This case study examines José, a bilingual Latino fifth-grader, and his complex and dynamic engagements in "travesuras" (mischievous behaviors). José's "travesuras" served to disassociate him from being labeled a "schoolboy." This disassociation was evident in how José: (1) renounced "school-like" work and (2) downplayed his intelligence. José had been pigeonholed--for the most part-- as a smart student who should have known better than to behave inappropriately. Implications point to how to create more nurturing and enriching experiences for urban Latino youth such as José.