Extant research on trust in public administration focuses on trust in a specific level of management, ignoring the connection of trust in different management levels and their effects on employees. Building on the trickle-down and trickle-up models, this study proposes that employee trust in senior leaders fosters their trust in direct supervisors and vice versa. Also, drawing on the job demands-resources model, we argue that trust in senior leaders and direct supervisors indirectly affects extra-role behavior through psychological well-being, and that workload moderates the above effects. Moreover, as leaders and supervisors play complementary roles, we predict that trust in senior leaders and trust in direct supervisors positively interact to enhance psychological well-being. Using the latent moderated structural model with data from the 2019 Federal Employee Viewpoint Survey, we find empirical support for our hypotheses. This study broadens scholarly knowledge about the connection of trust in multi-level managers and their effects on employees’ attitudinal and behavioral outcomes.