hehe well Kimbo would have a few months to gameplan for the leg kicks. Barry is def gonna stand with him. Fact is, with Kimbos skillset or lack there of, there just arent really any "safe" fights for him in the HW division. It will either be against a techniqually better striker or a ground game guy. I much rather give him the strikers of course.
Tbh I'd rather give him a sh*t grappler (say Al-Turk) than a very technical striker like Barry.
Against the sh!t grappler he might stuff the TDs and survive on the ground if it goes there. If he gets beat it wouldn't be a big deal since we all know BJJ isnt his forte. But against the good striker, he'd get embarrassed at his own game. lol
Imo the best options style wise would be a one dimensional brawler (Drew McFedries, Houston, Meat Head) or an average-decent striker (McSweeney etc..)