The term "transgender" is used by people whose gender identity or expression falls outside the boundaries of traditional gender expectations. In educational systems, transgender issues are becoming increasingly relevant as both students and staff "come out" as transgender, and as young people explore non-normative gender expression. In comparison to the empirical and theoretical discussions on gay, lesbian, and bisexual youth issues in education, research on transgender youth is sparse, and academic research on transgender teachers is non-existent. Like closeted gay, lesbian, and bisexual teachers, transgender teachers are isolated, hidden, and silent about their authentic identities. This exploratory study offers one transgender-identified teacher's story in an urban public school system. The issues addressed include gender dynamics in the classroom, relationships with students, the connections between sexual orientation and gender identity, and discrimination in the work environment.