You probably will be able to get imitation in the not too distant future. But a world where we just listen to imitations of 50s and 60s derivatives of bebop is a sad one. The most loved musicians are ones who are pushing things forward and don't just imitate Trane endlessly or whatever.

AI would need to be able to do something like create The Bad Plus in 1995. That's an even bigger mountain to climb.

I have think you have defined the terms of battle. An improvisational jazz solo from a master vs one that is AI generated. I don't know this but I suspect that Monk had no idea where his solos were going when he started to play them. I like where they went, I'm just saying there were no directions.