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Wandy I think....
During 2006-2009 it was pretty widely accepted Shogun was the better fighter and the fact that he trained with Wand and was sort of his prodigy was the only reason he was held back from the Pride middleweight belt.
They had pretty comparable styles revolving around high intensity Muay Thai and defensive Jiu-Jitsu, tho I think Shogun had the better chin, harder punches and was better at head movement, wand tended to berserk forward with his head up where as Rua tended to bob and leap forward with a hook and finish his combos with leg/body kicks.
If you look at common opponents. Wand beat Rampage twice and lost once, both wins were competitive before his brutal finishes at an average time of about 8-9 minutes, Rua Annihilated Rampage in 4 minutes : Wand had 2 close decisions with Arona, losing one and winning a split one, Rua annihilated Arona in about 3 minutes, : Wand was knocked out by Henderson in there fight, Rua lost to Hendo twice in 2 intense wars : Both beat Nakamura convincingly, tho Wand finished him : Both beat the shit out of Kenahra
Looking at there record I'm amazed Wanderlei never fought Overeem, and I'm surprised Shogun never fought Belfort or Franklin
In my opinion peak vs peak, Shogun takes it. Although peak Shogun probably wins against any LHW fighter not named Jon Jones.
Everyone will say Shogun but imo, Wand would've big-brothered the fuck out of him.
I've got Shogun. Bigger, more agile, better takedowns and grappling. Wand could knock him out though. Would be one hell of a fight especially if it were in Pride.