This article examines the 2011 Supreme Court decision in United States v. Freeman. At issue was whether defendants, such as Freeman, who enter a guilty plea pursuant to a binding plea agreement, are entitled to seek a modification of their sentence when the guideline range applicable to their offense has subsequently been lowered by the United States Sentencing Commission. By a five-to-four vote, the Court found that Freeman was eligible to seek a sentence reduction. However, as the article explains, the concurring and controlling opinion of Justice Sotomayor may ultimately prove to be problematic for criminal defendants generally and for the Commission for many years to come. In her opinion, Sotomayor suggests, in dicta, that the government can preempt future sentencing reduction claims through the insertion in plea agreements of waiver clauses. Should the Department of Justice adopt such a policy, the article warns of (and describes) the long-term adverse consequences that such a decision would have for criminal defendants and for ability of the Commission to achieve equity through guideline sentencing. As part of its critique of Freeman, the article also explains why the Freeman Court erred in its analytical approach. In so doing, it illuminates the real world of plea bargaining in the Freeman context, and explains why this plea negotiation truism provides a sounder, firmer, and clearer foundation to decide not only Freeman-type cases but any such case involving a sentence reduction claim. The article also uses Freeman to highlight and correct a common misunderstanding about the nature of plea agreement contracts. It explains why plea agreements have been erroneously construed as unilateral arrangements between the prosecution and the defendant, and why they should properly be interpreted as bilateral contracts involving three parties — the prosecution, the defendant and the court.