Havana was one of the most important Spanish settlements in the New World. It provided Spanish ships with a protected harbor and served as a perfect port to ready the treasure ships returning from Venezuela, Colombia and Panama for the long return trip to Spain. The operation was a huge endeavor, and it was usually well-known to pirates. Pirates would often gather around the taverns and brothels of Havana and hope to hear rumors concerning the Spanish treasure ships. Spanish colonists would often times reveal classified information on the arrival and departure of the treasure ships to pirates for a price. Many colonists were disenchanted by the strict rules imposed by the Spanish crown that forbade them from conducting trade with merchants not approved by the crown. This kept the majority of the colonists very poor. As a result, the colonists were more than willing to deal with the pirates. If the pirates were successful in their raids of the Spanish ships, they would return to Havana and spend much of their loot in Havana’s marketplace.
In time, attacks on ships leaving Havana became so frequent, that the Spanish armada began patrolling its waters and fortified the city itself. Despite these measures, Havana continued to suffer from frequent pirate attacks until the mid 1700’s.