--- - |2 Abstract Gang membership is believed to impede success in the legitimate economic market while simultaneously supporting success in the illegal market. We extend the study of the economic effects of gang membership by using a within‐ and between‐individual analytic design, decomposing gang membership into multiple statuses (i.e., entering a gang, continuously in a gang, leaving a gang, and inactive gang membership), examining legal and illegal earnings simultaneously, and accounting for factors endogenous to gang membership that may contribute to economic achievement. By using panel data from 1,213 individuals who participated in the Pathways to Desistance Study to conduct a multilevel path analysis, we find that active gang membership status is unrelated to legal earnings. Alternatively, entering a gang is associated with increased illegal earnings, attributable to changes in delinquent peers and drug use, whereas leaving a gang has a direct relationship with decreased illegal earnings. Our results indicate that the positive economic effect of gang membership (i.e., illegal earnings and total earnings) is short‐lived and that, on balance, the sum of the gang membership experience does not “pay” in terms of overall earnings. - 'Criminology, Volume 57, Issue 3, Page 452-480, August 2019. '