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This chapter analyzes pragmatics in relation to the concepts of transparency and context in legal communication. First, the basic argument offered in Marmor’s The Pragmatics of Legal Language is critiqued. Second, I use Dascal’s Transparency and Doubt: Understanding and interpretation in Pragmatics and in Law to both critique and extend the agenda of a pragmatics of law. Third, I introduce two recent US Supreme Court cases, Smith and Bailey to give an example of dispute over the meaning of the word “use” in American statutory law. Finally, the analysis will be completed though the investigation of a more pragmatic conception of pragmatics. The argument will have two parts. First, it is ultimately argued that Marmor’s claim that law, because it is largely a domain of strategic action, does not benefit from “supplemental” pragmatic analysis, ignores complexities in the legal realm as well as the resources offered within a pragmatic pragmatics for a much more substantial understanding of law and legal discourse. Second, I argue to the contrary that a broader and more contextualized conception of pragmatics as exemplified by Dascal in “Transparency and Doubt,” and supplemented by insights from Peirce and Dewey, offers important tools useful in analyzing the domain of law and legal discourse.