This study aims to examine how CEO political ideology influences firm-level outcomes and to identify the contextual conditions under which these effects are amplified or constrained. Prior research grounded in Upper Echelons Theory (UET), reports mixed results regarding how CEOs’ political ideologies influence firm performance, corporate social responsibility (CSR) and strategic risk taking. We conduct a meta-analytic review of 58 studies encompassing a combined sample of 55,847 CEOs, examining the relationship between CEO political ideology and firm-level outcomes. Drawing on imprinting theory, we develop a multilevel framework that explains how ideological imprints are expressed or suppressed by situational enablers and constraints. Our findings indicate that CEO political ideology has statistically meaningful relationships with firm-level outcomes: CEO political conservatism is positively associated with accounting-based firm performance metrics but negatively associated with innovation and CSR. We further offer micro-, meso-, and macro-level moderators, including CEO power, ideological divergence between CEOs and boards, and ideological divergence between CEOs and the national political environment. Our results further show that, among the examined moderators, only CEO–board ideological divergence significantly moderates firm performance. Based on these findings, we discuss theoretical implications and outline directions for future research on CEO political ideology.