Recidivism is a global problem which has persisted over the years irrespective of the kind of punishment to the convicts. For a deeper understanding of the problem, a study conducted on the link between recidivism and punishment was premised to among others analyze progression in criminality by recidivists based on the typology and severity of crimes committed. This study which involved recidivists was conducted at Kamiti Maximum Security Prison and Langata Women prison in Nairobi County. The study purposively selected a sample size of 167males and females from the two prison institutions. Data was collected by use of questionnaires, focus group discussions and key informant interviews. Both quantitative and qualitative techniques were also utilized in data analysis. The study categorized crimes into petty crimes, middle level crimes and felonies. It was established that the severity of crimes increases with reconviction among male recidivists compared to their female counterparts as discussed in detail.