Ahrrrrrrrrr ! Pirates in Cartagena

All of these pirates attacked Cartagena.
Left to right, top to bottom: Francis Drake, Generic Pirate, Giovanni da Verrazzano, Jean François de la Roque de Roberval, John Hawkins, Monkey D. Luffy.

The first pirates to attack the Spanish Empire did so under French Corsair patent: the Italian navigator Bernardo da Verrazzano (a.k.a. Juan Florian, apparently just the same Giovanni da Verrazzano, also Italian, who first explored the lands between Newfoundland and Georgia, and christened the islands now forming the state of Rhode Island - periods of activity are apparently compatible) in 1521 intercepted a Spanish flotilla, en route to Spain with the Monteczuma treasure, and managed to take a considerable part of it back to La Rochelle.

La Rochelle under siege by Richelieu (1627). Probably not its happiest moment.

The first pirate to enter Cartagena, in 1544, was the French aristocrat Robert Ovalle, or Roberto Baal, actually Jean François de la Roque de Roberval, who stole into the city in the early morning of "dia de Santiago" (25 of July), and managed to obtain a ransom of 200k pesos after threatening to burn the city to the ground (Cartago Delenda Est !).

Cartago deleta est. I.e. don't fuck with the Romans.

The French apparently loved the climate in Cartagena (well, try to outlive a winter in Paris..), as in 1559 Martin Coté and his beloved brother Jean de Beautemps attacked head first the city with 1000 something veteran pirates, managed to get control of Getsemanì, a strategically placed island right on the side of the historical centre of Cartagena which just everyone used as a base to force the town to its knees, and forced the town to its knees. Ransom and all. Usual story.

No, not this Gethsemane,

Cunning was the weapon of choice for the 1568 attack by John Hawkins, who placidly attempted to inconspicuously dock in Cartagena with his fleet in order to sack it, as he had done in other Spanish ports of the Caribbeans. Sadly, the governor of Cartagena decided to welcome him with a shower of cannon balls, poison arrows and arquebus shots. Hawkins got away with hide and everything, played the pirate gentleman for a while longer and died off the coast of Puerto Rico twenty seven years later.

After the French and the English, Dutch pirates, which were known as Watergeusen or Zeegeusen - apparently and appendix of the Geuzen movement, a calvinist and aristocratic enterprise which opposed Spanish domination in the Netherlands - began raiding the Caribbean.

The Geusen emblem even has the tetragrammaton on it !

The first pirate age was concluded with Francis Drake's attack on Cartagena in 1586, who began playing the corsair after escaping a great purge of pirates by the Spanish in 1579 - which he accomplished by sailing beyond Cape Horn and attacking the Spanish colonies on the Pacific - and accomplishing for the second time in history a circumnavigation of the world.
Cartagena went all out to get rid of him, and even the pious Franciscan and Dominican friars took arms to fight the invader, allegedly singing and praying all the time, but Drake, probably annoyed by the constant chanting, was relentless, captured the city, got helluvalot pieces-of-eight as a ransom, and was gone in a cloud of dust. Or a spray of surf. Choose your own adventure !

While Drake's life was by no means a dry one, he died of dysentery in 1596.

Francis in Cartagena. He managed a 500+k pieces-of-eight ransom. Pas mal.

(P.S.: Other pirates did follow ! However, I'm lazy)