The antecedents of risk taking have been widely tested. However, whether and when leader risk taking influences team-level outcomes is still poorly understood. Drawing from social cognitive theory, this study theorizes that leader risk taking can help team develop two collective regulatory mechanisms: team role breadth self-efficacy (i.e., RBSE) and team moral disengagement. These two regulatory mechanisms then respectively influence team outcomes, including team performance, team organizational citizenship behavior (OCB), and team dysfunctional behavior. Furthermore, we propose that team reflexivity can enhance the positive impact of leader risk taking on both team RBSE and team moral disengagement. Data from a multi-level, multi-source, and multi-wave survey involving 149 teams and 651 employees confirmed that team RBSE and team moral disengagement mediated the impact of leader risk-taking on team performance and dysfunctional behavior. Moreover, team RBSE was found to mediate the relationship between leader risk-taking and team OCB. Additionally, the moderating effect of team reflexivity in the relationship between leader risk taking and team moral disengagement was confirmed. These results underscore the double-edged sword of leader risk taking on team outcomes.