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This Article explores how some of the salient characteristics of classical legal thought influenced the evolution of the Supreme Court's constitutional jurisprudence during the New Deal era. It focuses upon the Court's jurisprudence of economic liberty in the context of substantive due process. Though a similar pattern of evolution occurred in the Court's Commerce Clause jurisprudence, examination of this area of constitutional development is beyond the scope of this Article. Part I provides an overview of legal classicism and its influence upon late nineteenth and early twentieth-century constitutional law. The next Part examines the paradox of legal classicism and its eventual decline. The final Part analyzes the interplay between legal classicism and the evolution of New Deal constitutionalism.