The topic of race has long enriched Shakespeare scholarship. Race scholarship remains marginalized in the broader world of Shakespeare studies. The simultaneous “truth” of these statements reveals a deeply rooted professional ambivalence. And while recent attention has been paid to its manifestation at conferences and in journals, this essay explores its challenge to black teacher–scholars in the majority-white classroom. Rethinking The Merchant of Venice as an educational play, with Portia and Shylock performing as nontraditional teachers, I develop the concept of “teacher trouble” from Judith Butler's “gender trouble” to reflect personally on the perils and liberatory potential of antiracist performative strategies.