Examinations of fraternity life have infrequently analyzed the interconnections between the focus on leadership attitudes and that of members' adherence to masculinities. In this critical quantitative study, the authors sought to comprehend how conforming to gendered norms often associated with historically white masculinities informed relational leadership attitudes for fraternity members. Using data from 3,136 participants in a single national historically white men's social fraternity, results from an ordinary least-squares regression analysis revealed that emotional control, self-reliance, and power over women had negative associations with the relational leadership orientations of fraternity men. Additionally, risk taking and primacy of work had positive associations with a member's relational leadership orientation. Finally, those who identified as queer were less likely to adopt a relational leadership orientation, a result the article unpacks considering the gendered and heteronormative contexts of fraternities. It then provides recommendations for future research, as well as implications for practitioners.