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Structuring effective interventions targeting youth gang members and those at risk for gang membership is a topic of considerable concern. A major component of evidence-based interventions have been formal process and outcome evaluations. Evaluation activities measure such key constructs as program fidelity, program outcomes, and implementation issues. While many evaluations employ both quantitative and qualitative methods, the primary methodology remains quantitative. Through an examination of a comprehensive, multi-year youth gang prevention and intervention program, we found that intensive participant observation was an necessary element of the evaluation, providing valuable additional context and rich data, that was otherwise unavailable through more traditional methodologies. Furthermore, the use of qualitative methodologies proved invaluable in linking otherwise disparate sources of information. Through regular attendance at program training sessions, the researcher was able to document a number of unintended program outcomes, both positive and negative, and contextualize quantitative data provided the agency charged with administering the program. Our findings demonstrate the importance of regular, unfettered, and intensive participant observation as an essential element of program evaluations of this type. Without the presence of the researcher, a significant quantity of rich data, vital to a comprehensive and contextual evaluation, would have been lost.