Our research explores how the historically institutionalized and authoritarian discriminatory South African context continues to affect the experiences of LGBT mid-level managers in the workplace. South Africa provides a rich environment to explore “axes of oppression” (heteronormativity/homophobia, race/racism, gender/sexism), and how these manifest and impact on participants’ work experience. Bringing together intersectionality as an analytical strategy with identity work allows us to examine the interaction between identities and the institutionalized processes by which they are shaped. Our findings show a multifaceted fluidity of oppression where individuals can move between continuums of advantage and disadvantage. We demonstrate the importance of historically embedded modes of oppression within the theory of intersectionality and how this manifests in institutional and organizational practices. As a result, organizations, institutions, and individuals play a role in reproducing inequality through intricate systems of oppression at micro, meso, and macro levels. This affects how individuals draw on their intersecting identities to respond to and decipher encounters with others.