Bartolomeo Portugues, AKA Bartholomew Portuguese, was another early buccaneer based in Port Royale. He was bold, and ruthless, but plagued by uncommonly bad luck. Taking a small boat with only 30 men, and 4 guns, he prowled the coast of Cuba in search of Spanish ships. When he encountered one it was much larger and well armed than his vessel. He boarded her despite the odds, and he and his were beaten back in bloody hand to hand fighting. Regrouping, the pirates attacked again, and this time overpowered the Spanish. The pirates paid a dear price for the victory, taking over 50% casualties. The plunder was 70,000 PoE, and 120,000 lbs of valuale cacao beans.
Contrary winds made it impossible to sail directly back to Port Royale, so they made for the western end of Cuba. Rounding Cape San Antonio the pirates were suprised and captured by 3 Spanish vessels. The Spaniards released them after taking their loot and cargo. Rounding Cuba to get the wind for a run to Jamaica, they were instead blown into the bay of Campeche, where they tried to put in. The townsfolk recoginized Portugues, as he had previously ravaged the Yucatan coast. He had escaped from them once before, so this time the Spanish kept him locked up on board a ship in the harbor. They began erecting a gallows in town.
Portugues spoke good Spanish, and overheard sailors discussing his fate. One night he killed his gaurd with a stolen knife. He jumped overboard, with two empty, stoppered wine jars for floatation, swam ashore. Then he made his way on foot through 120 miles of wilderness. After a brutal march through jungles, and swamps, with hostile natives, he finally made it to the Eastern tip of the yucatan peninsula. Eventually he flagged down a passing buccaneer ship which agreed to take him to Jamaica.
Eager for revenge, he set out with a conoe, and 20 men. Returning to Campeche, they took the ship on which he had been held. There was no gold aboard, but there was plenty of valuable merchandise. Heading back to Jamaica, the ship ran aground on the Isle of Pines, just south of Cuba. The survivors climbed back aboard the canoe, and returned to Jamaica once again. Then they immediately reequipped, and departed in search of plunder. Esquemelin wrote that Portugues "made many violent attacks on the Spaniards without gaining much profit from marauding, for I saw him dying in the greatest wretchedness in the world.”