Abstract The painful history of slavery has profoundly affected the identities and social interactions of Afro-Caribbean migrants, whose descendants continue to contend with prejudice and socio-economic marginalization. Andrea Levy's semi-autobiographical novel, The Long Song (2010), traces the turbulent history of Jamaica in the nineteenth century through the lens of Miss Kitty, a character based on Levy's great-great-great grandmother, who was born a slave on the plantation Amity in Saint Catherine's parish. The narrative blends the historical with the fictional and depicts various environmental contexts, inscribed meanings, and human exchanges, including the prominence of social situations perceived through race and class tensions ironically reconstructed through social interactions. Levy boldly broadens the understanding of freedom and subjectivity contested beyond the abolition of slavery.The novel raises compelling issues concerning the construction and negotiation of identity within the context of colonialism, slavery, and the emergent plantation economy in the Caribbean. Levy deals with the notion of identity, an ambiguous term aggregating entangled layers of representational frameworks, contextual meanings, and social negotiations inscribed within the intricacies of cultural encounters. The analysis draws on broadening horizons on identity theory, offering different constructs of identity inscribed within the narrative strands of The Long Song, taking on the complexity of racial stigma, the misrepresentation and projection of black identity through colonial discourse, and the entangled social interactions and exchanges through which identity is constructed and negotiated within contested socio-racial environments.Levy's notion of identity implies a form of social construction performed through the negotiation of increasingly-engaged modes of representation within a complex fabric of social codes, customs, practices, dialects, and worldviews punctuated through the entanglement of one's self and multiple alterities. The precision and nuance of her observation cause the character to realize the "dangerous" assumptions of the English and an awareness of "contested terrain." The negotiation and representation of racialized identity echo an unsettling realization of race triggered by her isolation in the white institution's womb marked by the religious overtone of the day. Kitty contends with the constant projection of her and her fellow slaves' blackness beyond the negative perception construing unreliability, deceitfulness, and brutishness while evoking exoticism and primitivism. The multifaceted engagements with the surround are conveyed through Kitty's subjective first-person narration complemented by different modes of enunciation, including the shifting narration of the slave owner's white wife and the authoritative voice of Ms. Annie, the largely absent historian.