ships got word that Admiral George Clifford was on the seas and stayed in port. The mission had to make due with a ship filled with corn, copper, and powder, plus a French ship carrying salt, and two Flemings with corn as they made their way to the South Cape.

    When they reached Lanzerota, the northeastern most island of the Canary Islands, he anchored the fleet on its southeast coast. A Spanish marquis had built a castle there, with two hundred guards. Sir John Berkeley took six hundred of his men to raid and took it without a fight; the guardsmen abandoning it.

    By May 23, 1598, the fleet had reached Dominica and the Virgin Islands. They rested there one month as the Earl of Cumberland made his next plan, to capture San Juan de Puerto Rico, the recent attempt at which Sir Francis Drake had failed. The men cheered.

    The Battle of San Juan

    It was June 6, 1598 when Clifford's fleet reached the island; his attempt to capture was different than Drake. The Earl of Cumberland landed one thousand men far from the town and marched toward it. The Earl and Berkeley were armored, but upon reaching near the town, had an arm of the sea separating them from their goal in a position that was exposed to fire from the fort, El Moro, built in 1539, and now known as the fortress Castillo San Felipe del Morro, opposite them.

    San Juan was a strong target, bigger than Portsmouth, with several large streets, a monestary and cathedral. Problem was access to it; only a small causeway, named San Antonio, was passable, and it was easily defended by the fort which was built above it. So instead, the English waded beside it, in darkness.

    Their first attack failed and the Earl became ill and almost drowned. His troops, which were fighting from the water, had to retreat. The next attack had more success, a party of musketeers picked off the Spanish cannoneers. Another party was sent ashore midway between the fort, garrisoned with two hundred and fifty men, and the town. The Spanish, with their retreat cut off, abandoned the fort after a siege of fifteen days, and fell back to the town, which Cumberland had ransacked.

    In quick succession, the three forts of San Juan, including El Moro, surrendered on the terms Clifford imposed on the Spanish governor Antonio Mosquera. The Earl of Cumberland now controlled San Juan. He told the Spanish residents to leave for other islands, within several weeks they were repatriated to Caragena, and asked for volunteers from his English crew to remain as the nucleus of an English colony. However, his plan would fail. Seven hundred of the men who landed became sick and died. Clifford tried to negotiate a ransom with the Spanish, but they stalled, waiting for the sickness to further weaken his force.

    With the negotiations pending, a caravel from Margarita, Venezuela came to the harbor, surprised that it was now in English hands, then lost the pearls on board worth one thousand ducats. The Earl heard that a large chest of pearls was back at Margarita, so he sent three ships to sieze it. Adverse winds prevented the capture, so Clifford took half his fleet to search for treasure elsewhere on August 14, 1598. Sir John Berkeley was left in charge of San Juan with the other half and was given the power to act.

    It is unknown how John Berkeley treated or what terms were made with the colonists, but a storm hit the harbor, severely damaging his fleet. Berkeley left in September to be reunited with Clifford at Flores, returning to England in October. The English conquest of Puerto Rico only lasted forty to sixty-five days, depending on the account, although the Earl of Cumberland came away with much treasure, eighty pieces of cannon, two thousand slaves, and more. It is questioned whether the expense of the enterprise was overcome by the treasure gathered. He did, however, gain a patent from the Queen.

    Image above: Drawing of the English assault in the 1598 Battle of San Juan, 1873, British Battles on Land and Sea. Courtesy Wikipedia Commons. Image below: 4th level of he El Morro fort, date unknown. Courtesy National Park Service. Source info: "British Battles on Land and Sea," 1873, James Grant; Wikipedia, National Park Service.

    El Morro Fort

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