I think Miles was a great businessman, and had quite a hand (as did Columbia) in pushing his music. Less so Trane, but still...
There are those artists who create work that is on the surface rather uncommercial, but through either their own ability to hype or the record company's, get a lot of notice. Or perhaps they've got just enough balance between "out" and "in" to be magically appealing to both interests (Sonic Youth being a good example - hella businesspeople as well, natch).
Jimmy Guiffre made some weird-ass music; love it, but can't imagine it being for "everybody."