Mass incarceration is one of the most pressing issues facing the United States today. While having less than five percent of the world’s population, the U.S. holds more than a quarter of the world’s prisoners. In 2010, California alone held more people in its prisons than any other country in the world outside of Russia and communist China. In response to lawsuits, popular pressures including successful ballot initiatives, and a United States Supreme Court ruling in 2011, the state of California began to dramatically reduce its prison population. This study focuses on activists in South Central working to support and create initiatives that promote decarceration. Data and analysis draws from: 1) auto-biographical experience following long-term incarceration; 2) iterative participant-observation methods with community based organizations (CBOs) (which are part of a longer-term Community Based Participatory Research project on mass incarceration in Los Angeles as a researcher with The Million Dollar Hoods project); 3) audio-visual recorded zoom interviews with key leaders of organizations in Black communities of Los Angeles who have been at the forefront of the push to decarcerate. It explores the ways in which their lived-experience backgrounds play key roles in driving formerly incarcerated people and former gang members into activism on behalf of their communities. The life histories of CBO leaders reveal the systemic routinization of police brutality and the persuasive logics for gang affiliation at an extremely young age that traps them into trajectories of long-term incarceration. They highlighted the life-changing, inspirational effect and cultural capital-building impact of conversion to Islam (or re-discovery of Islam) in jail or prison. The “righteous” ethics, discipline and stability introduced by Islam into their lives foments a desire to work altruistically on behalf of their communities and practically pursue the limited educational opportunities available in carceral facilities. Importantly, most funders fail to recognize the value of the “embodied cultural capital” of gang members and purposefully seek to exclude them while cherry-picking non-gang-affiliated youth to be target service beneficiaries. To be successful, however, programs must recruit active gang members and broker peace treaties with rival factions. Yet, negotiating the bureaucratic requirements to obtain funding requires the cultural capital of a university education which precludes most former and active gang members who would be the best leaders of effective programs from being able to submit fundable projects.