This paper examines, through the eyes of Benjamin, a troubled Hispanic high school student in the Bronx, how the character of the school is reflected in the way that it flows around, or evades, its more troubled students. The paper discusses a relatively new school's attempt to understand itself and to define its point of intersection in the life of a child whose values are incompatible with its own. The study began by looking for the processes by which teachers, families, and students with different traditions, values, beliefs, and experiences gain a greater mutual understanding. Observations of and interviews with the student's parents, with teachers at the school, and with the student himself over the year and in various classes provided data for the study. The observations point out the significant mismatch between the student's own aims and those of the high school. Data from the observations showed that knowing the student was part of helping him to be successful, and the school was not a place where a student could hide and still succeed. The school recognized that blurring of the boundaries between the student's life inside and outside of school made for a more powerful form of schooling, though the student felt the effect was too powerful. The school is still searching for ways to bring in students like Benjamin who have behavior problems that jeopardize their success. (SM)