This essay considers the possibility that computers might soon be capable of writing many of the documents lawyers typically write, and considers what qualities of writing are uniquely human and whether those qualities are sufficient to render human written work superior to computer generated work. After noting that despite the claims of rhetoricians and narrative theorists, not all legal writing is persuasive writing, and that it is in the non-persuasive area of prosaic, functional documents that computer generated documents might gain a bridgehead into the legal market, the essay tracks the development of computer-generated written work, particularly in the areas of sports journalism and corporate reporting. The essay notes that the templates developed to generate these documents can be customized to produce the tone desired by the customer, meaning that both rhetoric and narrative have been captured and transformed into tools that can be manipulated by computer programmers. This in turn means that computer generated documents will not be devoid of rhetorical or narrative interest, making the programs that develop them potentially appealing for lawyers even if they seek to use them to draft persuasive as well as more functional documents. What these programs will lack, however, is empathy -- the ability to anticipate what information a reader will need from a document, and when the reader will need it, and to draft a document that meets the reader's needs and expectations. An empathetic human writer knows when to follow and when to break the genre expectations of a document and can send powerfully persuasive messages to a reader by use of that knowledge. The essay concludes that empathy is a crucial, and uniquely human, aspect of persuasive writing and that an empathetically-aware written document should be superior to a technically accurate but non-empathetic computer generated document.