There is widespread agreement in criminology that some crimes are more severe than others, but precise definitions of crime severity and straightforward methods for measuring it have been elusive. Public perceptions of crime severity and economic estimates of crime costs to society or willingness to pay offer a variety of metrics for the public's perceptions of severity, but they may not accurately describe severity as reflected in offender preferences. The behavior of offenders is critical for understanding developmental progressions in criminal careers, as one may assume that typically more severe offenses are not undertaken until less severe crimes have been committed. In the present paper we propose an alternative metric of crime severity, drawing on findings from developmental criminology that indicate that more severe crimes occur after less severe crimes in the criminal life course, and a method for estimating crime severity that uses the generalized Bradley–Terry model of multiple paired comparisons. We demonstrate this approach on two samples of youthful offenders: the National Youth Survey and the RAND Adolescent Outcomes Project. The results suggest that sample-specific estimates of crime severity can be derived, that these estimates provide insight into the developmental progression of crime, and that they correspond well to crime severity rankings produced by the public.