Monroe Freedman was a severe critic of “philosophizing” about legal ethics, yet he was one of the most influential theorists in the development of theoretical legal ethics as an academic discipline in the late twentieth century. No philosopher can ignore Monroe’s arguments, many of which are as vital today as when he first articulated them. It is not just the arguments themselves that remain influential, however, but also a style of reasoning that is characteristic of legal argument at its best. Philosophers not steeped in the ethical world of practicing lawyers have a tendency to assume away many of the hard problems. For example, a dilemma may be presented on the assumption that a lawyer “knows” some fact—that the client is lying and will lie on the stand, that the adversary’s inexperienced lawyer has made a mistake, that a defendant was wrongfully convicted, and so on. One of the great virtues of Monroe’s work is its lawyer-like insistence on the centrality of facts and the difficulty of knowing what they actually are. It is easy to say that a lawyer should provide competent assistance and should keep a client’s confidences, but also a lawyer should not assist in presenting perjured testimony. Using one of his vivid examples, however, Monroe reminded us that a lawyer will not know the facts needed to provide competent representation without first giving the client an ironclad guarantee of confidentiality, which limits the lawyer’s options in responding to the client’s subsequent decision to testify falsely.