The purpose of this longitudinal, embedded quasi-experimental mixed methods study was to explore the affect, self-identity, and behavioral patterns of youth adjudicated into a secure facility for their illegal sexual behaviors. Through a partnership with a secure facility and a community organization, the study examined intake and exit measure scores from the Millon Adolescent Clinical Inventory (MACI) and Psychopathy Checklist: Youth Version (PCL: YV) for 137 youth adjudicated for their illegal sexual behaviors in order to compare differences between those who participated in a creative writing class and those who did not. Furthermore, for those who participated in the creative writing class, their published poetry served as qualitative data analyzed for emotional expression. Finally, the two sets of data were “mixed” to determine whether there was a correlation between the types of emotions expressed and scores on outcomes of the two measures. The findings established that there were not great differences in outcome scores on the MACI and PCL: YV between those who participated in the creative writing class and those who did not. This was not surprising given that the creative writing class is an adjunct to the central therapeutic interventions available within the secure facility. However, those who did participate in a creative writing class had greater decreases in self-reported oppositional behaviors, while those who did not had greater decreases in suicidal tendencies and depressive affect. Next, regarding the poetry, a larger number of negative emotions were interpreted than positive emotions, but a full range of emotions was expressed through topics of grief, love, abuse, self-exploration, and various other topics. Finally, when assessing the correlation between the number of Positive or Negative Emotions interpreted and exit scores on the MACI and PCL: YV, there were significant correlations for the subscales on the MACI but not the sum score of the PCL: YV. The results of this study may encourage the inclusion of the arts in secure facilities and research contexts.