Lol, I'm loving these comments!
Serious answer, I think CM Punk would win. I suspect that the reason Askren did so poorly against Jake Paul is that he didn't take him seriously, and he just assumed that because he's a true MMA fighter he can beat any Youtuber.
CM Punk, on the other hand, was at least humble enough to recognize that he didn't know anything, and he tried to learn in preparation for his UFC matches. Obviously, he didn't do great, but as anybody who trains here know, fighting IRL is hard.
So, if given the choice between two guys in their late thirties and bodies broken by years of competition in unrelated sports, I'll take the guy who shows he wants to learn over the guy who thinks he already knows enough.