Research examining the factors that precipitate gang membership has contributed substantially to our understanding of gangs and gang-related activity, yet we know little about the factors influencing intentions to rejoin a gang after having being incarcerated. This study examines the relationship between gang characteristics, number of incarcerated friends, and family characteristics and gang reengagement intentions, while controlling for ethnicity. Participants were 206 male serious juvenile offenders interviewed as part of the Pathways to Desistance Study. The model explained between 35% and 47% of variance in gang reengagement intentions. However, only three variables made a unique statistically significant contribution to the model (punishment if gang rules are broken, importance of gang membership, and moral disengagement), with the strongest predictor being importance of gang membership. The results suggest that challenging young offenders’ perceptions about the importance of gang membership might be particularly effective in reducing gang reengagement intentions after incarceration.