Bartholomew Portugues was an early Buccaneer who is well known to have had fortunes which changed like the wind. If Lady Luck was his mistress, than to this particular Buccaneer, she was a fickle one indeed. Portugues was probably not his birth name, assuming that he ever had one. These homeless sea rovers often named each other from the areas of the world they claimed to come from, and Bartholomew was no exception. On his adventures, he seemed to prefer prowling the north coast of Cuba looking for prey that he could easily overcome with his small ship. A ship that carried a mere four cannon, but was crowded with men.
On one
bright, hot day at sea, Bartholomew spied a great galleon on its way to Havana,
from Cartagena. The Spanish vessel
carried 20 cannon and 70 men. It was a prize which Bartholomew's men advised was far
too big to successfully capture.
Dauntless and arrogant, Bartholomew ordered them to attack anyway. History records that "after a long and
dangerous fight" Bartholomew "became master of the great
vessel." He had lost half his men,
which was about 10, and another 4 wounded.
With such casualties, it was unclear how such a vessel might be manned,
but as fate would have it, the few Spaniards that survived readily volunteered
to join his crew. The reason was beneath
the deck. In the hold was 100,000 golden
pieces of eight and 120,000 pounds of cocoa beans. Betraying their country
meant reaping some of the rewards.
The wind wasn't
right for a quick return to Jamaica however, so the successful raiders anchored
near Cape San Antonio, Cuba, where they celebrated, took on fresh water, and
waited for the wind to change. Just as
they lifted anchor again, however, round the cape came 3 Spanish war galleons. Realizing that their galleon had been pirated, the Spanish warships suddenly bore down on the hapless corsairs.
This, unfortunately for Bartholomew, is where
Lady Luck changed her mind.
Bartholomew
Portugues was never terribly admired for his seamanship, and during his
attempted escape from the Spaniards, he dramatically put on an excessive amount
of sail and down crashed the mainmast, leaving his vessel stranded. He and his men, along with the galleon, were
easily taken. Bartholomew's boys and his
Spanish help were all thrown into a seaside dungeon at Campeche. Bartholomew was held on board ship though,
where a gibbet was being erected. The
Spaniards, never feeling much in a merciful mood, planned to hang him straight in
the morning.
This, once
more, is where the winds of his fortune changed yet again. It is told through the historian Esquemeling
that as his jailer fell off to sleep, Bartholomew slipped out the man's knife
and stabbed him to death through the bars, then took the key and unlocked
himself. He was still far out in the bay
however and he couldn't swim. Coming to
the ship stores, he found two wine jugs, poured out the wine, corked them again,
tied them together and used them as floats, whereupon he kicked himself to
safety in the dense mangroves of the coast.
By morning search parties were combing the countryside for him, while
Bartholomew watched gleefully from inside a hollow mangrove tree. After three days, when he saw that the
Spaniards had called off the search he
slipped away through the woods and turned up two weeks later and 120 miles away,
where he came upon a moored vessel and some old shipmates. He told his tale of riches, of his miraculous
escape, and became a captain once again.
It is said
from here that he sailed back with his new crew and captured the very ship he
was held captive on, seizing the prize for a second time. On their way back to Port Royal however (and
after, perhaps, a premature, drunken celebration aboard) he wrecked the ship on
a small island near Southern Cuba, losing the entire cargo. But that was not the end of Bartholomew
Portugues. He would be back again
prowling the coasts, looking for Spanish prey.
Regardless of the fact that vast fortunes slipped in and out of the
Bartholomew's hands, he was said to have died penniless and miserable. 
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