This essay provides a rigorous and accessible background to what is likely the most pressing geopolitical issue in twenty-first-century Latin America: the humanitarian crisis in Venezuela under President Nicolás Maduro of the United Socialist Party of Venezuela (PSUV). To this end, it analyzes and connects three distinct political phenomena in Venezuelan history whose interrelated development underpins the country’s current instability: Puntofijismo (1958-1998), Chavismo (1998-2013), and Madurismo (2013-present). It firsts describes the collapse of Puntofijismo, Venezuela’s style of pacted democracy and its oil-dependent petro-state to contextualize the rise of Hugo Chávez’s political project in 1990 known as Bolivarianism. The paper then considers Chávez’s regime and how it continued, yet also departed from, Puntofijismo through clientelism, exclusionary politics, and the creation of an illiberal hybrid regime. Upon this foreground, the paper situates the current student protests, military repression, and humanitarian crisis under President Maduro. Using both English and Spanish-language source material, this paper lays bare the current complex reality that is Venezuela.