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The global fame of Bad Bunny has raised popular awareness of Puerto Rico and its people, millions of whom live in the United States. In Chicago, the Puerto Rican community has played a pivotal role in shifting understandings of identity and belonging over the past century. This talk will demonstrate how Chicago and the whole Midwest have generated elements of culture and politics that helped pave the way for Bad Bunny's Super Bowl moment, and it will suggest a possible future path for Puerto Ricans and their relationship with the USA.