During the past decade, the construct of political skill has attracted a lot of attention. In particular, its relation to job performance has been examined. With regard to this link, it is typically proposed that political skill affects job performance in a positive linear manner. However, in this article it is suggested that intermediate levels of employees' political skill yield the highest job performance, implying that this association is in fact represented by an inverted U-shape. Findings from two field studies (N1 = 178, N2 = 115 employee-supervisor-colleague triads) that incorporated different sample characteristics (early career employees, established employees), job performance dimensions (overall, task, contextual, and adaptive performance), and rating sources (supervisors and colleagues) supported this idea. Across different analyses, employees with intermediate levels of political skill received higher job performance ratings compared to those with lower and higher levels, respectively. In addition, the nature of the relationships between employees and their raters was found to moderate this curvilinear effect. Specifically, besides the fact that employees who had close working relationships with their raters generally received higher job performance ratings, the decreases in the job performance ratings of employees high in political skill were less pronounced when they had close relationships.