With a desire for vengeance and embarrassed by the defeat suffered by Sir Francis Drake in 1795, the English Crown sent out a new expedition under the command of Sir George Clifford, Duke of Cumberland, assisted by Sir John Berkeley. The primary aim was to capture Brazil, which was then part of the Spanish Empire. However, according to some historians, England’s true intent was always to take Puerto Rico, known as the "Key to the Indies", and to add it to its empire.

After the attack by Drake, San Juan was left with a garrison of 200 men, together with some 150 volunteers. The five ships returned from Spain, bringing 200 soldiers for the new Governor, Antonio de Mosquera. Dysentery had laid many men low and there was so little food that the island was on the point of famine. Cassava bread and plantains were the only food they had. As a result of this combination of hunger and poverty, many soldiers had lost their military discipline and had become thieves.

On June 16, 1598, the English fleet appeared unexpectedly off the coast of the island. Clifford disembarked in El Condado and tried to get to San Juan, but the Spanish had burnt the water bridge and retreated to the bastion of Boquerón. Clifford almost drowned trying to cross the San Antonio channel, but was rescued by his men. They retreated with mounting casualties.

They attacked again on June 18 but by this time, the Spanish had retreated and taken refuge in the Castle of El Morro. During the next ten days the English fired only a few shots at the Castle, but they were well aware that the Spanish were suffering an epidemic of dysentery and were also short of food and munitions. Although they wanted to take the Castle, they had no intention of destroying it. On June 29, Clifford allowed the Spanish commander and his troops to leave El Morro and offered to transport them to Cartagena, but in actual fact he took them to Jamaica instead. The English sacked the city of San Juan but the dysentery epidemic attacked them also, killing hundreds, and for this reason, Clifford departed.

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San Juan National Historic Site, Fort San Cristobal, Norzagaray Street, San Juan, PR 00901
Telephone: (787) 729-6777
Last Update: March, 2000