There is something to be said for preserving the past. It is important, but not necessarily at the expense of forging ahead as well. Why can't both exist? Our group does both old standards and new stuff.
As for the amp thing...does Wynton play with no sound reinforcement whatsoever? Every venue, every occasion? Does he use a mic when he preaches - I mean speaks - to audiences and workshops?
Sometimes I wonder if he's hurting jazz more than helping.
Just do a google search for pics of him... you'll find him playing into mics quite easily.
