The transgressive use of language by out-group speakers, or crossing is used in a variety of ways to achieve both affiliative and disaffiliative ends among youths. However, crossing can also be used as an affiliative resource in asymmetrical power relations between teachers and students. Reporting on the findings of a 1.5 year ethnography of an English/language arts classroom at a multilingual and multiethnic public middle school in Hawai'i, this paper explores one teacher's use of stylization practices which take the form of crossing. The teacher stylizes students' voices through ventriloquizing, which is an affiliative resource when strategically embedded in ritual oppositional frames of interaction. However, when embedded in other interactional frames, this transgressive use of language results in acts of insult or mocking. I analyze audio recordings of naturally occurring interaction to explore how Hawai'i Creole (or Pidgin) is used transgressively in reported speech by the teacher, an "out-group" individual, for negotiating interactions in his English language arts classroom. Instances of transgressive language emerge as artfully performed strategies that provide a rich site for the construction of affiliative identities. The use of crossing allows the teacher to take liminal stances between offense and respect to strategically manage student participation in this diverse classroom. These findings point to the important role that crossing plays in acts of identity through reported speech where the performance of crossing within positively valued, jocular oppositional classroom rituals demonstrates the capacity for crossing as a contributing factor to the emergence of a shared sense of community in the classroom.