Abstract: This essay examines two jurisprudential styles in Judge Posner’s statutory interpretation opinions. Both approaches invite judicial flexibility. The first, which reflects an earlier stage in Judge Posner’s career, justifies interpretive flexibility by defending a process of “imaginative reconstruction.” On that view, because a busy and error-prone Congress will not always capture its purposes in the words it chooses, the court should try to figure out what Congress would have wanted to accomplish in the circumstances before the court. The second, and more recent, framework is more openly pragmatic. On that view, Judge Posner justifies interpretive flexibility on the ground that judges properly “enrich positive law with the moral values and practical concerns of civilized society.” To simplify, the first approach treats interpretive flexibility as a better way of decoding Congress’s instructions; the second treats it as a proper exercise of judicial power. While reiterating a preference for textualism, the essay argues that, between the two approaches outlined by Judge Posner, his newer, more pragmatic justification gives a more accurate account of what is truly going on in the courts and is more sensitive to the underlying institutional considerations that necessarily inform rules of interpretation.