San Juan de Ulúa Battle of 1568: John Hawkins and Francis Drake

San Juan de Ulúa

On September 16, 1568, Hawkins and Drake sailed seven ships single file toward San Juan de Ulúa with the English flag flying. Only two ships would make it back out again. Hawkins commanded one and Drake the other. Forever after this battle, these two Englishman would hold a burning hatred for the Spanish that would shape history.

Unintentional Trip to San Juan de Ulúa

Hawkins and Drake ended up near San Juan de Ulúa by accident on their fourth Caribbean slave run. Before their more well-known exploits as privateers for Queen Elizabeth, Hawkins and Drake had tried their hands as slave traders in the Caribbean. Their progressively risky slave-trading voyages ended with a narrow escape from angry Spaniards and angrier weather in September 1568. This voyage led their seven ships deep into Spanish territory in the Bay of Campeche with a disabled ship and their remaining 40 slaves left suffering in the hold. Their only option was to attempt a landing at Veracruz for repairs.

As the ships neared Veracruz, they were mistaken for the Spanish fleet that was due to arrive any day. Francisco de Bustamante, the lieutenant treasurer of Veracruz, went out to welcome the fleet only to end up a hostage of the Englishmen. The mistake was repeated with the commander of the Spanish garrison at San Juan de Ulúa, Antonio Delgadillo. By the time Delgadillo realized his error, Hawkins and Drake’s ships were within cannon range of the fort.

Negotiation, Mediation, and Intimidation

Hawkins tried desperately to keep his visit to San Juan de Ulúa civil. He knew he was outnumbered and outgunned. He immediately sent out official correspondence indicating his dilemma, explaining that he was only there by “force of weather” and requesting safe harbor to repair the Jesus of Lubeck. Knowing that the Spanish fleet was due any day, he hoped that “…there might no cause of quarrel rise…”

On September 17, 1568, the Spanish fleet received news of Hawkins’ position in San Juan de Ulúa. Hawkins had proposed to Delgadillo that while the Jesus was being repaired hostages would be exchanged on both sides to keep everyone civil, not an uncommon practice in the Spanish Main in negotiations between opposing European nations. Don Martin Enriquez de Almansa, the newly appointed Viceroy of New Spain traveling with the Spanish fleet, immediately took command of the situation. Feigning acceptance of Hawkins’ terms, he instead dispatched a request for additional Spanish troops. A mistrustful game of cat and mouse ensued between Hawkins and Enriquez, each preparing for the confrontation that would inevitably ensue. For his part, Hawkins had transferred the majority of his men and goods from the smaller ships to the Jesus and Minion and positioned guns and men on the island fort with the Spaniards.

Battle of San Juan de Ulúa

Enriquez’ plan involved a small party of 150 men boarding the Jesus and Minion with another party dispatched to take the island guns Hawkins had mounted on land. However, Hawkins noted suspicious Spanish activity on the day of the attack, September 23, 1568. His suspicions were confirmed when one of the Spanish hostages on the Jesus rose up with a dagger to stab him during his 10 O’clock meal. The angered Hawkins retaliated by shooting an arrow at Spanish Admiral Juan de Ubilla, but this missed and allowed the latter to signal Enriquez to begin his attack.

Hawkins’ men on shore were the first to be overpowered. All but three were killed and the Spanish took control of the fort and its cannons almost immediately. The Englishmen’s only chance was to flee, but the ships were under fire and badly damaged. The Jesus, with “..five shot through her main mast…” was abandoned. The Judith, anchored farthest out and captained by Drake, abandoned Hawkins before being damaged. Knowing all would be lost, Hawkins managed to transfer most of the gold and silver to the Minion but little else. The slaves and their provisions were left behind on the Jesus. Hawkins narrowly escaped on the Minion with 200 men on board. Those left to battle for six more hours after his departure were either killed or became long-time residents of Spanish dungeons.

Hawkins’ voyage back to England was yet another exercise in survival for the Englishman. Without the proper provisions, he and his crew barely survived the trip, arriving in Cornwall on January 25, 1569. Despite saving the gold and silver, the trip was not profitable after taking into account the lost ships and cargo. This last slave run served more as a lesson learned for both Hawkins and Drake; and what they learned, despite heavy losses, was that the Spanish were vulnerable.


  1. Carini, Marco & Macallan, Flora. Pirates: A Swashbuckling Journey across the Seven Seas. New York.
  2. Kraus, Hans P. Sir Francis Drake: A Pictorial Biography.
  3. Lane, Kris. Pillaging the Empire: Piracy in the Americas. U.S. 1998.
  4. Latimer, Jon. Buccaneers of the Caribbean: How Piracy Forged an Empire. Massachusetts, 2009.
  5. Rogozinski, Jan. A Brief History of the Caribbean: From the Arawak and the Carib to the Present. New York. 1999.
  6. Wood, Peter. The Seafarers: The Spanish Main. Time-Life Books. VA. 1979