Objectives: While the economic model of crime suggests that improving post-prison labor market prospects should reduce recidivism, evaluations of previous employment-oriented re-entry programs have mixed results, possibly due to the multi-faceted challenges facing prisoners at the time of their release. We present an evaluation of an experiment that combines enhanced employment opportunities with wrap around services before and after release. Methods: This paper presents what we believe is the first randomized controlled trial (RCT) of a re-entry program that combines post-release subsidized work with “reach-in” social services provided prior to release. The sample was 236 high-risk offenders in Milwaukee with a history of violence or gang involvement. Results: We observe increased employment rates and earnings during the period when ex-offenders are eligible for subsidized jobs, and these gains persist throughout the year. The intervention has significant effects (p < 0.01) in reducing the likelihood of rearrest. The likelihood that the treatment group is re-imprisoned during the first year after release is lower than for controls (22 vs. 26 %) but the difference is not statistically significantly different from zero. Conclusions: The results of our RCT suggest that “reach-in” services to help improve human capital of inmates prior to release, together with wrap around services following release, boosts employment and earnings, although whether there is sufficient impact on recidivism for the intervention to pass a benefit-cost test is more uncertain. Average earnings for both treatment and control groups were very low; legal work simply does not seem that important in the economic lives of released prisoners.