The influence of Wittgenstein on Wallace has become a truism in the scholarship. This chapter explores the contribution of the philosopher and logician to Wallace’s fiction writing, focusing on the logical questions that are most directly present in the fiction. More particularly, the chapter offers a provocative look at Wallace’s philosophical entanglement with Richard Taylor and ideas of fatalism. Imagining an alternate world in which Wallace was a philosopher by profession instead of an author, the chapter traces the development of his argument against Taylor’s proposition by way of logic, one of the key philosophical features of his writing, and traces a path from here to the interest in Wittgenstein and language games that dominated his fiction. In imagining this alternative world, the chapter invites the reader to think through exactly the ideas of choice, contingency, language and logic that animate argument it discusses.