This study analyzes what accounts for offending careers from adolescence to young adulthood. The research takes advantage of a longitudinal data base collected from a sample of approximately 500 adolescent males who were initially interviewed in 1982-83 when their ages ranged from 11 to 17 and reinterviewed in 1990-91 when they were ages 19 to 25. Sampling for the study was carried out in two stages: First, 12 urban neighborhoods representing a crossed array in terms of levels of family disorganization, neighborhood, social rank, and predominant race group (black or white) were selected. In the second stage, households in each of the areas were listed and screened. Eligible households were then grouped into single vs. two-parent households and stratified random samples were drawn. The purpose of this study is to (1) identify contextual and individual-level risk factors associated with patterns of onset and suspension of offending; (2) delineate the relationship among type of community context, characteristics of interpersonal networks, and offending behavior in young adulthood; and (3) develop a model of change and stability in offending which incorporates individual level risk factors and the conditional effects of social context. Substantively, the research builds on extant longitudinal studies in postulating the effects of early behavior and of later role transitions on the dynamics of change over time. Distinctively, it also examines the conditional effects of macrosocial factors on these individual-level processes. The importance of cross-level theorizing and related empirical study cannot be overemphasized. Linking neighborhood characteristics and individual factors is a long overdue research strategy in this arena of work. By focusing specifically on these macro-micro linkages, this study promises to advance our most basic understandings about delinquency and crime.