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Some may consider a 1901 case to be ancient history, but Downes v. Bidwell and its progeny still govern all of these regions. This chapter will explore the Insular Cases as a way to understand the role of race in articulating the relationship between American territorial expansion and American citizenship-between American empire and American democracy. The chapter begins by historicizing the Downes opinion. My aim here is threefold: (1) to provide a brief description of the effects of Spanish colonial rule on Puerto Rico; (2) to set forth the circumstances leading up to the Spanish American War; and (3) to illustrate how the outcome of that war helped to shape America's identity as a colonial power. Next, the chapter tells the story behind the Downes opinion itself, showing how the law reflected an uneasy balance between declaring the island to be both a U.S. possession, and one with a separate, not entirely "American" population. As this story and its aftermath will reveal, Downes and other early cases made clear that Puerto Rico did not enjoy the same status as states when it came to matters of commerce and trade.