While recent Supreme Court decisions in Booker and Blakely have shaken the foundations of the federal sentencing guidelines system, careful analysis of the guidelines remains important. This Essay contends the federal guidelines have failed due to structural flaws that cannot be mended without fundamental reform. The failures of the guidelines can be traced to the breakdown of the institutional balance the Sentencing Reform Act was supposed to create. Power has consolidated in the hands of prosecutors at the case level and an alliance of the Department of Justice with Congress at the policy level. The inordinately complex sentencing table has given Congress and the justice Department a vehicle for constant intervention into the process of making sentencing rules. Because of the lack of budgetary constraints, this intervention has caused a one-way upward ratchet, in which sentences are raised easily and often and lowered only rarely and with difficulty. Likewise, the complexity and rigidity of the guidelines have severely constrained judicial sentencing discretion while conferring on prosecutors a vastly increased ability to influence a defendant's sentence. At the case level, there is an increasing disconnect between the sentences the rules ostensibly require and the sentences actually imposed as the front-line sentencing actors employ ever more mechanisms for evading the rules. All these problems are integral to the existing guidelines system and would not be materially alleviated by a post-Booker system of "advisory" guidelines.