In the early 18th century, there was something called the Republic of Pirates, it promptly ended when Woodes Roger landed in Nassau and reestablished British rule
https://en.wikipedia.org/wiki/Republic_of_Pirates
The challenge is to create a scenario, with the Republic of Pirates become an independent country, that gains Cuba and Jamaica. How that plays is up to you.
https://en.wikipedia.org/wiki/Republic_of_Pirates
The challenge is to create a scenario, with the Republic of Pirates become an independent country, that gains Cuba and Jamaica. How that plays is up to you.