Much of the best contemporary work in the philosophy of language and content makes appeal to the theories developed in generative syntax. In particular, there is a presumption that—at some level and in some way—the structures provided by syntactic theory mesh with or support our conception of content/linguistic meaning as grounded in our first-person understanding of our communicative speech acts. This paper will suggest that there is no such tight fit. Its claim will be that, if recent generative theories are on the right lines, syntactic structure provides both too much and too little to serve as the structural partner for content, at least as that notion is generally understood in philosophy. The paper will substantiate these claims by an assessment of the recent work of King, Stanley, and others.