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GSP > khabib in the striking, GSP can win just by defending the takedowns, he won't really hurt Khabib, just outpoint him with longer reach jabs and low kicks.Does khabib have the power to push gsp back though? (With his hands) Will be very interesting if GSP takes his best and pushes forward
GSP can most likely take khabib down too, but I doubt he can do much on the ground, other than maybe lay in khabib's guard. If I was him, I won't try a heavy wrestling gameplan on Khabib, he ll gass and get slower, Khabib is already arguably one of the fastest LW on earth, if GSP get too slow, he won't be a danger anymore.
Now what it is really interesting is what happen if Khabib takes GSP down. I think it depends where it happens, in the middle of the cage, GSP might just explode and get back up, but against the cage I think he is in a very bad spot. Cage wrestling showed to be GSP only " weackness " in his GOAT tier MMA grappling.