The United States v. Booker (2005) decision rendered Federal Sentencing Guidelines advisory rather than mandatory. In the context of this decision, this study examines both the direct influence of aggregate-level political, community and administrative variables on sentencing outcomes, and the way that such characteristics might contextualize individual-level predictors. Using multi-level regression techniques, this study examines the role of aggregate level variables on sentence length decisions across four distinct time periods. Moreover, this article also examines whether aggregate-level variables condition the effects of race/ethnicity on sentencing outcomes. While the direct effects of aggregate-level variables on sentencing outcomes are generally limited to political climate effects, there is evidence that political climate and other aggregate-level measures contextualize individual-level race/ethnicity effects. Future research should seek to better understand the specific mechanisms behind these relationships.