The third wave of the Overcoming the Odds longitudinal study involves data about individual and ecological developmental assets and thriving among African American male adolescents in inner-city Detroit gangs (N = 43) or in youth development, community-based organizations (CBO; N = 50). Both groups had comparable levels of either low or high assets across the three waves. Stability in asset levels was not related to either of two measures of thriving or to a second measure of assets. The CBO youth had higher thriving and asset scores. More so for gang youth than CBO youth, there was evidence that asset and thriving scores were interrelated within this wave. Program and policy implications of these group differences are discussed.