This dissertation takes a further step in the analysis of vote buying, exploring two fundamental questions on the causes and consequences of this phenomenon. Namely, why is vote buying more frequent in some Latin American countries than others? And, to what extent does vote buying affect aggregate political outcomes? In contrast to previous studies, my research not only explains how and why the nature of the party system influences the candidates' decision to engage in vote buying in some elections and not others, but also under what conditions voters are more likely to exchange votes for money. Further, I suggest that by engendering this phenomenon at the individual level, inchoate party systems increase the likelihood of electoral fraud, dampening democracy. Results from a multi-methodological research design including a field experiment, archival and survey research, in-depth interviews, and large-N time-series-cross-sectional statistical analysis provide strong support for my hypotheses. As such, my study makes important contributions to the extant literature on clientelism and vote buying, parties and party systems, electoral fraud, and democratization