This study investigates the relationship between low teacher expectations and principal behavior. The researcher investigated why some teachers seem to acquiesce, or make deals and "give in," to student disengagement. After a two-year ethnographic study in an alternative school for at-risk Black students, the author found that White teachers are more likely than Black teachers to engage in deal-making with students, whereby Black students were allowed to academically and socially disengage. However, another finding of this research was that the school leader--armed with a vision to combat racism and advocate for children--imposed on his staff a policy that required them to socially and academically engage these Black, at-risk students. Implications for school leaders and teachers of at-risk, alternative school children are presented.