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This article offers a new critique of Federal Rule of Evidence 609, which permits impeachment of criminal defendants by means of their prior criminal convictions. The article draws on three aspects of the contemporary criminal justice system to show that in admitting convictions for impeachment courts are wrongly assuming that they are necessarily reliable indicators of relative culpability. First, courts assume that convictions are the product of a fair fight, despite the adversarial collapse revealed by the nature of plea-bargaining, the crisis in public defense, and the data on wrongful convictions; second, courts assume that convictions demonstrate relative culpability, despite the racial and other disparities that pervade law enforcement; third, courts assume that convictions connote moral culpability, despite the growth in prosecutions that require no culpable mental state. This article proposes that before a conviction is used for impeachment, there should be an assessment of the extent to which it is a reliable indicator of relative culpability. In support of its proposals, this article draws two new sources into the impeachment context. First, in a groundbreaking sentencing opinion, Judge Nancy Gertner refused to give the prescribed weight to the defendant’s prior convictions, since she feared that they were the product of racial profiling and that she would be compounding disparities. Second, the prosecution’s ethical duty to 'do justice' militates in favor of a prosecutorial assessment of a conviction’s reliability before proffering it for impeachment. Through these kinds of judicial and prosecutorial inquiry, the law of impeachment will hew more closely to the realities of the criminal justice system, and to justice itself.