After some years of unofficially sanctioned piracy, Roberto Cofresí found his world changing. The Spanish government which publicly frowned, but privately smiled whenever Cofresí raided American shipping was changing its political views. Spain’s old Latin American empire was largely gone and new European pressures made Spain eager to get on the good side of the rising New World power, the United States. Strangely, the Pirate Cofresí’s most serious troubles came not in Puerto Rico or the United States, but in the modern day Dominican Republic.

Perhaps thinking he could find safe harbor, Robert Cofresí sailed into the new nation of the Dominican Republic, but was quickly arrested by the authorities in Santo Domingo. Sentenced and imprisoned, the Pirate Cofresí did not stay that way very long. He and his men quickly escaped the Torre del Homenaje, fled the Dominican Republic via ship, returned to Puerto Rico in secret, and hijacked a new schooner right under the nose of the authorities hunting him.

Renaming his new ship the Mosquito, the Pirate Cofresí set back to sea to continue his so far successful pirate career. This he would do until 1825 when the Spanish authorities and their temporary American allies became deadly serious about stopping him. Though he had no way of knowing it, in March of 1825 three warships belonging to Spain and the United States marshaled in the waters around Puerto Rico to hunt down the infamous Pirate Cofresí.