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Researchers have considered criminal records as a major determinant of the sentence. Most existing research controlled for criminal records using the number of prior convictions and arrests, and did not take the nature of past criminal events into consideration. Theories of sentencing suggest the courtroom workgroup assess risk of the defendant and make decisions, which is inadequately modeled if only the number of prior criminal events are considered. This paper investigates the relationship between the trend of the severity of prior crimes and outcomes of cases in the criminal justice system. It seeks to introduce the criminal careers perspective into sentencing research, and contribute to the discussion on the use of criminal records in sentencing models. The paper uses the case processing information of a sample of defendants in New York State, and models their complete in-state criminal careers in the official records. It focuses on investigating the relationship between escalation—the change of severity of crimes—and the case outcomes.