America won the Spanish-American War… and then realized it had accidentally acquired a global to-do list. In this episode, we zoom in on the messy, controversial aftermath as the U.S. takes control of the Philippines, Cuba, and Puerto Rico—three places with their own histories, hopes, and very different ideas about what "liberation" was supposed to look like. From promises of independence to full-blown insurgency, from benevolent rhetoric to hard-edged occupation, this chapter explores the moment when the United States stepped onto the world stage and discovered that empire is a whole lot more complicated than waving a flag and calling it freedom.