The purpose of this study is to examine the ways in which multilingual learners negotiate identities and ideologies related to educational institutions and to consider how this negotiation relates to their educational investments over time. In particular, this longitudinal qualitative case study explores one multilingual learner’s journey through secondary school and college by analyzing more than six years of data including interviews, a focus group, student work, student records, and participant observation. Informed by critical sociocultural theory, the research examines the social context of education with consideration to the ways race, language, and culture shape and are shaped by educational experiences. Building on Darvin and Norton’s (2015) model of investment at the “intersection of identity, ideology, and capital” (p. 36), the study explores the investment of one student over time and space with particular attention to the ideologies that he negotiates as he works to become his imagined future self. Furthermore, the results prompt educators to consider how multilingual learners’ sustained investments in education can be grounded in ideologies of assimilation for some and ideologies of multilingualism and pluralism for others.