Today, we sit in our living rooms, snacks in our laps, and we watch movies about swashbuckling pirates stealing gold and drinking rum. Our favorite pirate, Jack Sparrow, has wooed the hearts of nautical women all over the world. Although we love the idea of swinging from halyards and clashing swords with Davy Jones, pirates used to be a terror of the settlements along the east coast of present-day America. St. Augustine, Florida was one of the most targeted cities in the new world. After all, the oldest city must have some pretty old riches lying about! While the citizens of St. Augustine feared pirates of any kind, none was more feared than the fearsome team of Captain Thomas Jingle and his most trusted ship steward Andrew Ranson.

Around 1684, Andrew Ranson and a large fleet of ships followed Captain Jingle to St. Augustine from the Bahamas. Jingle had planned an elaborate raid on the city that promised a hefty payout for all involved. Unfortunately, as they approached the city, a huge storm came out of nowhere and sank the majority of Jingle’s ships! Luckily, Jingle and Ranson survived. The captain sent Ranson, along with a crew of six men, to an area just north of St. Augustine where he could restock supplies before they surrendered to the Bahamas once more. Unbeknownst to the pirates, however, was the heavy surveillance of Spanish sentinels that lurked around every corner, waiting to strike on any pirate in the vicinity. Andrew Ranson and his men were captured and brought as prisoners to St. Augustine.

As they entered the city, Governor Juan Marques Cabrera had them all tortured for information on Captain Jingle’s next move. Ranson’s crew held firm loyalty to Captain Jingle, and revealed no information on him. Their loyalty to Ranson wasn’t as strong, however, and they outed him as a pirate to save their own hides. Cabrera was furious, and sentenced Ranson to one of the most gruesome deaths a pirate could suffer: death by garrote. A garrote was a special kind of noose that relied on a twisting handle to increase tension around the neck of the unfortunate pirate, providing a slow and painful strangulation until the release of death. 

Ranson stood with his back to the garrote pole, his shaking hands clutching a rosary as the noose was fitted around his neck. The executioner turned the handle six times, and though Ranson had gone limp, he twisted it a seventh time to ensure his work was done. It was on that seventh turn that the rope snapped, and Ranson fell to the ground in a heap! The city priest, Father Perez de la Mota, rushed forward to the crumpled man to prepare him for eternal rest, only to realize he was still breathing! Andrew Ranson had survived the garrote- a feat that had previously been unheard of. Father Perez took this as a sign from God that Ranson was meant to live, and he brought him to the sanctuary of the church. Governor Cabrera was absolutely livid, and tried to fight with the priest to allow him to execute Ranson once and for all, but Father Perez wouldn’t have it. He continued to protect the condemned life of this pirate for three years until Governor Cabrera was called back to Spain and Governor Don Diego Losada took over running the city. Eager for a compromise, Losada proposed a deal: Ranson would be granted amnesty, so long as he helped with the construction of the Castillo de San Marcos, which still stands proudly today. 

Ranson jumped at the opportunity, and was even granted his full freedom in 1702, when he assisted in defending St. Augustine from an English invasion. Today, he is widely considered the most famous pirate to grace the shores of St. Augustine. There are novels detailing his incredible life, and his name is no stranger to stories told loudly at the stools of beachside bars by old sailors. Although we have thousands of epic tales from the pirates of old, few are more magnificent or legendary than the pirate who dodged an inescapable death.