In October 2021, Jacksonville Public Education Fund (JPEF) announced at the start of a new initiative called "1,000 by 2025" with the purpose of recruiting and retaining 1,000 Black and Latino male educators by the year 2025. Given that disproportionalities in student and teacher racial representation continue to persist despite the decades of research that has connected teacher diversity to benefits for all students and that Duval County Public Schools (DCPS) is serving an increasingly racially diverse student population, more work needs to be done to understand the conditions that make it more or less likely for Black and Latino teachers to persist in DCPS. This qualitative study aimed to explore what barriers and motivations may exist for Black and Latino men in the classroom today; and what hopes and concerns they might have for this initiative.