So, you’ve heard about the dread Pirate Cofresí, the Robin Hood of the Caribbean, infamous raider of merchant shipping and champion of the poor. No one comes from nowhere, so how did Roberto Cofresí, born to a very mundane family, become a scourge of the sea? How did he become an infamous pirate almost a century after the Golden Age of Piracy was over and done with?

As you already know, though he was born to inauspicious parents, Roberto Cofresí grew up in Cabo Rojo, a coastal town in Puerto Rico. Given this location, Roberto encountered sailors all his life and, at some point, decided he wanted to earn his living on the sea. In the early 19th century, Roberto Cofresí purchased a small schooner he named the Mosquito and, it would seem, shortly thereafter chose to become a high seas buccaneer.

During his early days, Roberto focused his attacks nearly exclusively on American shipping. Something of a Spanish patriot, Roberto held no love for American merchants and targeting them garnered him, if not outright protection, at least the apathy of the Spanish authorities. For a time, the Spanish ignored Roberto’s predations, but politics, like all things, rarely stays rests.

By 1824, the Spanish government was looking to get on the good side of the United States and new anti-piracy measures were undertaken. Soon the Pirate Cofresí would find the old apathy gone and that would make his life much more difficult….