Wittgenstein wrote nothing on legal theory or law, so there is no obvious textual basis on which to draw possible connections between Wittgenstein and legal theory. And Wittgenstein abhorred theorizing in philosophy. So the odds are slim that Wittgenstein would have accommodated himself or his work to similar activity in the law. Where does this leave us?
At sea, which is where we normally are in life and, thus, where Wittgenstein wants us to recognize ourselves as being when doing philosophy too. But theory can disguise this fact from us, as it also can make us think that we have unrivalled powers of knowledge and understanding and explanation. Wittgenstein's criticism of theory, or the activity of theorizing, is meant to get us to see, and to acknowledge, our limits in this respect. But even though his terms and intent are mostly negative in tone and thrust, his criticism of theorizing has positive implications for how we should try to understand what we are doing and what we have done, including what we are doing and have done in the law. So, if understanding the law better is something that legal theory does or tries to do, and Wittgenstein's later work can help us understand the law better, then Wittgenstein's later philosophy is connected to the task set legal theory.
Eisele, Thomas D., ""Our Real Need": Not Explanation, But Education" (1990). Faculty Articles and Other Publications. 31.