This section discusses how the debt crisis has put Puerto Rico’s liminal political status under a microscope and made evident its non-sovereignty. Two court cases whose decisions were meaningful in terms of the Island’s autonomy were the Puerto Rico v. Sánchez Valle case and the Puerto Rico v. Franklin California Tax-Free Trust case. These court decisions had meaningful implications for the Island’s policies on bankruptcy and debt restructuring. The former made clear that the Island is not fully autonomous and ultimately answers to the U.S. Congress; the latter determined that the Island does not have the power to authorize municipalities to seek debt restructuring. These court cases, along with the imposition of The Fiscal Oversight Board, made many wonder whether the United Nations would reconsider its past decisions and recognize that Puerto Rico is, in fact, non-self-governing under international law. These events, which unmasked the Island’s non-sovereignty, were ironically contrasted with the Island’s sporting sovereignty: Mónica Puig won an Olympic gold medal while representing Puerto Rico. In the context of the debt crisis, this victory united Puerto Ricans and allowed them to re-assert their national identity. Furthermore, in this critical moment, Governor Ricardo Rosselló determined that a plebiscite was required to solve the Island’s colonial condition and fiscal crises. Although statehood won, many opposition parties boycotted the election and the validity of the plebiscite was questioned by the federal government.