Youth police contact is a common experience, rooted in structural inequalities and systemic racism, and research increasingly documents its harmful repercussions. However, scholars have overlooked the connections between youth police contact and subjective perceptions of college aspirations and expectations, an important oversight given that the internalized stigma of police contact can disrupt an individual’s future orientation. In this article, we use data from the Future of Families and Child Wellbeing Study—a longitudinal survey of U.S. children born around the turn of the 21st century in urban areas—to investigate how police contact shapes anticipated unmet educational expectations (i.e., high educational aspirations without high educational expectations), net of youth, family, and neighborhood characteristics associated with police contact. First, youth experiencing police contact with arrests, but not youth experiencing police contact without arrests, are more likely to report anticipated unmet educational expectations than those not experiencing police contact. Second, any police contact—with or without an arrest—is negatively associated with both high educational expectations and high educational aspirations. Third, the association between police contact with arrests and anticipated unmet educational expectations is partially explained by academic performance. Taken together, findings support an accumulating body of knowledge that criminal legal contact, an experience concentrated among youth of color, can hamper youth’s educational outlooks and subjective wellbeing.