I think comparing CJ to the shell of what was once John Wall is a bit disingenuous or maybe just hyperbolic but either way. CJ isn't broken, he is a legit scorer and can be a great passer. We don't know how good he'd be a defending with good back court defenders and playing primarily against ones. I think that Wall is probably overpaid by 25-26M and CJ is probably overpaid by 6-8M.
As far as getting someone on Holiday's level, that's what we're talking about with Simmons... at the very least. So you give up CJ and the type of draft asset package that the Bucks did to get Simmons if you have to. I just think Olshey is too "nuts" to do what is necessary.