This chapter documents the restrictive conditions under which leftwing, “Bolivarian” populism managed to destroy democracy in Latin America. Only Hugo Chavez of Venezuela (1999–2013), Evo Morales of Bolivia (2006–2019), and Rafael Correa of Ecuador (2007–2017) accomplished this feat because they benefited from the high instability plaguing their countries’ presidential systems and, at the same time, from the enormous hydrocarbon revenues provided by the global commodities boom. By distributing massive benefits to ample population sectors, they won overwhelming political support, which they leveraged for dismantling the remaining, already battered checks and balances. By contrast, presidents who did not benefit from such a huge windfall or who governed in countries not suffering from high institutional instability did not manage to still their power hunger and asphyxiate democracy. Instead, some of these leftwing populists suffered irregular evictions from office, whereas others managed to serve out their terms, but failed to perpetuate themselves in power and strangle democracy.