Numerous scholars have offered definitions and perspectives for White people to be or become social justice allies. The purpose of this study was to examine the complicated realities that social justice allies in higher education face when working on campus. Using a critical interpretivist approach grounded in critical race theory, the authors intepret participants constructions of allies and ally work and draw larger implications for these constructions and their capacity to disrupt and uphold systems of oppression and injustice. In examining the experiences of White male faculty and administrators who shared how they constructed and made meaning of the complexities embedded in ally work, we found that participants situated ally work at individual, rather than institutional levels. Findings also revealed the paradox of engaging in ally work, which involved few risks and sacrifices, but greater rewards for being perceived as "good" people. Finally, ally work was viewed as aspirational for the participants. Recommendations for future research and scholarship are offered.