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Substantive due process is one of the most cherished and elusive doctrines in American constitutional jurisprudence. The understanding that the Constitution of the United States protects not only specifically enumerated rights, but also broad concepts such as “liberty,” “property,” and “privacy,” forms the foundation for some of the Supreme Court’s most impactful—and controversial—decisions. This thesis explores the constitutional merits and politicizing history of natural rights jurisprudence from its application in Dred Scott v. Sandford to its recent evocation in Obergefell v. Hodges. Indeed, from slavery to same-same sex marriage, substantive due process has played a pivotal role in shaping our nation’s laws and destiny: But was it ever intended to? This paper first examines the legal arguments in favor of substantive due process to determine whether the judiciary was designed to be the “bulwark” of natural as well as clearly scribed law. Then, employing a novel framework to measuring judicial politicization, the thesis tracks the doctrine’s application throughout its most prominent case studies. Often arriving at nuanced conclusions, we observe that the truth is more often painted in some gradation of grey than in black or white.