Recent years have witnessed an increase in scholarly and practitioner interest in the effects of toxic forms of leadership and “win or die” organizational cultures in which employees seek to maintain their own status at all costs, yet there is little research examining the interaction of this type of leadership style and organizational culture. In this survey study of working adults, we demonstrate an association between perceptions of toxic leadership and “masculinity contest cultures” (Berdahl, Cooper, Glick, Livingston, & Williams, 2018).norms, rituals, and belief systems valorizing social dominance, work above other parts of life, physical strength, and the avoidance of weakness. Independently, masculinity contest cultures were associated with higher stress, work/life conflict, intention to job search, work engagement and job meaning, while toxic leadership was associated with lower work engagement and job meaning and higher intention to job search. However, results show a slight increase in work engagement and meaningfulness among men (but not women) who viewed their workplace as a masculinity contest and who reported having a toxic leader. These surprising results provide important insights into how toxic cultures retain employees despite their largely detrimental effects on job attitudes and well‐being.