This article draws from a Cultural Political Economy framework and an abolitionist lens to examine various understandings of safety within Chicago Public Schools (CPS). We investigate how the Chicago Board of Education (BOE) uses convivial rhetoric and institutional mechanisms to erase the demands of Black and Brown students and ultimately reinforce a police-centred notion of safety. We also consider how students challenge this meaning of safety by enacting 'generative safety,' which we understand as rooted in an abolitionist framework that not only rejects policing but also manifests in material reinvestment and centreing the voices of Black and Brown young people.