This study compared the validity of structured versus unstructured risk predictions. Fourteen Juvenile Justice Officers (JJOs) provided 121 risk-need inventory assessments for offending youth under community supervision. Using a rating scale (0-10), another group of 20 JJOs provided estimates of reoffending for a different sample of 107 young offenders. Follow-up data from a few months to approximately 2 years was accessed to identify new convictions. Predictive validity analyses yielded marginally higher, but non-significant, differences in favour of the inventory (area under ROC curve = .75 versus .70). Detection indices improved slightly when reoffending status was determined for a subset of male offenders at 15 months post-assessment. It was noteworthy that when risk scores were converted to categorical ranges (low, medium, high), the distribution was significantly different for the inventory compared with the officers. This was due to more high risk ratings by JJOs compared with more low risk rating from the inventory and highlights one advantage of the latter approach.