A critical theory lens is used to explore the role of evaluation in youth development, a field aimed at recognizing youth as assets. A theory of change in the field is questioned for its emphasis on individual youth outcomes as programmatic outcome measures. A review of 209 evaluations of 131 programs in the Harvard Family Research Project’s Out-of-School Time Program Research and Evaluation Database reveals an overemphasis on individual gains related to academic achievement or youth development and a lack of attention to community- or systems-level outcomes. The author posits that a critical approach would press evaluators to be intentional about what they measure and how in order to challenge the status quo for young people. © Wiley Periodicals, Inc., and the American Evaluation Association.