How can restorative justice, an increasingly common alternative to zero tolerance discipline, serve as an opportunity to both close the racial discipline gap and promote more critical awareness of structural inequality? Using Knight and Wadhwa's (2014) concept of critical restorative justice, I analyzed interviews with youth leaders and staff at one urban charter high school who strove to implement schoolwide restorative justice practices with an explicit lens toward resisting structural oppression and the schools to prison pipeline. Despite evidence of this explicit commitment, participants still tended to favor exclusionary discipline, particularly to maintain order. It may benefit leaders to anticipate the countervailing pressures they will encounter as they try to enact restorative justice practices within districts and communities that are accustomed to punishment and order as markers of 'good' leadership. There also needs to be a greater emphasis on the words and deeds that contribute to 'critical restorative justice,' since restorative justice is so often discussed as a means for reducing the schools to prison pipeline without detailed attention to how it will disrupt traditional patterns of power and discipline in school.