Puerto Rico’s history since 1898, when it became a US territory following the Spanish-American War, mirrors Ireland’s colonial struggles under British rule in several ways. While Ireland endured centuries of occupation and religious segregation, Puerto Rico faced American control marked by economic dependency and suppressed independence movements. Despite differences—such as Ireland’s multiple rebellions versus Puerto Rico’s singular major uprising—both islands share challenges of overpopulation, absentee landownership, restrictive trade policies, and persistent resistance to external rule. This chapter examines the key drivers behind Puerto Rico’s socioeconomic state from 1898 to 1935, drawing parallels with Ireland and other settler colonies, supported by newspaper reports from the New York Times (NYT), Chicago Daily Tribune (CDT), and Los Angeles Times (LAT).