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What does it mean to contextualize legal doctrine and how does contextualization matter? This essay explores a general pedagogy of contextualization within the particular context of a class on race and the death penalty. Teaching the Supreme Court's infamous 1987 opinion in the case of McCleskey v. Kemp within its historical, doctrinal, cultural, and human contexts--rather than as a self-explanatory pronouncement--provides a deeper understanding of America's death penalty system, its connection to America's racial caste system, and the Supreme Court's role in each. These multiple contexts provide a foundation for comprehension and critique of values served by conventional legal methods. They also create conditions for progressive insights about what law enables and what it elides.