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While some blame most of the problems of higher education on the neoliberal cutting of taxes, reduced public spending, and corporatization, this paper argues that ideological criticism leaves out the role played by individuals in creating and maintaining a system of gross inequality. In order to comprehend neoliberalism, it is necessary to understand how all of the classic liberal institutions – unions, universities, and the Democratic Party – have been undermined from within. Many liberals are able to escape recognizing their role in neoliberalism by blaming larger social forces; instead, from a psychoanalytic perspective, this paper examines why and how people promote systems that lead to their own oppression. To explain this type of liberal complicity, the theory of obsessional narcissism is developed. Central to this theory is the idea that the more people suffer from lost opportunities and social inequality, the more they seek to become winners in the system that oppresses them. Part of this theory comes from the idea that underlying the narcissistic need for approval from others is a repressed unconscious sense of nothingness or low self-esteem.