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This article focuses on the inherent similarities between spending power and contract law, and elaborates on Congress’s ability to “contract” with the States, to have States consent to laws beyond Congress’s enumerated powers with federal funding as consideration. A majority of the federal budget is currently spent on social security, social and economic assistance, education, and other aid and development programs. This “contract” thesis permits our system to maintain the virtues of enumerated federal powers. This analogy might suggest a limited role for private parties in enforcing their terms. The article is offered as an illustration for how legal scholarship on constitutional history can perceptively apply legal analysis to improve established concepts to promote freedom, opportunity, fairness, and well-being.