In this paper I discuss one facet of the multifaceted question of whether strong protection for intellectual property rights—in particular, rights in expressive works and in information in digital form—is, in principle, at odds with the First Amendment guarantee of freedom of speech. The question has assumed particular urgency in recent years because the Internet and digital technology seem to have rendered formerly serviceable legal boundaries obsolete, and doctrines that sufficed in a print-on-paper world no longer seem adequate. Vigorous debate rages about what has come to be referred to as ‘propertization’. Commentators ask whether, and how, and based upon what empirical assumptions, old boundaries ought to be redrawn and doctrines modified. The academic literature tilts heavily away from endorsing strong property rights in digitized content, and toward expanded user rights and intensified First Amendment review in copyright cases. This paper tilts in a different direction. It swims against the academic tide not only in the direction of its analysis but, more importantly, in the kinds of questions it considers relevant and in its analytical focus. Readers should understand that the analysis is deliberately provisional and suggestive rather than completely developed, and the conclusions are tentative. The paper does not purport to be a definitive study that draws confident conclusions. It is offered as speculation and in the hope that readers will approach it in that spirit.