Meta-analyses examining the risk factors for recidivism have identified the importance of ties with criminal associates as well as thoughts and attitudes conducive to the continuance of criminal behavior (e.g., criminogenic thinking). Criminologists have theorized that a direct relationship exists between the association with criminal peers and the development of criminogenic thinking. The present study empirically explored the relationship between criminal associates and criminogenic thinking in 595 adult male inmates in the United States. It was hypothesized that the proportion of free time spent with and number of criminal associates would be associated with criminogenic thinking, as measured by two self-report instruments, the Measure of Offender Thinking Styles–Revised (MOTS-R) and the Psychological Inventory of Criminal Thinking Styles (PICTS). Hierarchal linear regression analyses demonstrated that the proportion of free time spent with criminal associates statistically predicted criminogenic thinking when controlling for demographic variables. The implications of these findings on correctional practice (including assessment and intervention) as well as future research are discussed.