Pirates, Spies, and Submarines (Part 2 of 2)


When you visit St. Augustine, Florida, the most prominent building, is the fort Castile De San Marcos. The flags of several nations have flown over the fort, but it has never been taken in battle. This is the fort’s great claim to fame. The Castillo was built between 1672 and 1675 using local materials. But, what most people do not know is that the fort was not built to protect St. Augustine from foreign nations, it was built to protect St. Augustine from pirates and privateers (at the end of the article I will explain the difference between a pirate and a privateer).

The first to attack St. Augustine was the privateer Sir Francis Drake. Though to the Spanish he may have been thought of as a pirate, Sir Drake was indeed a privateer. It was not until the next time the city was sacked that the Castillo was finally authorized by the queen to be built.

In 1586, Sir Drake, with over 20 ships and approximately 2,000 men, sacked and burned the city of St. Augustine. He was only the first.

On May 27, 1586, Sir Drake’s fleet spotted a watch tower on the island of Anastasia, an island which protects St Augustine from the ravages of the Atlantic Ocean. Unaware of any settlements in this area, Drake went ashore to explore. On the inland side they spotted a wooden fort a short distance from a small village. That night a group of men went, in small boats, from the island to the mainland to reconnoiter St. Augustine and the fort.

The soldiers and the villagers fled when they found out the English had landed on Anastasia Island. When Drake’s men arrived they found fourteen brass cannons and a chest with 2,000 pounds sterling in it, pay for the 150 man garrison. The men took twelve of the cannons and the silver. They search the village, but found little of value. Then they set fire to the fort and village. There was a skirmish between Drake’s men and some Spanish snipers, and a few of Drake’s men were killed.

Next came the pirate Robert Searle in 1668, who sometimes also went by the name John Davis. Searle was originally a privateer. But his privateer commission was withdrawn and returned so many times; it is hard to tell if, technically, Searle was a privateer or a pirate at the time of the St. Augustine raid. Searle decided on the St. Augustine raid, in part as revenge for the Spanish sacking of an English settlement in the Bahamas at New Providence, and in part because of the silver the raid would net him.

During the days of Spanish treasure fleets; St. Augustine was a small outpost of the Spanish Realm. It was the last Spanish city the treasure fleets would sight before turning eastward for Spain. St. Augustine had a small garrison of Spanish soldiers to protect the town.

The Royal Treasury in St. Augustine kept the silver used to pay the soldiers of the garrison, and handle transactions for the crown. Occasionally, silver would be delivered to St. Augustine to wait for ships returning to Spain.

It was the silver in the Royal Treasury that English pirate Robert Searle was after. In 1668, he sailed from Jamaica to loot St. Augustine. Searle sailed into St. Augustine harbor in two Spanish ships he had captured. When the harbor pilots did not return from the two ships, those in St. Augustine thought the pilots were merely waiting for better weather, or for the morning before returning to shore. The pirates attacked the city that night. The next morning sixty men, women, and children lay dead in the streets. Searle sailed away with silver and non-Spanish residents of St. Augustine, whom he planned on selling into slavery or holding for ransom. Searle’s men took soundings of the harbor and did not burn St. Augustine, which led many to believe the pirates planned on coming back. The pirates also took every ship in St. Augustine that was seaworthy and all the food and water they could, along with anything else of value.

On his return to Jamaica, Captain Searle was arrested for his raid on St. Augustine and held while the governor of Jamaica waited to hear from England what should be done with Searle. Several months later Searle was freed to take part in Sir Henry Morgan’s famous raid on Panama City. Searle commanded one of Morgan’s ships and was a lieutenant of Morgan’s. Searle distinguished himself during the raid.

Searle would die, years later, in a duel on Honduras. The small sandy inlet where he met his death became known to pirates as “Searle’s Key.”

It was this raid on St. Augustine by Searle that compelled Queen Mariana of Spain to authorize the construction of Castile De San Marcos (the Fort of Saint Mark).

In 1683, came the next pirate attack. But, the pirates lost the element of surprise, and the Spaniards under estimated the size of the pirate force. The pirates moved on, and the city remained on alert, lest the pirates decided to return.

The final pirate attack came in 1686 by the French pirate Michel de Grammont. Grammont was a French nobleman who fled Paris after killing his sister’s suitor in a duel. He arrived in Hispaniola and was commissioned as a privateer.

Grammont’s land attack failed, so he decided to blockade St. Augustine. But, one small ship managed to escape and sail to Cuba for aid. When Grammont found this out, he decided to sail away towards the Carolina’s. It is not known what happened to Michel de Grammont. Shortly after leaving St. Augustine it was rumored that Grammont and his ship were lost in a storm. Neither Grammont nor any of his men were ever heard from again.

Pirate or privateer, what is the difference, and does it really matter? It most certainly mattered to any man who found himself on trial for being a pirate.

A privateer was not a criminal, whereas a pirate was a criminal and could be hanged on capture. Privateers were a part of naval warfare from the 16th to 19th centuries, though they did not take orders from naval authorities. Privateers were private citizens, given a letter of marquee or commission by the crown to raid enemy ships. It was a way for a country to bring more guns to bear against any enemy in time of war, without any cost to the country itself.

There were specific rules a privateer must obey, rules of war for privateers. The man receiving the letter of marquee would have to sign a contract that specified what he was allowed to attack and what he was not allowed to attack. In addition to this, the privateer normally had to pay a bond as well. If a privateer attacked a ship or town not covered by his letter of marquee, he would find himself in court. If it was the judgment of the court, that the attack was due to mistaken identity or some other accident, restitution would be paid to the victim from the bond which had been posted by the privateer. If the court judgment was that the privateer was fully aware of his error before the attack, he was convicted of piracy and hanged. All costs of the privateer were paid for by the privateer or investors. As a reward, they kept a share of anything they captured and could be paid a share of the value of an important ship they sank.

Privateers were required to return to port and have their prizes divided by the court, a share for the country issuing the letter of marquee and the rest for the privateer.

The letters of marquee were usually issued for the duration of the war. Also, privateers were only allowed to attack the property of the enemy countries of the country issuing the letter of marquee.

Attack a ship not at war with your sponsoring country, and you are a pirate forfeiting all the protections the letter of marquee provides. Pirates and privateers did the same thing; the only practical difference was in the targets they attacked. But, muddying the waters even further were the very governments of various countries as well. Quite often, acts of piracy would be over looked against countries not at war, but which had hostile relationships with each other.

A perfect example of this is Spain, England and the island of Jamaica. Even when England and Spain were not at war, they were still somewhat hostile towards each other. It was common in the 17th and 18th centuries for piracy against Spanish possessions to be over looked. Jamaica was a known haven for pirate/privateers who operated against the Spanish. Sometimes these men were even given letters of marquee even though Spain and England were not at war at the time the letter of marquee was issued. This would continue until the Spanish monarch protested loudly to the English monarch. The pirate/privateers would be reigned in, sometimes someone would even be hanged. The Spanish crown would be appeased, and then it would start all over again.

Sir Henry Morgan is famous as a pirate, but technically he was a privateer and not a pirate. Later Morgan became the governor of Jamaica. Sir Francis Drake is sometimes called a pirate as well. But again, his actions were always against the Spanish and covered by a letter of marquee issued by Queen Elizabeth of England.

Many privateers became pirates, and many pirates became privateers. When a war ended, so too did the letter of marquee. All of a sudden the privateer was out of work. This led many privateers to piracy.

At the start of a war countries would be looking to bring as many guns to bear on the enemy as possible, and were quite willing to issue pardons and letters of marquee to pirates.

International treaty officially ended letters of marquee in 1856. But the practice continued in one form or another until almost the end of the 1800s. Some of the most valuable documents of the American Civil War are letters of marquee issued by the Confederacy to privateers during the civil war.

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3 responses to “Pirates, Spies, and Submarines (Part 2 of 2)

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  2. Wow, I learned so much. I didn’t know that the system was so structured. Thanks for a very interesting read Joe!