A two-year-long experience tutoring a 9-year-old deprived, illegitimate, black boy whose mother was murdered has been described. He resisted the efforts of a white male tutor, and also the additional efforts of a white female psychoanalyst for a year. Some trial male identifications with entertainment figures were observed during that year, but some significant changes in his relationships and learning occurred after he was encouraged, in the context of a Halloween costume, to identify with a prominent football player, who sent him an autographed photo. During the second year I read to him stories with a highly imaginative and symbolic content which he seemed to grasp. At the end of the time, he was able to use a combination of identification with his tutor and ego ideal in order to embark on a new and apparently frightening experience. In a follow-up, he demonstrated markedly improved reading skills.