This multi case study examined how leaders of color narrated their experiences regarding access to leadership positions at two universities in California before and after Proposition 209 (California's anti-affirmative action legislation) was enacted in 1996. The research focused on addressing a gap in the literature with regards to professionals of color and the barriers they may have faced in the hiring process in an era of anti-affirmative action legislation. Semi-structured interviews of eighteen Student Affairs leaders of color (with job descriptions no lower than assistant director) were conducted. In addition, critical discourse analysis as outlined by Fairclough (1995) was used to analyze affirmative action plans from both institutions before and after Proposition 209. Cultural capital and critical race theory were the theoretical frameworks used to analyze the participant narratives and the discourse within the affirmative action plans. Findings included: qualifications being more important than cultural forms of knowledge, more diversity among director level positions, the hiring process being described as complex and lengthy, the importance of professional mentors, and leaders of color needing to assimilate to valued norms representative of the status quo to be successful in the hiring process as well as in their professional work environments. Recommendations for further research as well as recommendations for leadership development for professionals of color in higher education institutions is discussed.