This paper presents a view of the challenge of working psychodynamically with a child in a school where the staff preferred a more directive approach. Psychodynamic play therapy worked well to resolve the child's presenting problems, but it was too slow and opaque to satisfy the school, which called in a behaviorist consultant. The contrast between the two approaches is presented, along with countertransference issues that arise when two different therapists work with a single patient. Analytic understanding and reflective functioning proved to be useful, both for the child and for the school staff who worked with him.