When political polarization is high, it may be assumed that citizens will trust the government more when the chief executive shares their own political views. However, evidence is accumulating that important asymmetries may exist between liberals and conservatives (or Democrats and Republicans). We hypothesized that an asymmetry may exist when it comes to individuals’ willingness to trust the government when it is led by the “other side.” In an extensive analysis of several major datasets (including ANES and GSS) over a period of five decades, we find that in the United States, conservatives trust the government more than liberals when the president in office shares their own ideology. Furthermore, liberals are more willing to grant legitimacy to democratic governments led by conservatives than vice versa. A similar asymmetry applies to Republicans compared with Democrats. We discuss implications of this asymmetrical “president-in-power” effect for democratic functioning.