This article explores a divide between the affective effects of freedom as a political core concept and its discursive articulation. It analyzes the failure of a Hegelian discourse of freedom that is often articulated in relation to colonial relationships. Departing from the idea of the life-and-death struggle in dialectical thought, the article argues for a different goal for postcolonial thought than dialectic unity as promised in Hegelian philosophy, examining the position of four writers: Alfonso Reyes, Mário de Andrade, F. Scott Fitzgerald, and Ngũgĩ wa Thiong’o. The essay concludes that freedom is not as desirable a political goal as it would appear. First, while logically it is fairly easy to distinguish freedom from coercion, the freedom of self-mastery, and, ultimately, the freedom to impose our own world upon others, affectively, these concepts are in fact often conflated. Second, as Fitzgerald’s The Great Gatsby demonstrates, the promise of dialectic unity is unattainable not only for the colonized or oppressed; it is also beyond the reach of the oppressor. Through the study of other postcolonial authors, the article proposes certain lines of inquiry through which split consciousnesses may offer political alternatives to the use of freedom as a political goal.