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Efforts to redress teacher shortages and increase teacher diversity typically focus on academic support and/or financial assistance. This critical qualitative study, however, shows these efforts must delve further. Herein I pay special attention to Latino boys—-a key demographic in California, where Latinxs represent the largest racial/ethnic group and experience the widest racial mismatch between teachers and students. Using critical studies of race and gender, I examine (1) How do labor processes and racialized masculinities shape Latino boys’ determination to become K-12 educators? and (2) How do Latino boys make sense of their identities vis-à-vis the teaching profession? Findings highlight the importance of resisting gender ideologies to redress teacher shortages, increase diversity, and recruit the next generation of transformative educators.