Wittgenstein's philosophy is not beyond criticism, of course, but Grayling's critiques seem to grow out of a misunderstanding of that philosophy.
[P]hilosophy is in Wittgenstein's view a therapy; the point is to dissolve error, not to build explanatory systems. The style is accordingly tailored to the intention. It is vatic, oracular; it consists in short remarks intended to remedy, remind, disabuse. This gives the later writings a patchwork appearance. Often the connection between remarks are unclear. There is a superabundance of metaphor and parable; there are hints, rhetorical questions, pregnant hyphenations; there is a great deal of repetition....Wittgenstein's style is expressly designed to promote his therapeutic objective against the 'error' of theorizing (p. 132).As a description of Wittgenstein's conception of philosophy and his method of doing it, this isn't too off. But readers are, according to Grayling, best advised to ignore these aspects of Wittgenstein's thinking. His programmatic remarks about philosophy, his "own official avowals about therapy and the avoidance of theory" (p. 133) are deceptive. Wittgenstein denies that his writings contain systematically expressible theories, "[but] indeed they do" (p. viii). A careful examination of his scattered remarks will uncover a philosophical theory of meaning and language with "an identifiable structure and content, even if neither, in their turn are as transparently stated and as fully spelled out as they might be" (p. 133). This conclusion, however, is possible only by doing substantial violence to Wittgenstein's texts. But this is a consequence Grayling is ready to accept, as he finds no merit in Wittgenstein's writings as such: they fail in a major philosophical duty: "namely, to be clear" (p. 133). Wittgenstein's organization of his thoughts is obscuring rather than illuminating their philosophical content. Not only are his writings summarizable "but in positive need of summary" (p. viii).
There is one way of taking this as a charitable interpretation of Wittgenstein. When someone rambles, one should do one's best to make out what he is rambling about. From a different perspective, however, this is entirely misplaced charity. Taking Wittgenstein seriously as a philosopher, requires taking his writings and the conception of philosophy they express seriously too. Language sometimes confuses us. Often we react by searching for order in the complexity. But this is confused too. Order is not what we need (nor is it to be found). The solution is getting an overview. Hence, Wittgenstein's writings are designed to ease the grip this and other deep-rooted philosophical ideas have on our thinking about language and the world, not by replacing these ideas with new ones, but rather by making their status as metaphysical ideas perspicuous to us. If we think there must be something common to everything called "games", or else they would not all have the same name, Wittgenstein's suggestion is: Don't think, but look! (PI, 66) When philosophers use a word -- "knowledge", "being", "object", "I", "proposition", "name" -- and try to grasp the essence of the thing, he encourages us instead to ask if the word ever actually used in this way (PI, 116). When our thinking ties itself up in philosophical knots, what we need is not another theory, for theorizing is often what gets us into trouble in the first place, what we need are methods for untying these knots.
Hans Sluga (whose latest Wittgenstein book I also read this summer) agrees with many of Grayling's descriptions of Wittgenstein's writings. But he makes something entirely different of them:
Wittgenstein covers an exceptionally wide range of philosophcal and quasi-philosophical matters and ... he manages to speak about them with an unusual freshness, in a precise and stylish language, often with the help of surprising images and metaphors. This has suggested to ... a group of readers that what is of greatest interest in Wittgenstein's work is the manner in which he engages with philosophical questions. On this view, Wittgenstein teaches us above all some valuable methodological lessons (p. 16).At one point, Grayling calls this "a neat apology for obscurity". Further down the same page, however, he suggests:
Perhaps the value of Wittgenstein's work lies as much in its poetry, and therefore its suggestiveness, as in its substance. There is no doubt that in this respect Wittgenstein's work has stimulated insights and fresh perspectives, especially in philosophical psychology, which have helped to advance thought about these matters (p. 133).At first blush there seems to be a tension here. If Wittgenstein has helped advancing thought, he has done so by helping us see our thinking afresh. Descartes' cogito argument, for instance, troubled Western philosophers for centuries. How could we possibly break out of the prison of our own minds? The so called private language argument doesn't solve this problem, but if it convinces us that the question is confused, the argument might dissolve the problem for us. By curing us from confused thinking, a successful Wittgensteinian "therapy session", one might argue, results in the exact opposite of obscurity. But Grayling doesn't think so. On his view, philosophy (unlike therapy) is not simply combatting wrong perspectives on things, but also constructing explanatory thought-systems. And it is of course true that Wittgenstein's writings seem obscure when read as attempts to rise to these demands. However, as I have argued, I believe Grayling is wrong in assuming that Wittgenstein (contrary to everything he writes) is trying to answer to these demands.
Here I am not arguing that all philosophy should be conducted in the manner of Wittgenstein (in a sense that would be impossible: if we were never tempted to theorize, "therapeutic" philosophizing would be superfluous too). What I can offer, though, is an example of how such philosophizing might work. Grayling writes that...
... it is a mistake to suppose that reminding ourselves of the main uses of words like 'good' and 'true' is enough, by itself, to settle any questions we might have about the meaning of those terms. Indeed, it is notoriously the case that question about goodness and truth, which are paradigmatically large philosophical questions, cannot be resolved simply by noting the ways 'good' and 'true' are as a matter of fact used in common parlance -- that is, in the languagegames in which they typically occur. It would seem to be an implication of Wittgenstein's views that if we 'remind' ourselves of these uses, philosophical puzzlement about goodness and truth will vanish. This is far from being so (p. 115).When someone asks what "good" means, a Wittgensteinian would answer with a question: "What particular use of the word 'good' are you thinking about?" The meaning of "good" depends on whether you are thinking of a good taste, a good night's sleep, a good footballer, a good deed, or a good person. Forcing you to reflect harder on what you meant, this challenge might convince you that your initial question was confused. On the other hand, this needn't work, because you might, as Grayling suggests, just as well rephrase you question: "Not 'good' used in a particular way, but goodness as such." This, of course, is the kind of philosophical puzzlement Wittgenstein's "therapeutic method" is designed to combat. The fact that such reminders don't always work certainly is no proof that Wittgenstein's conception of philosophy and his manner of doing it is wrong. It only proves that his therapy doesn't always work. And there is no problem with that. Because Wittgenstein never said, as Grayling has him saying, that reminders about ordinary language use by themselves could make philosophical puzzlements go away. In addition one needs the will to receive these reminders in the right spirit. Philosophy, on Wittgenstein's account, is a fight against one's own temptation to view things in a certain way. It is not a given how that fight will end.