In February 2000 the Central Intelligence Agency made public documents detailing a series of clandestine efforts aimed at Fidel Castro, the Cuban revolutionary leader who governed Cuba from 1959. The material, compiled over decades of Cold War confrontation, outlines multiple assassination plots, plans to use biological or chemical agents, proposals to exploit Castro’s public appearances, and cooperation with third parties to remove or discredit him. The declassified records span the 1960s and 1970s—decades in which the United States and Cuba were engaged in intense geopolitical rivalry following the Cuban Revolution and the 1959 overthrow of Fulgencio Batista. The files show that various CIA programs explored a range of methods: poison pills and explosive devices hidden in cigars, contaminated diving gear, and proposals to use pathogens or toxins. Some proposals were highly improvised or speculative; others involved outreach to organized crime figures, Cuban expatriates, and foreign operatives to carry out plots. Not all proposed schemes advanced beyond paper. The documents reveal internal debate within the agency about feasibility and risks, as well as legal, ethical, and political implications. Several plans were rejected, revised, or abandoned. At times operations were curtailed because of concerns about collateral harm, deniability, or the potential diplomatic fallout if attempts were exposed. The declassified material also highlights the role of intermediaries. The CIA engaged with nonstate actors and third-party services to maintain plausible deniability. Those relationships were often informal and poorly documented, making full historical reconstruction difficult. Where links and actions are corroborated in the files, they provide new detail about coordination, funding, and contingency planning, but many aspects remain fragmentary or ambiguous. These revelations prompted renewed debate about U.S. covert-action practices during the Cold War and their legal and moral boundaries. Critics pointed to the ethical problems of plotting political assassinations and using biological agents; defenders argued that such measures—however unattractive—were considered in the context of a global confrontation with the Soviet Union and its allies. The declassification was part of a broader transparency effort that made numerous Cold War-era records available to scholars and the public. Historians caution that while the documents add important primary evidence, they do not represent a fully complete archive. Some records remain classified, redacted, or missing; corroboration with Cuban sources and independent archives is uneven. Consequently, while the files materially expand understanding of CIA planning and intent, they do not settle all questions about which plots moved from planning to execution or about the full extent of outside involvement. For historians and citizens, the released documents offer a clearer, if still incomplete, picture of how the United States’ intelligence apparatus confronted a regional adversary. The disclosures have been used in subsequent scholarship to reassess Cold War-era covert practices and to inform debates about oversight, accountability, and the limits of clandestine action in democratic societies. The documents’ release also reopened public discussion in both the United States and Cuba about the human and political consequences of assassination plots and covert intervention. While Fidel Castro remained in power for decades after many of the plotted attempts, the newly available records contribute to a fuller historical record of confrontations that shaped U.S.-Cuban relations and Cold War policy more broadly.