7. In 1595, this famous (or perhaps infamous) Englishman and his fleet attacked the Spanish at the port of San Juan but failed to capture it. Who was this vice admiral, navigator, and privateer who was the bane of Spain?
From Quiz Important Dates in the History of Puerto Rico
Answer:
Sir Francis Drake
While often victorious against the Spanish elsewhere, Sir Francis Drake lost the Battle of San Juan, as it was to be called. In fact, he himself nearly died when a cannonball blasted through his cabin on board the flag ship. He did indeed die a few weeks later in January of 1596 due to dysentery, and he was buried at sea. Divers still search for his coffin to this day.
In 1598, George Clifford, the Third Earl of Cumberland, and his men did manage to capture San Juan for the English Crown. However, he was not able to hold it because of the loss of soldiers to disease.