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Fred CAt $269 a pop I would think he could look up and smile. Heck, if I were charging $269 for a signature I'd be looking up at the person smiling and wonder why the heck would you pay $269 for my signature.
He'd bring in over a quarter million dollars with less than 1,000 signatures. Of course the promoter gets the big cut but I'm sure Willie said, "Say hey, I want a HUGE slice of that action, partner".
I got my Willie signatures in the 70s and they were free back then.