Previous studies have examined patterns of withdrawal from initial teacher education (ITE) programs and have found that pre-service teachers are more likely to withdraw if they are male or older than the typical pre-service teacher. This study presents case studies based on semi-structured interviews with older male pre-service teachers who withdrew from a large one-year post-Bachelor’s ITE program. To better understand the experiences of these pre-service teachers and the reasons they withdrew, we present each case as a unique narrative before examining the similarities and differences in their expectations and why they withdrew from the program. We discuss possible interpretations of and approaches to preventing withdrawal for stakeholders of ITE programs.