Federal criminal sentencing doctrine is growing increasingly favorable to the prosecution. This Note identifies two factors that contribute to this “doctrinal drift.” First, district courts rarely issue written opinions in the sentencing context. Second, prosecutors, unlike defense attorneys, can strategically forego appeal in an individual case to avoid the risk that the lower court’s pro-defense reasoning will be affirmed and become binding precedent. In fact, 99% of all appeals of sentencing decisions are defense appeals. When defendants appeal pro-prosecution lower court decisions, the appellate court usually affirms, in part due to deference. The result is a one-sided body of case law, composed primarily of circuit court opinions affirming pro-prosecution decisions. Consequently, when defense attorneys draft sentencing memoranda, they face a dearth of precedent to support their position. Prosecutors, by contrast, can choose from an abundance of favorable decisions. Consequently, prosecution memoranda are more likely to persuade the court, and with each round of appeals the doctrine drifts further in the pro-prosecution direction.