This article offers a novel theoretical account to explain why and when trust relationships within top management teams (TMTs) create strategic benefits. Drawing on Upper Echelon Theory (UET), we propose a moderated-mediation model that shows: (a) TMT psychological safety mediates the effect of TMT cognitive and affective trust on corporate entrepreneurship (CE) (the "why"), and (b) TMTs’ social integration moderates this mediated effect (the "when"). We tested our model within established firms in Ghana. Through a multi-wave survey of 372 members from TMTs representing 124 firms, we first confirmed the effect of TMT trust relationships in CE activities. The results reveal that the two distinct trust dimensions (cognitive and affective trust) among TMTs influence CE, mediated by TMT psychological safety, and this mediated effect is more pronounced when TMT social integration is high rather than low. Our study makes three key contributions to upper echelons research on TMT trust relationships and CE literature. First, it distinguishes between cognitive and affective trust within TMTs and demonstrates how these two distinct dimensions influence CE. Second, it proposes a psychological mechanism (i.e., psychological safety) through which cognitive and affective trust affect CE. Third, it explains when TMT trust potentially yields strategic advantages.