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Latin America is experiencing the longest democratic period in its history, yet power is still heavily concentrated in the executive. In fact, presidents are exercising power to extend their terms and enhance control over elections, often through completely democratic means. This phenomenon challenges our understanding of the relationship between democracy and the rule of law. This dissertation combines institutional and agency approaches to ask why and when presidents gained and exercised power over elections, arguably the most critical component of democracy. I focus on Colombia, Ecuador, and Venezuela, three Andean countries that share certain historic and cultural contexts, yet vary greatly in their democratic development. First, I conceptualize, measure, and analyze the transformation of executive power over elections in formal law, or "institutionalized executive power" (IEP), since transition to democracy (1979 – 2013). Colombia witnessed consistent decline in IEP, Ecuador's trend was mixed, and Venezuela demonstrated an overall increase. Based on qualitative analysis of an original dataset, I argue that institutional factors are the key causal components explaining variation in formal executive powers over elections: configuration (government entities with authority over electoral management, which can be centralized or decentralized); and constraints (restrictions on changing electoral law, which can be weak or strong).The logical next question is how and when presidents exercised their powers. I developed a measure of "exercised executive power" (EEP) over elections and traced presidents' actions over two decades (1993 – 2013). I found that EEP increased over time in all three countries. This was driven largely by political factors, but within the institutional context. I argue that presidents with strong mandates – particularly a majority in the legislature – most often exercised power over elections (and succeeded in their efforts) because of their ability to overcome institutional configuration and constraints. Despite decades of democratization, weak institutions continue to facilitate actions of strong presidents, compromising democratic quality. However, insights from Colombia demonstrate that balance of power among government entities and legal safeguards can temper even the most popular presidents. These findings inform our theoretical understanding of processes that contribute to democratic strength or decline.