Gun violence poses an enormous problem in Chicago and other large urban areas in the United States, but little is known in the policy or criminology communities about how to deter illegal gun possession and gun violence. This study evaluates the impact of court dispositions on recidivism for individuals whose first contact with the Chicago Police Department was an Unlawful Use of Weapon arrest. I found that the criminal-justice system effectively differentiates between dangerous criminals and low-risk offenders when meting out dispositions, yet despite this accuracy, individuals who do receive a punitive disposition (probation or a jail sentence) are far more likely to reoffend. These individuals receive ineffective sentences and consequently receive insufficient treatment to deter them from future offending. Consequently, I argue that the county maintain judicial discretion for illegal weapon possession cases but establish consistent guidelines for punitive sentencing and introduce innovative approaches to deter recidivism.