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The Battle That Made Francis Drake Spain’s Worst Nightmare

Depending on one’s historical sympathies, Sir Francis Drake is one of the many characters who was either great or infamous. To the English, he was a daring, successful patriot. To the Spanish, everything to hate about lawless, Protestant aggression and the rising sea power to the north.

Francis Drake in 1591

Queen Elizabeth I knighted him after he circumnavigated the globe—the first Englishman to do so. The Spanish, meanwhile, dubbed him El Draque, or The Dragon, for the brazen piracy he carried out on that trip and countless others. 

Drake contributed more than anyone to causing the war in which England famously defeated the Armada in 1588. But mere patriotism and fear of Catholicism didn’t drive him to harass the Spanish. For Drake, it was personal. One battle drove him mad with vengeance and convinced him he could no longer trust or trade with the Spanish. 

The Battle of San Juan de Ulua

In 1568, Drake was a 28-year-old captain in a seven-vessel fleet led by his cousin John Hawkins. This was his second slave trading voyage to the Spanish colonies. The crew had recently unloaded its cargo in Cartagena, and the ships were weighed down with gold, silver, and all types of jewels. 

During Hawkins’s most recent voyage, he and his crew had been feted as heroes by court and countrymen alike. He had also made a 60 percent profit and become highly wealthy overnight. The haul he carried now promised to dwarf his previous journeys. 

On the way back to England, however, a violent storm hit the fleet off the coast of Cuba and drove it into the coast of Florida, badly damaging Hawkins’s ship, the Jesus of Lubeck. Running low on supplies and unsure if the Jesus of Lubeck would make it back to England, Hawkins decided to risk landing at the nearest port, San Juan de Ulua, off Veracruz.

This created considerable concern because the English were trading with Spanish colonists on the black market. Spain’s King Phillip II interpreted the Treaty of Tordesillas—which divided the world between the Spanish and Portugueseto mean that no other nation should colonize or trade in the Americas. 

Three years earlier, the Spanish had massacred a French Huguenot colony near present-day Jacksonville, Florida for being Protestant and being there.

On the way to San Juan, Hawkins’s fleet caught up with three Spanish vessels in the Gulf of Mexico. He planned to use the captured Spanish as leverage when he arrived at the fort.

When he landed at San Juan, the Spanish boarded the English ships, thinking they were boarding a Spanish fleet to pick up the gold and silver load in the port.

San Juan de Ulua Plaza

Hawkins assured them that his crew only wanted to resupply and repair its ships and would soon be on its way. To avoid conflict, though, he made the Spanish leave the island where the fort was. 

The following day, the expected Spanish fleet arrived, escorting the new viceroy of New Spain, Don Martin Enriquez de Almanza. 

Hawkins sent out a negotiating party. The Spanish agreed to anchor away from the English to avoid hostilities, and Hawkins and his company would repair their ships and pay for supplies. The Spanish, moreover, would not come armed onto the island. To ensure each side kept its word, they exchanged prisoners.

The Spanish captain, however, had instructions from Spain’s King Phillip to capture any foreign vessels found in the New World, and this presented an opportunity to impress his sovereign.

The Spanish amassed a force to take the batteries that Hawkins had taken over to protect his ships. They also snuck a couple of hundred men onto a vessel and sailed it between them and the English.

On the morning of September 23, the English became suspicious. When Hawkins confronted them through one of his captains who spoke Spanish,
Enrique ordered the English captain seized and gave the order to attack.
 
The concealed Spanish force rowed to the island and overpowered the English manning the batteries. They then turned the batteries on the English ships. Like with the French in Florida, the Spanish gave no quarter to prisoners.
 
Jesus de Lübeck took irreparable damage. Hawkins and as many men as could escape boarded the Minion, whose crew had managed to fight off boarding Spaniards and make it out of port.
 
Drake’s Judith and the Minion fled the port when the Spanish sailed two fire ships toward them. The Sp
1887 Depiction of San Juan de Ulua Battle
anish destroyed the other five English vessels.
 
The escaped ships were dangerously overcrowded, and Hawkins had to leave many of his men on the mainland, north of Florida, before returning to England. Only 70 or 80 ever made it alive back to England. Those whom Hawkins and Drake left behind to surrender to the Spanish were made galley slaves, beheaded, or burned at the stake for their Protestant heresy.

Aftermath

The Spanish lost two ships and multiple men in the battle. But their failure to annihilate the English crew created greater problems in the future.

This episode undermined attempts by the Spanish ambassador in London to ease tensions with England. It etched into the English consciousness that the Spanish could never be trusted to keep their word.

Although nearly two decades passed before open war broke out between the nations, Queen Elizabeth turned her approval from illicit trade with the Spanish colonists to outright piracy. Drake became one of the most notorious in this craft.

Drake already hated Catholics. As a child, his family had to flee a Catholic uprising in his native Cornwall. His family was forced to move and live in relative poverty because of this, and it led to his becoming a sailor rather than receiving a college education. The attack off the coast of Veracruz sealed his hatred of both Spanish and Catholics and led him to a life of vengeance against both.

After San Juan de Ulua, slave trading no longer interested him. To despoil the Spanish at sea or on land in the New World became his life’s mission.

Francis Drake’s Circumnavigation

In the 1570s, he allied with runaway slaves, known as cimarrones, to raid Spanish silver caches on the Spanish Main—today’s Venezuela and Colombia

Drake even compared his vengeance with divine retribution, saying:

As there is a general vengeance which secretly pursueth the doers of wrong and suffereth them not to prosper … so is there a particular indignation, engraffed in the bosome of all that are wronged, which ceaseth not seeking by all means possible to redress or remedie the wrong receive

King Phillip placed a reward of 20,000 ducats on his head, which today is $10 million dollars. 

Like the attack on the Huguenots in Florida, the Spanish justified their betrayal of their word to the English because the English were heretics. Furthermore, these traders were violating Spanish law and encroaching on what they considered Spanish seas.

England, meanwhile, benefited immensely from the Spanish treachery off Veracruz and Drake’s vendetta. His raids enriched England and bled the riches of the Spanish empire just as it reached its pinnacle of power and wealth.

Statue of Francis Drake next to Naval War Memorial in Devon, UK

Drake’s attacks on cities in Latin America during the 1580s prompted Philip to order the invasion of England. Drake, however, preemptively took the Spanish port city of Cadiz, where he captured six ships and destroyed 31 others. This delayed Spain’s invasion by three years. The defeat of the Armada when Spain finally attacked marked the beginning of the end of Spain’s superpower status.

Throughout history, what made individuals one nation’s patriots made them other nations’ menaces. Spain’s jealous mercantilism and Catholic fanaticism turned Drake from an illegal trader into a lifelong enemy and pirate. After the battle of San Juan de Ulua, he did everything he could to drive Spain to war with his nation—a dangerous gamble for England—but one that paid off, thereby switching the balance of power in world history.   

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