Youth living in impoverished urban neighborhoods are at risk for becoming hopeless about their future and engaging in violent behaviors. The current study seeks to examine the longitudinal relationship between social connections, hopelessness trajectories, and subsequent violent behavior across adolescence. Our sample included 723 (49% female) African American youth living in impoverished urban neighborhoods who participated in the Mobile Youth Survey from 1998 through 2006. Using general growth mixture modeling, we found two hopelessness trajectory classes for both boys and girls during middle adolescence: a consistently "low hopelessness class" and an "increasingly hopeless class" with quadratic change. In all classes, youth who reported stronger early adolescent connections to their mothers were less hopeless at age 13. The probability of later adolescent violence with a weapon was higher for boys and was associated with the "increasingly hopeless class" for both boys and girls. Implications for new avenues of research and design of hope-based prevention interventions will be discussed.