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Public-law litigation often gives rise to a basic but important asymmetry: claimants wishing to obtain a particular form of redress for a particular legal wrong must satisfy all the relevant procedural, substantive, and remedial prerequisites to the issuance of judicial relief. In contrast, governments wishing to avoid the issuance of that remedy need only demonstrate that a single such requirement operates in their favor. This Article considers the extent to which this asymmetry influences the development of the law. Specifically, this Article hypothesizes that, where the remediation of a right depends on a claimant’s satisfaction of multiple, mutually necessary procedural, substantive, and remedial rules, it will often be easier for courts to achieve and maintain decisions that frustrate the vindication of that right (and thus move the law in an “entitlement-weakening” direction) than to achieve and maintain judicial decisions that promote the vindication of that right (and thus move the law in an “entitlement-strengthening” direction). “Entitlement-strengthening” initiatives, after all, can often be undone by a single, counteractive change to any one of the several rules on which a claimant’s vindication of the right depends. “Entitlement-weakening” initiatives, by contrast, will often be immune to such a simple counterattack. Consequently, an “asymmetric entrenchment of entitlements” is hardwired into the basic architecture of public-law doctrine, rendering “entitlement-strengthening” decisions consistently more vulnerable to down-the-road retrenchment than their “entitlement-weakening” counterparts.