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Florida and the Pirates

Pirate Chaos

In the confused dark, the pirates seemed everywhere. They destroyed the weapons in the guardhouse and went on to the government house. Shouting, cursing, they scattered through the narrow streets and seized or shot frightened, half-naked, bewildered people who erupted out of the houses. Painting by Robert Hall.

On May 28, 1668, a ship hove to and anchored off St. Augustine harbor. It was a vessel from Veracruz, bringing flour from Nueva España (México) to feed the soldiers and their families in Spanish Florida.

In the town, the drum called the garrison-120 men-to the alert. A launch went out to recognize the newcomer and put the harbor pilot aboard. As they neared the ship, the crew on the launch hailed the Spaniards lining her gunwale. To the routine questions came the usual answers: Friends from Nueva España-come aboard! Two shots from the launch told the town of the recognition, then the seamen warped her alongside the ship.

In St. Augustine, the people heard the signal shots, and rejoiced. The soldiers racked their arms in the main guardhouse on the town plaza. Tomorrow the supplies would come ashore.

As the launch pilot stepped aboard the supply ship, an alien crew swarmed out of hiding and leveled their guns at him and the others. He could do nothing but surrender.

About one o'clock that night, a corporal was out on the bay fishing when he sensed the ominous warning that shattered the serenity of the spring night: many oars were pulling across the water toward town. Desperately the fisherman paddled his little craft toward shore. The pirates, four boatloads of them, chased him hotly. They shot him twice, but he got to the fort anyway. His shouts aroused the guards.

Incorrect St. Augustine Drawing

St. Augustine never really looked like this! The sketch, from an "armchair travel" book of 1670, is the artist's fanciful interpretation of a written description. Mistranslation of the Spanish word "montes" (which can mean either forests or mountains) probably accounts for the background mountains. The faintly oriental aspect may be a carryover of the early concept that the New World was part of the exotic Orient.

At the main guardhouse, a quarter mile from the fort, the sentries heard the shouting and the gunfire. Then the pirates were upon them, a hundred strong. The handful of guards, being both out-numbered and practical, ran for the fort. Governor Francisco de la Guerra rushed out of his house and, with the pirates pounding at his heels, joined the guard in the race for the fort. Behind its rotten wooden walls with 33 men, somehow he beat off several assaults. But in the darkness the firefly glow of the matchcord that each arquebusier carried was an inviting target for the enemy.

In the confused dark, the pirates seemed everywhere. They destroyed the weapons in the guardhouse and went on to the government house. Shouting, cursing, they scattered through the narrow streets and seized or shot frightened, half-naked, bewildered people who erupted out of the houses.

Sergeant Major Nicolás Ponce de León, the officer responsible for defending the town, was at home, a sick man, greasy with unction of mercury and weak from the "sweatings" prescribed for him. On hearing the din, he roused himself and rushed to the guardhouse, only to find the pirates had been there first. He turned to the urgent task of shepherding his 70 unarmed soldiers and the others, men, women, and children, to the woods. This he did, leaving the pirates in complete possession of the town.

By daybreak the little force at the fort had lost five men, but they claimed 11 pirates killed and 19 wounded. Ponce came from the woods and reinforced the fort with his weaponless men. Also with the daylight, two vessels joined the Veracruz ship. One was St. Augustine's own frigate, taken by the raiders near Habana. In her, the pirates had been able to move in Spanish waters without detection. The other was the pirates' own craft. All three sailed into the bay, passed the cannon fire of the fort, and anchored just out of range.

Early Fort Plan
Early sketch of the fort in St. Augustine. Possibly from 1593 according to A Descriptive List of Maps by Lowery.

Although their attacks on the fort had failed, the pirates systematically sacked the town. No structure was neglected, from humble thatched dwelling to royal storehouse, hospital, and church. True, the things carried off were but worth a few thousands pesos (pieces-of-eight), for the town was very poor. The booty went aboard the pirate vessel and the ship from Veracruz.

That afternoon, the governor sent out a sortie from the fort, but the leaders were wounded and the party retired. After 20 hours ashore, however, the pirates were ready to leave anyway, and their last boat soon pulled away. Behind them, they left a grief-wracked people 60 of the little community were dead.

But with the tears came prayers of thanksgiving, for the pirates did not hoist anchor until they had ransomed their prisoners-about 70 men, women, and children for water, meat and firewood. At the last minute they refused to let the Indians go, claiming that the governor of Jamaica told them to keep all Indians, blacks and mulattoes as slaves, even if they were Spanish freemen. Finally on June 5 the raiders headed out to sea, well enough amused as once again they passed the thunder of the useless guns in the old wooden fort.

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