This dissertation studies how people vote and how politicians maximize votes. In the first chapter, I propose non-instrumental benefits to sincere voting as the explanation for why people vote for candidates certain to lose in elections. Building on this idea, I provide a framework where the decision of whether to vote sincerely or strategically is an endogenous choice that responds to election-specific characteristics, rather than a characteristic of a voter. Using both pivotal voter and group rule-utilitarian frameworks, I show that third party vote shares are lower and the extent of strategic voting is higher when the election is expected to be close or when the stakes of the election are high. I also show that adding a heterogeneous non-instrumental sincere voting benefit implies partial strategic desertion of weak parties by their supporters and a lower participation rate for minor party supporters compared to major party supporters. Furthermore, I present theoretical predictions on the impact of electorate size on third party vote shares and on the correlation between third party voting and turnout. Using data from U.S. presidential elections between 1920 and 2012, I also present empirical evidence consistent with the theoretical predictions of this chapter. In the second chapter (joint with Professor Allan Drazen), we ask what the successful electoral strategies are and whether candidates should try to persuade "swing" voters or mobilize their "base". We present a model that can address these and related questions in a single unified framework. We relate electoral strategies to the characteristics of voting groups, with the answers to these questions sometimes being surprising. We show how a candidate may have different ways of winning for given characteristics of the electoral population, with possible "discontinuities" in electoral positions that win elections. We believe that the model we present helps clarify some key issues as well as presenting insights into some real-world experience.