PurposeThis study examines the early criminal careers of organized crime offenders in Italy and the Netherlands and assess how these behaviors have evolved across generations. We (1) compare the early careers with the entire career in the two country samples and (2) assess the influence of generational shifts and social changes on these behaviors, particularly focusing on crime control policies. MethodsAnalyzing data on male offenders born between 1950 and 1986, we analyze criminal careers up to ages 23 and 30. Our analysis includes statistical assessments of differences between countries and among decades, employing multinomial logistic regressions to explore the associations between criminal career parameters and crime categories and the offenders' decade of birth. ResultsSignificant differences were found between the Italian and Dutch samples, reflecting country-specific dynamics in organized crime involvement. Evidence suggests minimal generational shifts towards more serious offending, but notable impacts of social changes, especially in anti-drug and anti-organized crime policies, across individuals born in different decades. ConclusionsBoth the societal context (‘where we are’) and temporal influences (‘when we are’) are essential in understanding criminal careers. Changes in policies and social conditions differentially affected organized crime offenders in Italy and the Netherlands.