In this article, we examine our current understanding of adverse childhood experiences (ACEs) and the intersection of mental health challenges and substance use on sexual and non-sexual recidivism. This study uses administrative data and comprehensive case files of a sample of 626 individuals who were incarcerated for a sexual offense. Each case was standardized to a 10-year post-release follow-up time for criminal history review. Findings reveal that ACEs, mental health challenges, and substance use disorder, along with a variety of other factors, affect the pathway to re-offending differently. Interestingly, despite the recent legislative push to utilize one standardized predictor of risk, individuals who commit sexual offenses (ICSOs) had very different re-offending patterns based on historic life events. This research will inform the current legislative debate by providing relevant empirical data on a large sample of ICSOs followed for a substantial period of time.