Frequent utilizers of the criminal justice system heavily strain local resources due to their ongoing interactions with criminal justice agencies and their disproportionate need for social and behavioral health services. We first identify and compare frequent utilizers ‘demographic and legal characteristics to first-time and repeat offenders by analyzing two years of prosecution data from three counties in a large Florida jurisdiction. Ordinal regression is then employed to evaluate the impact of first-time offenders, repeat offenders, and frequent utilizers on filed charge severity and the harshness of punitive sanction. Results reveal that frequent utilizers are more likely to be involved in property and drug offenses than personal offenses. They also have an enhanced proclivity to be represented by public defenders or assigned counsel, be held pretrial, and receive custodial sentences. However, contrary to previous research, our findings show that frequent utilizers exhibit a more serious pattern of offending than first-time or repeat offenders. These findings suggest the need for rigorous state monitoring of frequent utilizers in the community while still underscoring the importance and effectiveness of various rehabilitative and prevention strategies beyond the criminal justice system's purview to address the complexities of frequent utilizers’ needs.