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Throughout the life course, life events can affect the way individuals lead their lives. This may even be more true for criminals. These life course events can affect: a) if and when an individual begins a delinquent or criminal career; and b) whether or not the offender continues to engage in criminal behavior or desists from further criminal activity. Thus, delinquent and criminal careers are dynamic – they start, continue and even escalate, or just end. Juvenile delinquents do not necessarily proceed to become adult criminals. And, adult criminals do not necessarily begin their careers as juvenile delinquents. Thus, this study seeks to answer the following questions about juvenile chronic offenders and their trajectory into adulthood: Are there pro-social factors that lead to desistance from a chronic criminal career? Are there negative life transitions, which foster the continuation of a criminal career first begun as a juvenile? Using data from the 1958 Philadelphia Birth Cohort, we investigate five life transition measures: financial, familial, peers, victimization, and court dispositions. These measures were tested because they offer insight into the transitions over the life course that can affect whether or not an individual desists, persists, or begins a criminal career.