The standard class perspectives of democratization claim a strong bourgeoisie and organized working class are more likely to foster democracies than the large peasantry. This dissertation tests this assertion in Haiti and Nicaragua, two large agricultural societies which experienced transitions to democracy in the early 1990s. In Haiti, the peasant-backed movement acceded to power after overthrowing the Duvalier regime, but the movement was overthrown in a bloody coup orchestrated by the bourgeois opposition with the help of the army. Nicaragua experienced a similar crisis roughly around the same period when a popular revolutionary movement finally dislodged the Somoza regime from power. But unlike Haiti, movement actors seized power immediately after the fall of the dictatorship and made gradual concessions to the bourgeois opposition. In February 1990, the movement was defeated after ten years of in power by a coalition of parties. When does peasant-backed movements succeed in building democracies? This dissertation investigates the factors that explain the divergence in the trajectory of the transition in Haiti and Nicaragua. The dissertation shows that transitions in the context of large agricultural societies tended to be complicated by the size of the movement. Large peasant backed movements were naturally predisposed to seek majority rule because such move was consistent with their strategic interests. Large peasant-backed movements were naturally predisposed to seek majority rule because this was consistent with their strategic interests. The dissertation argues that two conditions acted as a kind of antidote against this, the institutionalization of the movement prior the transition and the context of the international environment. Where these conditions were met, sectoral elites tended to make democratic political rather than relying on mass power to impose their will on the opposition. Thus, democracy is not destined to fail where large peasant-backed movements accede to power.