In Davis' autobiography, he mentions trying to work with Jimi. I don't think it would have worked really, but who knows. Jimi was completely self taught, while Miles went to Juliard, I don't see how they would have communicated musically, literally. Like, if Miles tells Jimi to try a diminished chord here, or some modal scale there, Miles would have ended up doing a LOT of teaching along the way. And I say this as a guitarist of 30+ years who loves both of them.