Using a mixed method design, this study explored financial knowledge, behaviors, and economic socialization in a sample of men (N = 155) incarcerated in a Midwestern county jail. A financial knowledge assessment, adapted from the FLLIP assessment (Zhan, Anderson, & Scott, 2006), was administered as well as a survey of financial behaviors and criminal history characteristics. Based on responses to the quantitative survey, a theoretical sample of participants (n = 12) was selected to participate in in-depth, qualitative interviews regarding economic socialization to the formal economy, particularly banks. Quantitative analyses revealed that the mean financial knowledge score for the sample was 59%, with Whites (M = .68; n = 46) scoring significantly higher than non-Whites (M = .55; n = 108). Factors related to financial knowledge were explored through bivariate and partial (controlling for age and race) correlational analyses. Hierarchical linear regression was conducted to determine the demographic factors, criminal history characteristics, and financial behaviors that predicted financial knowledge. Results revealed that having filed a tax return was the strongest predictor of financial knowledge. Qualitative analysis, using a grounded theory methodology, revealed that the majority of the men were distrustful of banks and other financial institutions. There appeared to be two pathways to distrust of banks: (1) anti-bank socialization through family and peers, which was solely experienced by the older Black men in the sample and (2) usage problems, which was the predominant pathway for the White men.