There is strong evidence linking skin complexion to negative stereotypes and adverse real-world outcomes. We extend these findings to political ad campaigns, in which skin complexion can be easily manipulated in ways that are difficult to detect. Devising a method to measure how dark a candidate appears in an image, this paper examines how complexion varied with ad content during the 2008 presidential election campaign (study 1). Findings show that darker images were more frequent in negative ads—especially those linking Obama to crime—which aired more frequently as Election Day approached. We then conduct an experiment to document how these darker images can activate stereotypes, and show that a subtle darkness manipulation is sufficient to activate the most negative stereotypes about Blacks—even when the candidate is a famous counter-stereotypical exemplar—Barack Obama (study 2). Further evidence of an evaluative penalty for darker skin comes from an observational study measuring affective responses to depictions of Obama with varying skin complexion, presented via the Affect Misattribution Procedure in the 2008 American National Election Study (study 3). This study demonstrates that darker images are used in a way that complements ad content, and shows that doing so can negatively affect how individuals evaluate candidates and think about politics.