Though a self-proclaimed conservative, D'Souza's work often challenges previously established conservative beliefs, especially in subjects such as race. He also challenges liberal beliefs and projects such as affirmative action, and social welfare programs. D'Souza's first and second books, Illiberal Education and The End of Racism, came under critical attack from many liberals. His denial of the existence of institutionalized racism in modern American society have made him an enemy of many civil rights groups and leaders, including Jesse Jackson.
D'Souza has often stated that he believes idealizing the rebellion against slavery is a source of disability among African Americans wanting to re-integrate into the new "non-racist" society. He believes that slaves, to preserve a sense of dignity, in the circumstances of cruel slavery, would by nature tend to be defiant. This defiance, exemplified in the archetype of the "bad nigger", would become the central hero for African slaves, restoring a degree of pride and dignity to all. But, he continues, the price of this would be the habitually engrained attitude of defiance, that was ultimately self-destructive. These self-destructive habits still have a legacy today, and serve to explain, in a large part, the degree to which Slave descendants suffer from social and self-esteem issues, inheritors of an ideal that heralded a bad attitude.
As an Indian immigrant, D'Souza has openly admitted that he believes his race has worked out to his political advantage. As a critic of the role of racism in American society, he frequently denounces the actions of his fellow minorities, often with very frank language that many believe would be perceived as racist if it were spoken by a Caucasian.
He is also a keen observer of many other social issues, and often denounces the notions that Social Darwinism, imperialism, and laissez-faire-conservative ideologies have been complicit in creating many of the world's problems.
His staunch advocacy of preserving individual rights in the face of collectivism and groupism have led some of his conservative critics to argue that his political philosophy is more based along libertarian principles.