Many tobacco company trademarks, such as MARLBORO, are extremely valuable. But valuable trademarks are often vulnerable both to copyists and to parodists. Tobacco trademarks face the additional vulnerability of onerous public health regulations, which can limit their appearance and use. When tobacco companies challenge these health regulations they do so on the grounds that the regulations violate their First Amendment speech rights. The law that is applied in these challenges is well developed, clear and predictable. When tobacco companies challenge unauthorized third-party uses of their marks, the speech rights involved are dealt with in a distinctly different manner. Under trademark law there is an assortment of approaches to protecting speech therefore making it difficult to predict outcomes. How can the non-false use of a trademark be so robustly protected as speech in one case and so slackly protected in the other? Juxtaposing these areas of law through the litigation strategies of one industry reveals curious presuppositions about speech in both laws.