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Donald Trump's administration has provoked crisis after crisis regarding the United States' immigration policy, laws, and their enforcement. This has affected millions of immigrants in the U.S. and those hoping to immigrate. Stemming from this, immigration lawyers are providing extraordinary amounts of direct pro bono legal services to immigrants in need. Yet the history of the practice of immigration law has been largely understudied. This article closely examines Chicago's Immigrants' Protective League between 1910 and 1940. The League provided free counsel to tens of thousands of poor immigrants facing a multitude of immigration-related legal issues during a time when Congress passed increasingly strict immigration laws. The League, always headed by women social workers, created a robust model of immigration advocacy at a time when only a handful of women were professionally trained lawyers. The League's archival documents, manifests how Trump's immigration policies have a long and painful history. U.S. immigration law and its enforcement have consistently been cruel, inhumane, arbitrary, and capricious. Told from the ground up and focusing upon the day-to-day problems that immigrants brought to the League, one dramatically sees how immigration laws and practices were like quicksand, thwarting the legitimate expectations of migrants. The League, in response, participated in creating what would become the practice of immigration law, engaging, and quickly responding to changing laws, rules, policies, and the needs of migrants. [ABSTRACT FROM AUTHOR]