Scholarship focusing on barriers to the employment of ex-prisoners has paid little attention to the linkages between mass incarceration and the structural conditions of low wage labor. In contrast, this article considers how decisions to hire ex-prisoners occur in the context of a highly segregated labor market. The research is based upon interviews with employers who are willing to hire persons exiting prisons. These employers were queried about their motivations for hiring, perceptions of their employees with criminal records, and their beliefs about fairness and justice. The interviews show that a strong motivating factor for hiring was finding a “good worker to do a bad job”, but also that decisions were influenced by employers’ common sense norms derived from surviving at the bottom of the economy. Despite the willingness of employers to offer “second chances” and make small allowances, these factors were insufficient to counteract the obstacles to sustainable employment.