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Laventry's engagement present to Cecilia was no less than the main tobacco plantation in Tortuga, on the east side of the island. Apparently, daring to propose to his first love after so many years had brought him an incredible lucky strike. And he thought it just fair to share it with her.

While Laurens de Graaf and his lot lingered looting in the Gulf of Campeche, Laventry decided to try a whole different course. So he organized those who had stayed back and set sail to the southwest once more. Knowing the Spaniards were still struggling to rebuild their defenses after his attack two years earlier, he led his fleet past San Carlos castle and into the Lake of Maracaibo like he owned the land. And when the Spaniards tried to stop them, they took the castle again and head south. They fired their cannons as they sailed past Maracaibo port, just to scare the good citizens and greet the kind harbor women. When they raised the end of the lake, Laventry spread his ships outside Gibraltar harbor. And they took the city that night.

Despite L'Olonnais' and Morgan's vicious takeovers in the past, the local production of cacao, plus the tobacco and other raw materials coming from the southern mountains, made Gibraltar an active trade harbor. The pirates gathered enough plunder to call it a day and didn't bother to ask for a ransom to liberate the city, like they'd done in Maracaibo not two years earlier. They lingered in Gibraltar for a couple of days. And before the Spaniards sent from Cartagena and other cities to expel them could even sight the city, Laventry and his fleet took their leave. They sailed past San Carlos castle uncontested and decided to visit Coro, on the opposite shore of the lake.

Laventry commanded the landing party, leaving Harry to lead their ships around the peninsula and meet them at the other side. Laventry's party walked the ten miles from coast to coast, looting on whatever they found. They reached their ships without any serious incident and sailed east. Before heading back home, they decided Margarita Island was worth a visit. Staying away from the Pampatar cannons, Laventry led his men to land on the northern side of the island, pillage whatever wasn't stuck to the ground and set fire to the rest.

Then Laventry deemed it was time to head back home. But his good luck refused to leave him be. On their way north, they caught sight of the Indias Fleet, some twenty-five merchantmen coming from Spain with their holds overflowing valuable goods. The convoy had just finished their first stop in San Juan and sailed to the Spanish Main.

Against their usual strategy, the two escort galleons didn't sail together at the rear. Maybe they'd been warned in Puerto Rico about the pirate fleet roaming in the southern Caribbean, and that was why the largest galleon, the Concepcion, was sailing ahead of the formation.

Wise and realistic, Laventry stopped his men from scattering apart and attack the merchantman at random. He only allowed actions against the rear galleon and a few merchantmen struggling to not fall behind. He split his fleet in two, sent the larger ships against those merchantmen and left the smaller ships to take on the galleon. That maneuver, which looked suicidal at best, turned out to be masterful: the galleon's hundred guns could nothing against the swarm of sloops that surrounded her, so small compared to that floating fortress that only the guns on her bottom deck could harm them.

By the time the Spaniards understood the trap, it was too late. The pirates captured the galleon and the three merchantmen, sent the prisoners away in boats and resumed their course north with their four prizes.

Laventry led the fleet to Mona Island, were they distributed the plunder, and then headed to Puerto Plata, causing massive panic among the population. But while the citizens fled to the south, fearing Laventry would wreck the place again, the smugglers hurried to the harbor to greet the pirates. And they didn't hesitate to invest even their last coin to buy so much valuable goods. Hardly any of it ever arrived on ships with the Burgundy Cross, and they knew they would sell all of it for three times the price among the needy population.

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