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 - 1595

    November 22, 1595 - Sir Francis Drake, an English privateer, lands in San Juan Bay, Puerto Rico, to loot the city with twenty-seven ships and two thousand and five hundred soldiers. Spanish forts defeat the raid.

    Fort El Morro

    Since the destruction of St. Augustine in 1586 by Sir Francis Drake and his English counterparts, it was becoming more and more clear that Drake, while still doing the bidding of the English crown, was becoming less an explorer or admiral, and more of a privateer. Yes, he had done good deeds for the English crown, rescuing the first settlers at Roanoke colony on his way back in 1586; defeating the Spanish Armada in 1588 as it attempted to attack England.

    However, he was beginning to lose the luster once bestowed upon him. The Drake-Norris expedition against the remaining ships of the Spanish Armada ended with destruction of the town of Vigo, but also the loss, on the entire journey, of over twelve thousand men. An investigation ensued; Drake was reduced to coastal commander of Plymouth and was given no naval command for six years.

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    Drake's Return To Service Again

    By 1595, he was back in command on the seas, but still finding trouble having the success of his earlier exploits. He was defeated at Las Palmas in the Canary Islands, then followed that up with various defeats in Spanish America. Finally, Drake, back in England, was given another assignment by Queen Elizabeth I despite the former defeats. Attack the capitol of San Juan, Puerto Rico, loot the town for its gold and silver, and in the offing, Drake could get back his reputation with the crown. That did not happen.

    The Spanish had been much more careful about building their defenses in San Juan than they had been in the newer colonization efforts at St. Augustine. Fort San Felipe del Morro had been constructed in 1539 through 1591. It was part of a plan to build nine forts of significant size ( Santo Domingo, Santa Marta, Cartagena, Nombre de Dios, Portobelo, the Chagres River, Panama City, Havana, and St. Augustine) to prevent the previous English successes. El Morro was built to protect the harbor of San Juan and thwart an attack by sea.

    Ordered by Queen Elizabeth I of England to attack Puerto Rico and Panama, Drake left Plymouth, England on August 25, 1595, accompanied by fellow commander Sir John Hawkins, twenty-seven ships and twenty-five hundred men. There were reports that a ship carrying two million pounds of pesos had been battered by a storm on its way from the islands to Spain and was now in port at San Juan for repairs. However, Spain was not going to wait for the repairs to happen, they sent five frigates under Admiral Pedro Tello de Guzmán to retrieve the treasure. On the way, he captured one of Drake's ships, the Francis, and learned of the English plan. He hastened forward ahead of Drake.

    Shore defenses were ready, the fort was positioned with seventy cannons, and Tello sank two vessels in the harbor and positioned his five frigates behind them. There were seven hundred Spanish soldiers waiting onshore and eight hundred on the frigates.

    Drake arrived in Puerto Rico on November 22; Hawkins had died a few days before. They anchored in Boquerón Inlet; the Spanish bombarded them there. They moved the next day to the Isla de Cabras and formulated a plan. First, they would attack the frigates at night.

    "Captain Poore and mysealfe had the comande of this service; for the regiments. Captain Salisburie comandinge; the grand captain companye was sent by the generalls; diverse sea commanders were also sent; and on the thirteenth at night passinge in harde under the forte, we set three of them on fire; only one of which, it was my chance to undertake, was burnt; on the others, the fire held not by reason that being once out they were not maintained with newe. The burnte shippe gave a greate light, the enemie thereby playinge upon us with their ordi- nance and small shotte as if it had been fayre daye, and sinkinge some of our boates : a man could hardly comande his mariners to row, they foolishly thinkinge every place more dangerous than where they were, when, indeede, none was sure. Thus doinge no harme, we returned with two or three prisoners, when, indeede, in my poore oppinion, it had binne an easier matter to bringe them out of the harborowe than fire them as wee did, for our men aboard the shippes numbred five thousand one hundred and sixty peeces of artillerie that played on us during this service; and it had binne less dangerous to have abidden them close in the frigotts and in the darke than as wee did; but great comanders many tymes fayle in theyre judgment, beinge crost by a compartner; but I had cause of more griefe than the Indies could pelde mee of joy e, losinge my Alfierez, Davis Pursell; Mr. Vaughan, a brother-in-law of Sir John Hawkins, with three others; Thomas Powton, with five or six more hurte and maimed; and was somwhat discomfited, for the generall feigned heere to set up his rest ; but examininge the prison- ers, by whom hee understoode that these frigotts were sent for his treasure, and that they would have fallen amonge us at Guadalupe had they not taken the Francis, his minde altered: callinge to counsaile, he comanded us to give our opinions what we thought of the strength of the place. Most thought it would hazard the whole action. But one Rush, a captaine, more to mee aleadged that without better puttinge for it, [than by] the bare lookinge upon the outside of the forts, we could hardly give such judgment; and I set it playnely under my hande, that if we resolutely attempted it, all was ours; and that I persuaded mysealfe no towne in the Indies could yielde us more honnor or profitte. The generall pre- sently saide: "I will bring thee to twenty places farre more wealthye and easier to be gotten." Such-like speeches I thinke had bewitched the coronell, for he most desired him to hasten him hence," Sir Francis Drake his Voyage, 1595," Maynarde, Thomas, fl. 1595; Cooley, William Desborough, 1883.

    By November 25, 1595, Drake gave up the effort to take San Juan and its treasures and left for South America. They looted the towns of Rio de la Hacha, La Rancheri´a, Tapia, and Santa Marta, then headed for Panama. He and fellow commander Thomas Baskerville decided to attack the Spanish Main by the Nombre de Dios so that a crossing of the isthmus was possible. However, it was foolish. His goal to capture the whole of Panama failed miserably. By January 27, there were only thirty-seven fit men not ravaged by disease; one was Drake, who died a few days later.

    Image above: For El Morro protecting San Juan Bay, 2006, Mtmdfan. Courtesy Wikipedia Commons. Below: Montage (background) photo of the replica of the Golden Hind in London, 2007, Josef L. Marin. Courtesy Wikipedia Commons CC3.0; (inset) portrait of Francis Drake, circa 1590, Marcus Gheeraerts the Younger. Courtesy Buckland Abbey via Wikipedia Commons. Source info: Library of Congress; "Sir Francis Drake his Voyage, 1595, Maynarde, Thomas, fl. 1595; Cooley, William Desborough, 1883; Wikipedia.

    Sir Francis Drake and the Golden Hind

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