Puerto Rico’s representative in Washington, Federico Degetau, relentlessly pursued U.S. citizenship from 1900 to 1905. He placed legal claims before judges, lawmakers, the president, and bureaucrats. In the 1901 Insular Cases, the Supreme Court decided that Puerto Rico was part of the United States for one statutory purpose but not for another constitutional one. The most important decision, Downes v. Bidwell, had no majority opinion. Justice Edward Douglass White’s influential concurrence proposed a doctrine of territorial nonincorporation, under which Puerto Rico would receive only fundamental rights and might never be a state. White was skeptical of citizenship for the islanders, whom he saw as inferior. Judicial inaction left lawmakers and bureaucrats to fill the void. Instead, bureaucrats ducked and lawmakers refused to act. Degetau was initially confident that he could embody Puerto Rican merit for U.S. officials. But anti–Puerto Rican racism was bottomless. The labor leader Santiago Iglesias took a pragmatic approach to race and law. He courted the racist American Federation of Labor and sought citizenship not as a font of rights but as an entrée to federal officials.