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. In admitting convictions as impeachment evidence, courts are wrongly assuming that such convictions are necessarily reliable indicators of relative culpability. Courts assume that convictions are the product of a fair fight, that they demonstrate relative culpability, and that they connote moral culpability. But current prosecutorial practice and other data undermine each of these assumptions. Accordingly, 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, because 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 the prosecution proffers it for impeachment. Through these kinds of judicial and prosecutorial inquiries, the law of impeachment will hew more closely to the realities of the criminal justice system, and to justice itself.