The Federal Sentencing Guidelines, developed by the United States Sentencing Commission in the 1980s, appear to exemplify the turn from individualization toward aggregated, rationalized risk management that ostensibly became hegemonic in the late 20th century. In this article, we challenge that presumption by building on Harcourt’s (2007) argument that penal actuarialism emerged as part of the individualization project rather than as a repudiation of it. We trace how ‘criminal history’ came to be the primary mode for capturing defendant characteristics in the Guidelines formula, and delineate how time became the unit of quantification to transform criminal history into ordinal measures of current culpability. We draw three lessons from this case study: about the durability of old practices and logics; about how the individual penal subject lives on in sentencing regimes like the federal Guidelines system; and about the metrics of time and history as ways of knowing the juridical subject.