Long before Al Qaeda, Mao, or even the Swamp Fox, guerrilla escaped slaves in Jamaica, the Maroons, fought the British army to a standstill in the early 18th century.
The Maroons, who had established themselves in the rugged Jamaican interior after the 1655 British conquest, had long had uneasy relations with the plantations along the shore. They sporadically raided plantations and harbored fugitive slaves.
By the late 1720's, the Maroons had become divided into two groups, the Windward and the Leeward. The Leeward Maroons were led by Cudjoe. While the Windward Maroons were not unified, one of their leaders was Cudjoe's sister, Nanny,.
This low level tension broke out into active hostilities in the mid-1720's, and a large British force arrived in 1728. The Maroons, who were better adapted to in Jamaica's rough, humid, verdant terrain adopted hit and run tactics. The Maroons, masters of camouflage, dressed themselves to look like trees. Their villages were difficult to access; while Maroons could flee to more remote outposts if necessary.
After years of inconclusive warfare, the British signed treaties, first with the Leewards in 1739, and then with the Windwards in 1740.
The Maroons fared less well when, in 1795, a group of them from Trelawny began another war. The British deported these to Nova Scotia.
These Jamaican were by no means the only Maroons. Escaped slaves formed colonies throughout the Americas. Francis Drake and other freebooters would ally with them.