This paper explores the ways in which male offenders in professional-status occupations prior to conviction construct and justify money-related crime. We report a detailed analysis, based in grounded theory and critical social-psychological discourse analysis, of a loosely-structured group interview with four offenders. The men constructed justifications for their offenses in terms of “breadwinning” for their immediate family and economic responsibility toward their extended “family” of employees and creditors. They represented their post-conviction decline in social status as being “dragged down” by envious “boys” in the state apparatus. They positioned themselves on moral high ground, despite having been inappropriately sent to the working class world of prison (“Dante's Inferno”). We contrast these accounts with those of less privileged male offenders.