François L'Olonnais : The Most Savage Privateer of the Caribbean

François L'Olonnais : The Most Savage Privateer of the Caribbean

The golden age of piracy is a treasure trove of swashbuckling tales of lovable rogues scallywags and rapscallions who merrily blew raspberries in the face of the great powers of the time living a life of freedom on the high seas but not today's protagonist the brethren of the coast the legendary self-governed society of buccaneers on the island of tortuga was home to many a legendary scoundrel who braved the waves for the love of booty dreaming about a wealthy retirement but not this guy oh no he was a complete and utter piece of he was an irredeemable criminal and a total psychopath who terrorized the caribbean looting burning killing and torturing whoever came across his path with a particular predilection for spanish colonists his name was francois la oline the most savage pirate of the 17th century. Very little is known about the early years of the boy who became francoise olyny we don't know his exact date of birth only that it was sometime between 1630 and 1635. we know that at birth he was called jean david now and that he was born in the small town of lesab de la in today's vaughan department on the atlantic coast of france and we know that his parents were so poor that they were forced to sell him as an indentured servant when he was 15 years old the teenage john david was whisked off to the other side of the atlantic working first in a sugar plantation in martinique and then under spanish masters in the island of hispaniola this is where modern-day haiti and dominican republic are located for nine long years jean injured a life of back-breaking work in the plantation for little or no compensation he was most likely mistreated and he most likely suffered physical violence i'm only speculating here but it may have been at this time that something snapped inside his mind this is when he may have developed his later sadistic tendencies and his relentless hatred of the spanish by the late 1650s jean david had earned his freedom as per his servitude contract he had the option to become a farmer in hispaniola instead he escaped that community to live among the buccaneers these buccaneers were originally hunters who roamed the wilds of hispaniola they feasted on wild cattle and boar meat prepared in little hearts called bouquets hence their name over time the name buccaneer came to define the pirates and privateers who had found safe haven on the island of tortuga just north of hispaniola buccaneer and 17th century writer alexandra exquemoly described tortuga as common refuge of all sorts of wickedness and the seminary as it were of pirates and thieves this community of scallywags on the high seas became known as the brethren of the coast a sort of independent rogue pirate state with its own laws and even a governor when jean david joined the brethren the governor was won monsieur de la place incidentally the newbie pirate served as a simple mariner on two or three voyages with more experienced buccaneers we have a few specific details on these expeditions except that he developed a reputation for courage and cruelty against the enemy his actions impressed monsieur de la place who gave him a new battle name francois la orlane which simply means the man from alone de la place also gave him command of a ship of his own as a privateer or corsair serving for the french navy today we might be using the terms pirate buccaneer corsair and privateer interchangeably but once upon a time there was a fine distinction a pirate is quite simply an armed robber who works at sea attacking mainly ships and ports a privateer on the other hand is a pirate who has been given authority by a government to attack and pillage ships belonging to other powers the government providing such authorization would receive a percentage of the loot and so the newly minted captain francois la orlane was the blessings of the governor of tortuga and on indirect orders from the french crown set sail on his first independent voyages he would soon become the scourge of the main colonial power of the caribbean the flail of the spanish francoise first raids at sea are not documented but we know that they were successful in later actions lolane proved to be tactically savvy his favorite technique was to take large ships by surprise attacking them with a number of small boats sometimes he would split his forces into two units one group on a larger vessel would engage in a gun battle with new prey while francois himself would lead a surprise raid from canoes attacking the enemy from behind he and his crew became renowned for being both brave and cruel during the early 1660s spanish sailors had been on the receiving end of the cruelty at least when it came to facing francois and his crew but the spanish navy and the spanish armies in the americas were not exactly shrinking violence and sooner or later the empire would strike back in 1667 lolina's ship sank off the coast of campeche on the yucatan peninsula modern-day mexico the corsair and his men disembarked and headed toward the town but fell to a surprise attack prepared by spanish troops the ambush was well prepared and the slaughter was almost entirely one-sided at the end of the battle most of the buccaneers had been killed francois's body lay among the other cadavers smeared in a mixture of caked in blood and sand the spanish soldiers barely gave them a second look before congratulating themselves on the victory but they're just fallen for the oldest trick in the swashbuckler's book playing dead realizing that all was lost while on ed quickly covered his face with the blood of his own superficial wounds and rolled in the sand to make for a more convincing corpse after surviving the massacre the buccaneer bared the body of a spanish soldier dressed in his uniform and left campish he soon ran into a group of slaves whom he convinced to give him a canoe with that flimsy boat the stubborn frenchman made it all the way back to tortuga governor de la place must have choked on his rum when he saw the man of allah once again allegedly back from the dead his escapade may have increased his pirate credentials even further as he was able to recruit a fresh crew with his newly unkillable reputation with a new crew in tow francois set sail on his next objective the spanish town of los chaos on the southern coast of cuba with another ship at his command he had more reason than ever to target his spanish enemies the incursion was spotted by fishermen who alerted the governor in the capital havana the governor sent a 10-gun warship manned by 90 sailors and marines it was more than enough to deal with the meager corsair force he must have been surprised when only one man came back alive the lone survivor brought back terrible news the french buccaneer and his men had succeeded in capturing the spanish warship taking nearly all the men prisoner lana lay had then ordered for them all to have their feet and hands tied the survivors were all made to kneel in a long row the french corsair slowly strolled along the line of captives with a cutlass in his right hand and a sharpening stone in the other the blade of the man from along fell onto the first spanish neck then a second then a third without rush the captain sharpened the edge with his stone and resumed his work when he finally sheathed his cutlass 87 heads had rolled off the bridge of the warship the bloodthirst of the french corsair was motivated by revenge against the spaniards but rage did not exactly obfuscate his cold calculating mind he spared the life of one spanish sailor and sent him back to the governor it was a diabolical move allowing that one witness tale to strike fear into the whole of havana the survivor carried a message from la ollene to the governor i shall never henceforward give quarter to any spaniard whatsoever and i have great hopes. Lolane had upgraded his fleet with the captured spanish warship but he had little loot to speak of after roaming from port to port he eventually attacked and pillaged a ship loaded with gold and silver after this successful heist francois returned to his base in tortuga where he began preparations for his most ambitious plan yet the sack of maracaibo a wealthy spanish colonial town in modern-day venezuela a plan like this needed the right manpower and sola oliney issued a recruitment call over 400 men joined the enterprise including a contingent that was led by mikhail the basque the basque pirate was already retired by now but he decided to return to the fray for one last heist if you like he had been a very skilled infantry officer before becoming a buckner and so he offered to lead actions on land the expedition set sail in late april 1667. during a stop on the northern coast of hispaniola the numbers of the buccaneers increased to 700. la holanne's fleet now fully staffed and stocked on supplies set off to maracaibo on july the 30th 1667. as the fleet was circumnavigating hispaniola olinay spotted a spanish ship just off punta espada and what was lolinae's mission statement well no quarter to the spaniards and no quarter was given setting aside his main objective the french privateer left the bulk of his fleet behind and gave chase to the spanish ship she proved to be a formidable opponent as she was armed with 16 guns the buccaneers were not deterred though and after a battle of three hours the spanish surrendered lolinae discovered that the cargo was worth fighting for the captured ship held 120 000 pounds of cocoa but that was just the entree francois also plundered a huge cache of coins and jewels equivalent to 50 000 spanish dollars of the time our inflation calculator doesn't go back that far but you can consider it an absolutely vast amount of money while francois was raking in such copious booty the remainder of his fleet had not been sitting idle they had captured another spanish ship carrying twelve thousand dollars as well as tons of ammunition and weapons la lanney incorporated the two captured ships into his fleet taking the 16-gun vessel as his flagship with a hold heavy with cash and weapons the buccaneers sailed on to maracaibo in august of 1667 they landed some 18 miles away from the town preparing for a surprise attack but surprise it wasn't as the governor of maracaibo had been warned of the pirates arrival the governor was in charge of the life of 4 000 inhabitants and could count on 800 soldiers maracaibo had been sacked by pirates twice before in 1614 and 1642. that was more than enough and the governor wouldn't let it happen a third time he divided his forces into two units the first would deliver a frontal attack on the invaders while the other would ambush them from the rear what happens next would be funny if it weren't you know horribly violent and tragic so yeah the french pirates who wanted to take maracaibo by surprise and a spanish stealth attack party who wanted to take the pirates by surprise eventually a group of pirates led by mikhail the basque discovered the spanish ambushers and attacked them by surprise the spanish soldiers retreated to the fort of maracaibo located some miles outside of the main town francois michal the basque and their combined raiders besieged the fort for three hours eventually capturing the barracks the whole plan of the governor it was going south some survivors of the ambush party managed to reach maracaibo with news that two thousand pirates were about to pillage the town that's right they said two thousand not the actual seven hundred inevitably panic spread like a plague now considering francoise previous tactic of allowing one survivor to escape one may wonder if the soldiers who spread the panic had actually been set free by the crafty corsair whatever the truth the consequences played in olinay's favor citizens of maracaibo evacuated on mass weakening the defenses of the town grabbing whatever boat they found they quickly sailed to gibraltar not the one in spain but a namesake town on the southeast shore of lake maracaibo with all the resistance gone lollanae and his fleet sailed into the harbor and then marched into maracaibo without a fight as per tradition of the buccaneers lolane's small army divided their loot in equal parts but it was a disappointing booty at this stage consisting only of food and household items lola nade the basque and everyone else wanted the spanish gold but where could they find it they had no idea where the citizens had gone with their valuables the frustrated captains sent 160 of his men into the forests around maracaibo looking for prisoners they returned with 20 soldiers in shackles angela olinay had ways to make them talk francoise unfortunate prisoners were tied up to a wooden rack and subjected to torture loline personally performed his favorite agony inducing methods one of these activities was known as wulding this first consisted of tying a rope around the head of a prisoner by twisting a short wooden stick the rope would tighten its grip similar to the spanish garotte the pressure on the skull and temples of the captives was such that their eyes would eventually pop out of their sockets another basic method was simply to cut out the tongue of the victim certainly it did not help the poor guy talk but it sure motivated his companions to reveal any information that they might be sitting on the last torture worth mentioning consisted of slowly slicing a prisoner to pieces in full view of the others while olinay would start with a small slice first then he gradually increased the size of the cuts eventually hacking off entire limbs eventually somebody talked and revealed that most townsfolk had fled to gibraltar laline led his man to gibraltar carrying out another surprise attack via the swamplands the spanish in gibraltar had been readying some defenses but the majority of their weapons had been left at the fort plus they did not expect an attack on foot from the swamp side of their position at the end of a fierce battle 40 pirates lay dead and 80 wounded the losses on the other side had been much worse 500 dead and an unreported number of wounded who later died of sepsis the hunger of the buccaneers had not been sated by this victory they tortured and raped the survivors looted all their valuables and stole their food many of the remaining spanish starved to death the sack of gibraltar lasted four weeks and then the deranged captain francois laolanae asked for more he knew some spanish refugees had been hiding in the forest and so he sent word to them that he was going to burn the town unless they pay him ten thousand dollars they had two days to comply they finally managed to scrape the some together on the third day as la olanna had already started to set the houses on fire after the sack of gibraltar was over lola nay led the buccaneers back to maracaibo in their first day in town they had not found much to steal but they hadn't played the ransom card yet francoise sent a message to the downtrodden governor asking for thirty thousand dollars to prevent the town from being set on fire after a tense negotiation the french captain settled on twenty thousand dollars and five hundred pieces of cattle laura lennon his crew of rather nasty bastards emerged from lake maracaibo and into the open sea after two months of pillaging burning torturing and killing they had plundered 260 000 as well as gems and luxury goods when they returned to tortuga lolane was probably the most notorious pirate of the caribbean thanks to the newly earned clout and his new riches he was able to prepare a new expedition in 1668 with a force of some 700 men by now the once indentured servant had developed delusions of grandeur he had amassed a fast fortune won almost every battle he had fought conquered two towns so why not conquer a whole country for himself this was the goal of his next expedition taking over the spanish territory of nicaragua the plan of lolino was to make a landing in cape gracias diaz which is spanish for thanks god this cape is the easternmost tip of nicaragua on the caribbean coast and it borders on modern day honduras the corsair fleet however was taken off course by a storm and pushed northward into the gulf of honduras as the pirates waited for the weather and wind to improve they decided to bide their time by pillaging the coast in their cruelty the buccaneers targeted small communities of native fishermen who barely had any possessions besides their cabins and canoes loline and his men burned the natives humble lodgings and stole their canoes effectively destroying their livelihoods for the sake of a very small booty the french captain had sowed hatred amongst the natives they would not forget this and they would spread the word after days of targeting fishermen the pirates moved to strike a more formidable opponent a spanish ship armed with 20 guns moored at puerto de cabals today puerto cortez in honduras the buccaneers were able to quickly seize the ship itself a worthy prey that would make any pirate proud but it wasn't enough for lolina he ordered his men to march inland and conquered the city of san pedro some 50 kilometers or 30 miles south of puerto de caballos the honduran jungle proved to be an emerald hell for both the pirates and their opponents la lannae was frustrated by the constant attacks and ambushes carried out by spanish troops hiding in the forest his men came across two barricaded positions built by the spaniards offering stiff resistance in both occasions they were able to slaughter the garrisons by using rudimentary hand grenades those soldiers who were not killed had a much worse fate captivity and torture this was dictated by the twisted psyche of francois la olines shaw but it also served a purpose the captain had realized that his men were completely encircled by the spanish troops he needed to extract information on their location so as to reach san pedro avoiding further casualties la line interrogated the prisoners taken from the barricades but they would not reveal the positions of their compatriots the pirate went into a rage we don't know if it was a foaming fit or fury or rather a cold-blooded steel-eyed psychopathic malignant anger what we do know are the results francois laline stabbed one of the prisoners in the chest enlarged his wound and then ripped out his heart as the other soldiers stared on in horror the savage pirate bit on the pulsating heart and then he shoved the organ on some poor fellow's face and forced him to eat it he then addressed the other prisoners i will serve you all alike if you show me not another way the remaining captives confessed there was a way out of the spanish encirclement but it would have been very difficult to break it after a further battle the corsair expedition managed to take san pedro but it was a pyrrhic victory their lines had been thinned by the constant harassment from the spaniards and most of the inhabitants had fled with their possessions while in a hats and pedro burned to the ground and then marched his men back to puerto de caballos the buccaneers at this stage were close to mutiny but francois managed to keep up morale by promising a rich loot one of the prisoners had told him about a large spanish ship due to arrive in harbor within three months they waited patiently until she showed up armed to the teeth with 41 guns and 130 sailors laline applied a simple yet effective tactic he targeted the spanish ship with cannon fire from the tallest buildings of puerto de caballo the artillery on board responded to the fire but the spaniards did not notice the four canoes bursting with pirates approaching from the starboard side the corsairs boarded the ship unseen taking the spanish sailors by surprise when they opened the holds of the vessels they were also taken by surprise they weren't full of gold and silver as expected but rather full of paper and steel the disappointment finally broke the crew which splintered into three factions two groups left honduras one returned to tortuga the other went around the caribbean seeking more ships to plunder lolane and 300 men decided to remain in the gulf of honduras but it immediately appeared as though their luck had run out during one of their first outings their ship ran aground on a sandbar for six months olinay and his men were stuck on the coast of honduras trying to free their ship from that trap all the while they had to defend themselves from the incessant attacks of the local tribes bent on revenge after the early raids of lola nay week after week their numbers dwindled until eventually only 150 were left alive francois realized they had no hopes of escaping the sandbar so he had the ship dismantled and he ordered his men to build some barges with their new boats the buccaneers sailed southwards along the coast towards nicaragua but now in a reversal of fate it was the spaniards who gave no quarter chasing lolane away from their territories the buccaneers had no choice but to continue their journey southward in desperate need of food and fresh water all linea and his few surviving pirates landed in the area known as the darian isthmus this was one of the most inhospitable areas of jungle in the world even today considered to be almost impenetrable surrounded by a hostile environment the buccaneers soon run afoul of local tribes most likely belonging to the cuna people some contemporary sources describe the darian natives as inherently violent and cannibalistic however accounts of a later scottish expedition to the darion in 1699 report how the tribes were generally welcoming and especially sympathetic to the enemies of the spanish what we can realistically assume is that the cooner knew about the reputation of la olanne as men for sadistic conquest or perhaps they were simply defending themselves against invaders in any case the kuna soon proved to be more than a match for the pirates gruesome violence after a series of attacks on the corsairs the natives captured the few survivors including the man from milan one of the buccaneers survived captivity with the kunara and was later able to bear witness on the fate of francois laline the locals tore him in pieces throwing his body limb by limb into the fire and his ashes into the air that no trace or memory might remain of such an infamous inhuman creature an infamous inhuman creature indeed monsieur la alinae had gone down in history as the most bloodthirsty of the corsairs of tortuga and probably even of the whole caribbean even though the term is not often associated with pirates the man may have been a psychopathic killer a man completely devoid of empathy who personally killed at least 100 people before we end today i throw the gauntlet of the challenge over to you what pirate in history could possibly rival francois olyny and savagery and cruelty please do let us know in the comments and as always thank you for reading.

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