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This paper follows the 22-year journey of a small community-based program with roots in a psychoanalytic training institute, to the program's current status as an independent non-profit organization serving families throughout the Bronx with psychodynamic, attachment-based parent-infant treatment. The product of an unusual collaboration among a psychoanalytic training institute, a program of the NYC Department of Education and several generous foundations, we aimed to offer teen mothers a dyadic model of parent-infant intervention based on the principles of psychodynamic theory, attachment theory, and mentalization through the lens of an infant mental health perspective. Underlying the creation, implementation, and expansion of the Chances for Children organization at every level were questions of basic trust and mistrust, class, and culture. With this in mind, we describe the development of the model, collaborations with institutions and communities, and the obstacles we encountered along the way. On a macro level, we consider questions of class, culture, and institution that we encountered on every level in institutional bureaucracy, in community outreach, and in collaborating programs. On a more micro level, we use the contexts of a teen-parent therapeutic group and a dyadic mother-child treatment to address issues that arise when white, middle-class clinicians of privilege work in communities of color that are frequently suffering insufficiencies in food, housing, jobs, and experiencing random violence. Finally, we reflect on what has made the work of Chances for Children possible, successful, and enduring even as we embarked on the telehealth practices necessary during the COVID pandemic.