A sample of 265 New York City drug court participants completed the Level of Service Inventory—Revised (LSI-R) and Texas Christian University Drug Screen II (TCUDS). Three participant clusters were identified through a person-centered analysis of their LSI-R and TCUDS responses: low risk (LR), criminogenic risk (CR), and complex behavioral health needs (CBHN). Although CBHN scored higher than CR and LR on the LSI-R and TCUDS, they were no more likely to be re-arrested at 24 months and no higher in their rate of positive drug tests. The CR cluster predicted re-arrest beyond the LSI-R and rate of positive drug tests beyond the LSI-R and TCUDS. CBHN participants placed in a residential (vs. non-residential) setting were disproportionately likely to be re-arrested. Results point to a sub-population of drug court participants not captured in variable-centered summary risk scores, who might require intensive case management or referral to suitable treatment.