As a landmark philosopher of language and of mind, Ludwig Wittgenstein is also remarkable for having crossed, with apparent ease, the "continental divide" in philosophy. It is consequently not surprising that Wittgenstein's work, particularly in the "Philosophical Investigations," has been taken up by philosophers of education in English. Michael A. Peters, Christopher Winch, Paul Smeyers and Nicholas Burbules, and others have engaged extensively with the implications of the later Wittgenstein's philosophy for education. One challenge they face is Wittgenstein's use of the word "training." It appears throughout his discussions of language learning and in his periodic references to education. This is made all the more problematic by realizing that the German term Wittgenstein uses consistently is "Abrichtung," which refers to animal dressage or obedience training, which is currently used in sadomasochistic practice, and which also connotes also the breaking of an animal's will. I argue that this little-recognized fact has broad significance for many important Wittgenstinian insights into education. I conclude by considering how an unflinching recognition of the implications of Wittgenstein's word choice might cast him as a pessimistic or tragic philosopher of education and upbringing--following German-language traditions--rather than as thinker more compatible with progressive Anglo-American perspectives.