Comparing data from two ethnographic studies of bilingual teachers and their students in the United States, the authors present a cross-case analysis that illuminates how issues of language are inextricably linked with issues of race, class, and socioeconomic status. The authors show how portraits of teachers' practice help to examine some of the challenges urban, bilingual educators face including questions about teacher identity, bilingual proficiency, networks of support and activist training. Such portraits of bilingual practice shed light on the complexities that include and go beyond language and show the nexus where pluralist and assimilationist goals inform and contradict one another in public schooling. The authors suggest the current political climate places bilingual education at a new and challenging crossroads in the United States with opportunities to re-examine what bilingual education means within specific local and national contexts.