This study draws upon the labeling perspective to examine whether there are patterns of continuity and/or change in the severity of juvenile court dispositions, and if these patterns vary by race/ethnicity. Using data on youth referred five times to the Pennsylvania Department of Juvenile Justice between 2000 and 2010 (n = 9089), we examine the presence of latent trajectories of sanction severity across referrals, and whether youth with statistically matched criminal/disposition histories, but of different race/ethnicities, receive disparate future dispositions. Results suggest that juvenile dispositional trajectories are more complex than previously reported, largely in alignment with labeling theory predictions (i.e. escalation in sanction severity). However, trajectories representing stability and de-escalation in sanction severity were also identified. Further, certain youth, predominately of minority status, received more severe dispositions over time, despite having similar histories as White youth, supportive of “sticky labels.” Implications for theory and the juvenile justice system are discussed.