Magic, divination, and obeah appear in some form in almost all of Jamaica’s near-continuous revolts from the time the British took the island in 1655 to the decades following the abolition of slavery in 1834. Although discussions of African diasporic spiritual systems were very much alive in the early modern centuries, the forms that emerged in early colonial Jamaica have received little scholarly treatment. This study is an attempt to inject culture into the story of African resistance to slavery and colonialism in Jamaica by reconceptualizing three major rebellions as cultural rather than military histories and by highlighting the role of magic and divination in the genesis of these freedom struggles. The First Maroon War, Tacky’s Revolt, and the 1823 Boxing Day Conspiracy illuminate a clear system of supernatural understanding that came to include a definite link to political resistance and rebellion. These understandings were recognized by enslaved or formerly enslaved Africans as well as the British in Jamaica and abroad. Some work must be done to delineate what European settlers were responding to as the idea of obeah—and how it was related to European ideas about witchcraft and illicit magic—from the ideas held among African peoples. This is especially significant following Tacky’s Revolt, when the first anti-obeah laws in the Caribbean made obeah an explicitly political action. Europeans were clearly wrapped up in the politics of obeah to a degree that did not concern Africans. However, Africans also used obeah as a crucial form of political resistance. Thus, these three cases allow both British and African ideas about obeah to be traced over a century to reinject a cultural history of African-derived spirituality into an otherwise political narrative.