This study investigated detained Black youths’ perceptions of racism in public schools and in school discipline. Further examinations included the impact of perceived experiences with racism on externalizing behavior. Semi-structured interviews with five Black youth in a private juvenile justice facility informed these explorations. Of these participants, four were male while one was female. The expected age of participants was between 14 and 17. Coding of interview content involved themes of experiences with racism in schools and school discipline as well as externalizing behavior in response to racism. Relational analyses examined the relationship between externalizing behavior and experiences with racism. Findings revealed consistent themes of perceived experiences with racism, mostly in the form of discrimination from school staff. Themes of racism in school discipline included racial bias in decision-making and excessive discipline. Most participants also reported responding to incidents of perceived racism with externailzing behavior. Externalizing behavior was also directly and indirectly linked to later contact with the juvenile justice system. These findings were supportive of general strain theory, critical race theory, and the school-to-prison pipeline, all of which highlight the impact of racism on externalizing behavior, the presence of racism in school and school discipline, and the contribution of school discipline to being processed by the juvenile justice system.