How should a constitutional democracy distribute rights, opportunities, and burdens when inherited inequalities persist across generations, but living individuals are not identical to the historical agents or institutions that generated them? This essay addresses this problem through India's postcolonial democratic, legal, and economic transformation. It develops an analytical framework that differentiates between historical injustice, transmitted advantage or disadvantage, contemporary structural disadvantage, and individual circumstance. Moving beyond a simple opposition between methodological individualism and structural analysis, the essay defines reflexive democratic fairness as a multidimensional practice distinct from, but complementary to, institutionalized distributive and corrective justice. It argues that claims for contemporary distributive intervention are strongest when historical injustice has demonstrable and continuing structural consequences, rather than being based upon ancestral moral liability alone. The essay also examines how precolonial Indian formations—heterogeneous, regional, and institutionally layered—were transformed through colonial enumeration, administrative classification, and modern state institutions. The framework is formalized through three core normative principles (Moral Separation, Epistemic Discipline, and Proportionality) and six operational policy tests (Targeting Precision, Causal-Mechanism Verification, Proportionality Calibration, Democratic Reviewability, Epistemic Reflexivity, and Non-Essentialization). Using affirmative action, the Economically Weaker Sections (EWS) reservation, and colonial reparations as test cases, the essay argues that historically grounded policies require continuing scrutiny against empirical evidence, institutional purpose, and the dynamic relationship between historical structures and present circumstances.