|San Juan de Ulua saw Hawkins' 4th Expedition to the Caribbean come to an ignonomious end at San Juan de Ulua. Hawkins’ lookouts could see what looked to be ships, but were unable to tell how many. They didn’t show any English flags while entering port, and the suspected ship was actually just a Spanish hulk. They were cautiously gliding into San Juan when the Spanish on the beach opened fire. Dense clouds of smoke covered the water. Hawkins was about to return fire when he realized the Spanish weren’t firing in anger, but as a salute. The Spanish mistook his fleet for the Spanish treasure flota. Hawkins and his fleet sailed into port completed untouched.
By the time the Spanish had realized their mistake it was too late. The island was in panic. Everyone dropped what they were doing and began rowing. Some men even ran into water and began swimming. A single person remained: the garrison commander, Captain Antonio Delgadillo. Hawkins sent his second-in-command to speak with him. Though phrased as a question, Delgadillo was more or less told that Hawkins was going to be refitting and repairing his ships. Delgadillo had no choice but to agree, as the fleet was already in port, and he was outnumbered and outgunned. Hawkins’ ship alone, The Jesus of Lubek, had 47 guns. As insurance, Hawkins took two hostages aboard: a nobleman named Villaneuva, and a local official named Francisco de Bustamente.
The next morning, Hawkins’ lookouts called him up on deck. There were sails on the horizon. Hawkins called Bustamente up as well to confirm his suspicion that the Spanish flota had arrived. Hawkins allowed the Spanish to enter port, but only on his terms. He sent Delgadillo to the Spanish flota in a small boat to tell them these terms. To no surprise, the Spanish flagship’s captain, Viceroy Don Martin Enriquez, was less than impressed and resented the idea of negotiating with pirates, especially those who violated Spanish territory. However, the Spanish were also running low on food and supplies, so they had no choice but to enter San Juan on Hawkins’ terms.
The arguing over terms took all night and most of the morning, likely because Delgadillo was making a nine mile trip in a small boat each time either side had something to say. Finally, they had agreed, and the agreement was signed by both parties, though bad weather delayed the Spanish from entering for two days. Once they did enter, the port was so tightly packed with ships that people could walk across the decks from ship to ship.
That night, a man from Hawkins’ crew went to wake Hawkins, to inform him that he and others had been hearing noises. Hawkins was awake prior to this, and had been hearing them as well. The Spanish were moving what sounded like armed men into the hulk, which served as a bridge between the Spanish and English ships, they were filling it with soldiers so that they could storm across deck to Hawkins’ ships without warning. Hawkins confronted the Spanish Viceroy in the morning, but he denied any plan of attack that the Spanish may have. That night at dinner, Villanueva attempted to kill Hawkins with a dagger. Hawkins had him bound and thrown in his room.
Hawkins grabbed a crossbow then proceeded to the deck. Less than 20 yards away, he saw armed Spanish soldiers on the deck of the hulk. “Is this Spanish treachery?” he called out.All at once, the Spanish soldiers stormed out of their ships and swarmed across the beach. The English parties that were guarding the gun batteries were overtaken, and killed instantly. Spaniards were running and jumping from the hulk onto one of Hawkins’ ships, the Minion, flailing their swords. Chaos ensued.
Hawkins and his fleet were getting massacred. To escape the battle, they had to warp-out. This was a slow and tedious method under normal conditions. Hawkins and his remaining ships eventually made it out of the range of the Spanish, but the Spanish had one more ploy. Using a ship that was heavily damaged by Hawkins’ fleet, the Spanish implemented a kamikaze type tactic, lighting the ship on fire and sending it in the direction of John Hawkins. Luckily the ship turned off course and missed the remaining ships in Hawkins’ fleet.
Hawkins finally escaped San Juan de Ulúa. He lost four ships, and 500 men. The Spanish had captured three of these ships, and sunk a forth, only losing one ship and 20 men of their own in the process. Only two ships in Hawkins’ fleet remained, The Minion, and The Judith. Hawkins commanded one, and Drake the other. After this battle, the two Englishman would hold a burning hatred for the Spanish that they nurtured with devastating skill over the coming years. Despite being a defeat, this battle marked a turning point for English fortunes in the Caribbean. From this point onwards, they took the battle to the Spanish and challenged them for supremacy of the seas initially and the islands latterly.