In this article, we analyze the variation in math achievement trajectories of Black male students to understand the different ways these students successfully or unsuccessfully navigate schools and the school characteristics that are associated with their trajectories. Using longitudinal student-level data from a large urban US city (n = 7,039), we analyze Black male students from one cohort to identify trajectories. We find a lack of growth in standardized math scores, suggesting that, on average, math proficiency among Black male students in our sample is declining over time. We found that the 4th-grade standardized math scores of subsidized-lunch students were somewhat lower than those of nonsubsidized students and those of retained students were substantially lower than their counterparts. The average math score of a Black male student's cohort appears to be the only variable amenable to policy manipulation that has a sizeable association with the growth of their standardized math scores, suggesting that putting Black male students in more challenging learning environments may be the best way to increase math proficiency over time. By themselves, other policy decisions (reducing student mobility, teacher turnover, or special education classification; increasing attendance or spending on after-school programming; or hiring more qualified or experienced teachers) all appear to have no or negligible associations with growth in math scores.