Grounded in critical applied linguistics and linguistic ethnography, this book offers a sustained account of long-term English as a second language (ESL) student resistance at a multilingual public high school in Hawai‘i. This book explores how “oldtimer” students at Tradewinds High contest, disrupt, and inadvertently reproduce institutionally enacted productions of ESL through strategic and often oppositional social practices. Drawing on close ethnographic and interactional analysis, this volume provides detailed accounts of how students mobilize practices such as “doing not learning” and Mock ESL stylization to subvert institutional expectations, while also showing how these practices can recirculate the same ideologies of linguistic legitimacy and social inferiority the students are trying to escape. This volume consolidates two decades of work on the Tradewinds High Study, framing it against developments in linguistic anthropology, raciolinguistics, and critical applied linguistics over the last 20 years. In so doing, Talmy offers a fresh perspective on ESL student resistance, not as disengagement but as organized and dynamic linguistic and cultural production, with particular relevance for understanding long-term English learners and how they enact agency within and against racialized institutional hierarchies. The volume will be valuable reading for students and scholars in applied linguistics, linguistic anthropology, language education, sociolinguistics, and critical discourse analysis.