Family factors and adolescent life satisfaction have profound effects on later behavior. The present study examined the effects of family cohesion and life satisfaction on internalizing (depression and self-esteem) and externalizing (deviance) outcomes among adolescents. Moreover, this study also viewed internalizing outcomes as conduits that channeled the effects of family cohesion and life satisfaction on later adolescent deviance. Using the Taiwan Youth Project (TYP), results indicated that the family cohesion and life satisfaction of Taiwanese adolescents declined with time, and this, in turn, led to negative life outcomes, such as higher levels of depression and deviance, and lower levels of self-esteem. In addition to the direct relationship between family cohesion and adolescent outcomes, family cohesion also had indirect effects on self-esteem and depression through change in life satisfaction. Also, initial life satisfaction is indirectly related to later deviance through change in family cohesion. Limitations and implications are also discussed.