Changes in electoral markets in the late 20th century have forced political parties to adapt. Having lost much support and facing growing disaffection, parties often resorted to organizational structure reforms as means to reengage with a dealigned electorate. This article explores the impact of two changes in party organization—democratization of leadership selection procedures and increasing leadership power—on the extent to which leaders have an effect on voting behavior. In doing so, it analyzes the understudied interconnection between the electoral and the party faces of the presidentialization of politics thesis. The results provide mixed evidence regarding the relationship between both dimensions of presidentialization: more leadership power boosts leader effects, but only non-divisive direct leadership elections favor leader effects. This is a comparative study on Western democracies, combining individual-level data from the Comparative of Study of Electoral Systems with contextual data from the Political Party Database Project.