By 1660, only a few years after the English capture Jamaica, Port Royale was a booming center of trade and piracy.
It was in a prime location for tade, and thus quickly became rather wealthy, and was fairly notorious for displaying such wealth quite prominently. Its large habour, wealth, and prime location quickly drew in many pirates. It proved not only to be a perfect spot to spend their treasure, but also a bit of a safe haven and easy launch point to attack nearby Spanish settlement.
The English lacked sufficient troops and eventually got to the point where the Governers would have to rely on the pirates to protect the island and would even hire them to go out and attack French and Spanish ships. By the time 1660 had arrived it had gained a reputation as one of the most corrupt cities in the New World. Most of its population were pirates, prostitues, and knaves. It apparently reached a point where there was about one drinking-house or tavern for ever ten residents. It had become so wealthy that coins were prefered over the usual practice of bartering goods.
However, by 1687 the more upstanding citizens were sick of the city's bad reputation and anti-piracy laws were passed in Jamaica. Soon Port Royale had switched from being so well known as a pirate haven, to being known as a place for execution. 'Gallows Point' was a place were many pirates including such famous ones as Calico Jack were hanged. It is reported that there was one month were fourty-one pirates met their deaths.
In 1692 a devestating Earthquake struck the island and sunk a large portion of the city, killing between 1000 to 3000 people- over half the city's population- afterwhich disease spread like wildfire claiming an additional 2000 lives. Some concidered it Divine Justice or an Act of God which destroyed the city due to its wicked reputation.