L’Olonnais first arrived in the Caribbean as an indentured servant during the 1650s. By 1660, his indenture was complete and he began to wander the various islands, before finally arriving in Saint-Domingue and becoming a buccaneer, preying in its vicinity on shipping from the Spanish West Indies and the Main.
A year or two (dates regarding l’Olonnais are at best sketchy) into his piratical career, l’Olonnais was shipwrecked near Campeche, in Mexico. A party of Spanish soldiers attacked l’Olonnais and his crew, killing almost the entire party. L’Olonais himself survived by covering himself in the blood of others and hiding amongst the dead. After the Spaniards departed, l’Olonnais, with the assistance of some slaves, escaped and made his way to Tortuga. Shortly after this, he and his crew held a town hostage, demanding a ransom from its Spanish rulers. The governor of Havana sent a ship to kill l’Olonnais’ party, but l’Olonnais captured and beheaded the entire crew save one, whom he spared so that a message could be delivered to Havana. In the message, l’Olonnais declared: I shall never henceforward give quarter to any Spaniard whatsoever.
The sacking of Maracaibo
In 1667, l’Olonnais sailed from Tortuga with a fleet of eight ships and a crew of six hundred pirates to sack Maracaibo. En route, l’Olonnais crossed paths with a Spanish treasure ship, which he captured, along with its rich cargo of cacao, gemstones and more than 40,000 pieces of eight.
At the time, the entrance to Lake Maracaibo (and thus the city itself) was defended by a fort of sixteen guns that was thought to be impregnable. L’Olonnais approached it from its undefended landward side and took it. He then proceeded to pillage the city, but found that most of the residents had fled and that their gold had been hidden. L’Olonnais’ men tracked down the residents and tortured them until they revealed the location of their possessions. They also seized the fort’s cannon and demolished most of the town’s defense walls to ensure that a hasty retreat was possible.
L’Olonnais himself was an expert torturer, and his techniques included slicing portions of flesh off the victim with a sword, burning them alive, or “woolding”, which involved tying knotted rope around the victim’s head until their eyes were forced out.
Over the following two months, l’Olonnais and his men raped, pillaged and eventually burned much of Maracaibo before moving south to Gibraltar, on the southern shore of Lake Maracaibo. Despite being outnumbered, the pirates slaughtered Gibraltar’s garrison of 500 soldiers and held the city for ransom. Despite the payment of the ransom (20,000 pieces of eight and five hundred cows), l’Olonnais continued to ransack the city, acquiring a total of 260,000 pieces of eight, gems, silverware, silks as well as a number of slaves. The damage l’Olonnais inflicted upon Gibraltar was so great that the city, formerly a major centre for the exportation of cacao, nearly ceased to exist by 1680.
Word of his attack on Maracaibo and Gibraltar reached Tortuga, and l’Olonnais earned a reputation for his ferocity and cruelty and he was given the nickname “Bane of the Spaniards” (French: Fléau des Espagnols). Seven hundred pirates enlisted with him when he mounted his next expedition, this time to the Central American mainland, later that year. After pillaging Puerto Cabello, l’Olonnais was ambushed by a large force of Spanish soldiers en route to San Pedro. Only narrowly escaping with his life, l’Olonnais captured two Spaniards. Exquemelin wrote:
“He drew his cutlass, and with it cut open the breast of one of those poor Spaniards, and pulling out his heart with his sacrilegious hands, began to bite and gnaw it with his teeth, like a ravenous wolf, saying to the rest: I will serve you all alike, if you show me not another way.”
Horrified, the surviving Spaniard showed l’Olonnais a clear route. However, l’Olonnais and the few men still surviving were repelled, and retreated back to their ship. They ran aground on a sandbar in the Gulf of Honduras, and, unable to dislodge their craft, headed inland to find food, but were captured by Kuna’s Tribe in Darién, and he was eaten by the Native Americans. Exquemelin wrote that the natives:
“tore him in pieces alive, throwing his body limb by limb into the fire and his ashes into the air; to the intent no trace nor memory might remain of such an infamous, inhuman creature.”