This paper focuses on two cases, both homeless young gay men living—trying to survive—in New York City. The young men's stories and their manner of being in psychotherapy are presented. One, Hispanic, had developed as an angry, aggressive, manipulative anti-authoritarian; the other, African American, was engaging, passive, exploitable, and full of rescue fantasies. The author raises questions about how humiliating childhood physical and sexual abuse and neglect can become woven into character formations of such opposite sorts. The paper concludes with reflections on the technical challenges of working with homeless youth of color in drop-in center circumstances, and some indication of how the therapeutic process had to be adapted to these young people and their situations.