The idea that good teachers know the students they teach has long been cherished as an innocent educational value. This study explores this value in a harsh and complex setting which brings together a group teachers and high school students. At this site, the static world of pre-apartheid trained teachers contradicts the dynamic worlds of post- apartheid, street-wise students. At the interface of such complexity teachers'' old ideas, wisdoms, and professional conceptualisations collide with youth from unfamiliar backgrounds. The intensity of educational and pastoral care demanded of teachers mean that they have to contend with sociopolitical changes and harmonise these with educational and psychic demands. The study reveals the intricacies of teachers'' work, and how, the function of teachers- as-knowers is a complex web of uncertainty, stress, and frustration, and yet also a space in which success is necessary, desirable, and possible. The innocence of knowing-as-caring is shattered by evidence that not knowing students might be a viable approach to teaching in adversarial contexts.