In 1673 some 200 slaves, most of them referred to as Coromantees, on Major Selby’s estate in St. Ann, killed their master and 13 whites, plundered the estate and the surrounding neighborhood and retreated to secure positions in the mountains on the borders of Clarendon, St. Ann and St. Elizabeth. These groups developed into the Leeward band of Maroon of which Cudjoe was to become the leader.
In July 1690, a large party of 400 slaves on Sutton’s plantation in North Clarendon, most of them from the Gold Coast, rose in rebellion, plundered the neighboring estate, beat back an attack by the troops who had been called out and joined the Leeward Marooons in the mountains. In 1696 another uprising occurred on the estate of Captain Herring. These too later joined up with the Leeward Maroons.
Somewhere about 1720, a Madagascan slave had built up a strong band of followers in nearby Deans Valley, but in a power struggle that followed, the Madagascan was killed and his party was merged into the Leeward group. Shortly after this merge, Cudjoe was elected as their chief and began to pursue a more regular and connected system of warfare and in their frequent skirmishes with the troops sent against them, acquired and art of attack and defense which suited the rough terrain.
Cudjoe was “bear-like” in appearance and often acted in a strange wild manner. Cudjoe, with the help of his two brothers Accompong and Johnny (in the West or Leeward side), and two sub-chiefs Quao and Cuffee (in the East or Windward side), began a campaign of murder and robbery known to history as the First Maroon War. Disguised from head to foot with leaves and cunningly concealed, the Maroons chose to attack from ambush. This form of warfare along with their skill in woodcraft and familiarity with the untracked forests along with their legendary skill as marksman baffled and confounded those sent to fight them. Keen-eyed lookouts would spot an approaching force long before their arrival and spread the warning through the abeng horn, a kind of bugle made from a cow’s horn. Especially skilled horn blowers could use particular calls to summon each member of their party from long distances as if they were face-to-face. The English forces suffered huge losses both from the sharp shooting Maroons and the tropical diseases that were very common at that time.
In 1734 Captain Stoddart lead a successful attack on Nanny Town (named for a Maroon Chieftainess) aided by Mosquito Coast Indians and tracking dogs. The town was completely leveled and to this day is believed haunted by the ghosts of those who died in that battle. Cudjoe, finding himself less secure, moved further into the Trelawny Cockpits and those that escaped the battle moved even further into the Cockpits to establish a new village site. The fighting soon resumed. With a slave to owner ratio of 14:1 and successful new raids on plantations occurring more frequently, the Assembly was sufficiently alarmed to vote the necessary funds for a large scale campaign against the Maroons. The situation was getting desperate for the Maroons as their provision grounds were destroyed and they were forced into smaller areas. The alternative of surrender over starvation was becoming a real option…..but the government did not know this. Shortly after a bloody massacre of English soldiers by a band of Maroons led by Cudjoe from a hiding spot in a cave to be later dubbed the Peace Cave, the King of England in 1738 commissioned Colonel Guthrie to seek out Cudjoe and offer him favorable terms of peace.