It was previously believed that Cuffee only led a small band of just 43 runaway slaves.Orlando Patterson, The Sociology of Slavery (Kingston: Sangster’s, 1973), p. 272. However, recent research has shown that Cuffee's community counted more than twice that number of runaway slaves. The community was so large that they occupied several makeshift villages in the Cockpit Country. Even though Cuffee was identified by Governor Alexander Lindsay, 6th Earl of Balcarres, as the headman, slave informers told the colonial authorities that Cuffee's community had a revolving headman leadership structure. Michael Siva, After the Treaties: A Social, Economic and Demographic History of Maroon Society in Jamaica, 1739-1842, PhD Dissertation, African-Caribbean Institute of Jamaica library (Southampton: Southampton University, 2018), pp. 183-7.Michael Sivapragasam (2019) "The Second Maroon War: Runaway Slaves fighting on the side of Trelawny Town", Slavery Abolition, DOI: 10.1080/0144039X.2019.1662683 URL Retrieved 10 September 2019. Having secured muskets and ammunition from the Maroons of Cudjoe's Town (Trelawny Town), Cuffee and his men were well-armed and conducted a series of raids on plantations in western Jamaica. They destroyed estates such as Venture, Cox-heath pen, Pantre-Pant and Oxford. Many western planters claimed that their suffering at the hands of Cuffee was worse than what they endured under the Second Maroon War. Armed slaves sent out against them defected and joined Cuffee's community. Jamaican Maroons from Accompong Town tried to subdue Cuffee's community of runaways, but in vain. Michael Siva, After the Treaties, pp. 182-9. URL Sivapragasam (2019) "The Second Maroon War: Runaway Slaves fighting on the side of Trelawny Town", Slavery Abolition, DOI: 10.1080/0144039X.2019.1662683 URL Retrieved 10 September 2019. Eventually, members of the slave "Black Shot" killed two of the revolving headmen, Prince and Hercules, and captured half a dozen runaway slaves. However, Cuffee then withdrew the majority of his community further into the Cockpit Country, and they were never subdued. Michael Siva, After the Treaties, pp. 188-190.Michael Sivapragasam (2019) "The Second Maroon War: Runaway Slaves fighting on the side of Trelawny Town", Slavery Abolition, DOI: 10.1080/0144039X.2019.1662683 URL Retrieved 10 September 2019.
It was previously believed that Cuffee only led a small band of just 43 runaway slaves.Orlando Patterson, The Sociology of Slavery (Kingston: Sangster’s, 1973), p. 272. However, recent research has shown that Cuffee's community counted more than twice that number of runaway slaves. The community was so large that they occupied several makeshift villages in the Cockpit Country. Even though Cuffee was identified by Governor Alexander Lindsay, 6th Earl of Balcarres, as the headman, slave informers told the colonial authorities that Cuffee's community had a revolving headman leadership structure. Having secured muskets and ammunition from the Maroons of Cudjoe's Town (Trelawny Town), Cuffee and his men were well-armed and conducted a series of raids on plantations in western Jamaica. They destroyed estates such as Venture, Cox-heath pen, Pantre-Pant and Oxford. Many western planters claimed that their suffering at the hands of Cuffee was worse than what they endured under the Second Maroon War. Armed slaves sent out against them defected and joined Cuffee's community. Jamaican Maroons from Accompong Town tried to subdue Cuffee's community of runaways, but in vain. Eventually, members of the slave "Black Shot" killed two of the revolving headmen, Prince and Hercules, and captured half a dozen runaway slaves. However, Cuffee then withdrew the majority of his community further into the Cockpit Country, and they were never subdued. 
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Michael Siva, After the Treaties: A Social, Economic and Demographic History of Maroon Society in Jamaica, 1739-1842, PhD Dissertation, African-Caribbean Institute of Jamaica library (Southampton: Southampton University, 2018), pp. 183-7.Michael Sivapragasam (2019) "The Second Maroon War: Runaway Slaves fighting on the side of Trelawny Town", Slavery
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Abolition, DOI: 10.1080/0144039X.2019.1662683 URL Retrieved 10 September 2019.
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Michael Siva, After the Treaties, pp. 182-9. URL Sivapragasam (2019) "The Second Maroon War: Runaway Slaves fighting on the side of Trelawny Town", Slavery
D
Abolition, DOI: 10.1080/0144039X.2019.1662683 URL Retrieved 10 September 2019.
D
Michael Siva, After the Treaties, pp. 188-190.Michael Sivapragasam (2019) "The Second Maroon War: Runaway Slaves fighting on the side of Trelawny Town", Slavery
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Abolition, DOI: 10.1080/0144039X.2019.1662683 URL Retrieved 10 September 2019.