The 1865 Morant Bay Rebellion in Jamaica has generally been interpreted as a struggle between the post-emancipation Black peasantry and the white colonial government, which led to a violent confrontation, military suppression, and the demise of the Jamaican House of Assembly in favor of direct Crown Colony rule. Yet, the archival record shows other more complex currents that were also at play, including multi-racial, cross-class alliances, and strong conflicts over local politics, corruption, and labor rights. This article focuses on a little noted aspect of the events of 1865: the arrest for sedition of Sidney Lindo Levien, a Jewish newspaper publisher of The County Union. Levien advocated for the poor, foreigners, and women; joined the Underhill Meetings supporting the political rights of the vast majority of people emancipated from slavery; and was arrested under martial law during the rebellion and later found guilty of sedition, serving nearly 7 months in prison of a 1 year sentence before being pardoned. Drawing on his own writings, photographs, family genealogy, and Levien’s hitherto unknown “Chronicle of 1865,” I argue that his story opens new questions about the relation between Jews and Baptists, Black and “Coloured,” Asian and Maroon, and varied elite and non-elite “White” populations in Jamaica, taking us beyond the typical Black-vs-white framing of the Morant Bay Rebellion toward a more multi-sided emphasis on cross-racial protest and multi-denominational resistance within the imperial global economy. Both dominant “White” colonial histories and subsequent Jamaican “Black” national histories have erased the more diverse actors and cross-cutting interests that shaped the events of 1865, which only come into view through a multi-ethnic history of global mobilities and shifting identities, which I refer to as a critical cosmopolitan perspective.