A path model of hopelessness, belongingness, engagement, and academic achievement was created using variables from Mobile Youth Survey (MYS) data and school records. A sample of 490 African-American students, 49% female and 51% males, were used in data analysis. Sub-samples of 203 stable and 287 transitioning students were used in answering the third research question. Three research questions were addressed (1a) what is the relationship among hopelessness, belongingness, and engagement? (1b) Do hopelessness and belongingness in one year predict hopelessness and belongingness in the subsequent year? (2a) How do hopelessness, belongingness, and engagement affect achievement? (2b) How does achievement affect later hopelessness, belongingness, and achievement? (2c) Does Engagement mediate the relationship between hopelessness and achievement, and between belongingness and achievement? (3) How does the path model of hopelessness, belongingness, engagement, and achievement affect stable versus transitioning students? Analysis was conducted using Structural Equation Modeling (SEM) software. Results indicated that hopelessness negatively affected engagement, as measured by absences. Hopelessness and belongingness directly affected achievement, as measured by reading and math SAT-10 scores, and absences partially mediated the effect of hopelessness on achievement. For the total sample, hopelessness in 2006 predicted hopelessness in 2007, and belongingness in 2006 predicted belongingness in 2007 and hopelessness in 2007. In testing the model with stable students and transitioning students, group differences existed with respect to the significant effect of absences on achievement for transitioning students, the significant relationship between reading achievement and hopelessness for stable students, and the significant cross-effect from hopelessness in 2006 to belongingness in 2007 for transitioning students. A discussion of the results and implications for educational practice and future research follows the findings.