Through an investigation into the implementation of Washington D.C.’s Incarceration Reduction Amendment Act (IRAA), this study explores what successful decarceration legislation reveals about the flawed criminal legal system within which it operates and what makes it successful in the face of adversarial structures. Through interviews with key actors in IRAA’s development and implementation, results indicate that the criminal justice system incentivizes prosecutors to keep people incarcerated, lacks restorative justice options for victims, and fails to offer rehabilitative alternatives to incarceration for offenders. IRAA remains successful in the midst of these adversarial structures because local conditions including community networks and receptive judges contributed to IRAA accomplishing its goal of decarceration. Findings suggest that local conditions can be instrumental to the success of progressive legislation operating within an otherwise adversarial criminal legal system. Policy recommendations surround how reform policy can navigate a broken system.