This study investigates why Operation Bootstrap, which once brought industrialization to Puerto Rico and was deemed successful, did not become a sustainable social and economic strategy. The study delves into how Puerto Rico\u27s colonial position affected this shift from success to failure. Although Operation Bootstrap initially prospered due to American funding and technological advancements, Puerto Rico\u27s colonial status ultimately impeded progress. A review of Puerto Rico\u27s history with the United States, including issues of debt and economic development, reveals that the island\u27s colonial past has made it challenging to address concerns related to economic advancement. This essay explores the relationship between the US and Puerto Rico since the Spanish-American War, the triumphs and setbacks of Operation Bootstrap, and how Puerto Rico\u27s colonial history hampered its economic growth. Additionally, it examines opposing viewpoints and underscores the significance of considering Puerto Rico\u27s colonial position when analyzing its struggles
