Ludwig Wittgenstein was a reclusive and enigmatic philosopher, writing his most significant work off campus in remote locations. He also held a chair in the Philosophy Department at Cambridge, and is one of the university's most recognized even if, as Ray Monk says (1990, 401), 'reluctant professors' of philosophy. Paradoxically, although Wittgenstein often showed contempt for the atmosphere at Cambridge and for academic philosophy in particular, it is hard to conceive of him making his significant contributions without considerable support from his academic colleagues, his research fellowship and later teaching career at Cambridge. It is this conflicted relationship we explore, between the revolutionary thinker and his base within an educational institution. Starting from a brief biographical sketch of Wittgenstein's academic life at Cambridge, including his involvement as a student and faculty member in the Moral Sciences Club, we look at how he reconceived the role of philosophy throughout this period of creative antagonism. Throughout his work, from the early "Tractatus" to his 'Lecture of Ethics', and again later in his "Philosophical Investigations," Wittgenstein drew a boundary between empirical science and philosophy: the latter defined as an investigation of language and the limits of meaning. Seldom at home at the university, he was also at odds with his chosen field, offering a therapeutic approach that allows readers 'to stop doing philosophy when they want to' (PI §132). We conclude our investigation of Wittgenstein's relationship with the university and academic philosophy with insights from Pierre Hadot on philosophical inquiry as a vital part of the "bios," a "form of life" that is the life-blood of academia. Hadot offers insights on Wittgenstein's self-limiting narratives as a crucial aspect of what makes universities such important and enduring institutions, in spite of the vitriolic criticism they draw from iconic members like Wittgenstein.