Winning the Race examines the roots of the serious problems facing black Americans today--poverty, drugs, and high incarceration rates--and contends that none of the commonly accepted reasons can explain the decline of black communities since the end of segregation in the 1960s. Instead, McWhorter posits that a sense of victimhood and alienation that came to the fore during the civil rights era has persisted to the present day in black culture, even though most blacks today have never experienced the racism of the segregation era.

McWhorter traces the effects of this disempowering conception of black identity, from the validation of living permanently on welfare to gansta rap's glorification of irresponsibility and violence as a means of "protest." He discusses particularly specious claims of racism, attacks the destructive posturing of black leaders and the "hip-hop academics," and laments that a successful black person must be faced with charges of "acting white." While acknowledging that racism still exists in America today, McWhorter argues that both blacks and whites must move past blaming racism for every challenge blacks face, and outlines the steps necessary for improving the future of black America.