Abstract: In 1963, President Kennedy outlined a federal program designed to reduce by half the number of persons in custody in mental hospitals. What followed was the biggest deinstitutionalization this country has ever seen. The historical record is complex and the contributing factors are several, but one simple fact remains: This country has deinstitutionalized before. As we think about reducing mass incarceration today, it may be useful to recall some lessons from the past. After tracing the historical background, this essay explores three potential avenues to reduce mass incarceration: First, improving mental health treatment to inmates and exploring the increased use of medication, on a voluntary basis, as an alternative to incarceration; in a similar vein, increasing the use of GPS monitoring and other biometric monitoring, and moving toward the legalization of lesser controlled substances. Second, encouraging federal leadership to create funding incentives for diversionary programs that would give states a financial motive to move prisoners out of the penitentiary and into community-based programs. Third, encouraging impact litigation of prison overcrowding, as well as documentaries of prison life, as a way to influence the public perception of prisoners. With regard to each of these strategies, however, it is crucial to avoid the further racialization of the prison population and merely transferring prisoners to equally problematic institutions.