This essays grapples with the Caribbean basin as a multicultural and cosmopolitan geo-political entity. Locating the Caribbean within and against discourses of European Enlightenment modernity, the essay looks to put forth a cosmo-political ethics of reading that troubles contemporary articulations of cosmopolitanism as fundamentally opposed to discourses of multiculturalism. The essay suggests thinking about a cosmopolitanism from below in which the archipelago of poverty, as Sylvia Wynter has called it, becomes a place where new genres of man proliferate. The unique place of the Caribbean—as extension of Europe, Africa, Asia, and other global geographies and histories, as well as a location where various kinds and types and embodiments of freedom and unfreedom emerge—identifies it as a place where the cosmo-political takes route in all the messiness of ethnicity and raciological thinking. The essay works with the history of ideas produced in and beyond the Caribbean but also influenced by it, in order to encourage different and better conversations about the genres of Man in our troubled times.