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Abstract: This essay identifies and diagnoses the problem of political persistence in the context of the contemporary American state, a phenomenon that extends beyond the “dead hand” problem first articulated by Thomas Jefferson and developed in his correspondence with James Madison. Jefferson’s critique of intergenerational binding, rooted in his belief that present generations should not be constrained by the decisions of their predecessors, clashed with Madison’s emphasis on stability and the practical needs of good governance. While this debate framed the American Constitution’s approach to change—enshrining an arduous amendment process and generally encumbering collective political action—the challenges of intergenerational democracy have deepened over time. We argue that these challenges are not limited to questions about constitutional endurance or rigidity but are compounded by salient dynamics of political development. Specifically, we identify three phenomena—path dependence, institutional thickening, and kludgeocracy—that constrain the ability of present majorities to enact meaningful political change by fundamentally constraining the agenda, reducing the range of viable alternatives, and narrowing the scope of democratic agency. Situating the Jefferson-Madison debate within broader developmental context, we reveal how the historical construction of politics subverts democratic empowerment and affects a democratic deficit distinct from conventional accounts of the dead hand.