Pirates of the Spanish Main
Santíago was a much admired spy for the Spanish Royal court, until his penchant for gathering information and his desire for wealth cause him to attempt to blackmail a member of the court, an attempt which backfired badly, and caused him to be wanted by the Spanish Crown. Being fond of his own head, Santíago booked passage on a merchant vessel headed for the Caribbean, where he spent the next several months drifting from crew to crew, sometimes pirate, sometimes simply merchant, taking what jobs he could and trying not to run afoul of any Spanish vessels.
Unfortunately for Santíago, a recent pirate crew he was running with had a run in with a British ship helmed by one Lt Lloyd, and in the ensuing fray, Santíago was captured and imprisoned by the British crew, to meet the fate of hanging when the ship reached its port. So it is perhaps lucky for Santíago that this same ship should become the “acquisition” of Nathaniel Drake and his crew.