Everyone saying Shogun and some saying its not close (that's crazy talk). So imma go with Wanderlei! He had the better career, he was pretty much the sole ruler of the middleweight division in his era, had an amazing win streak. The level competition gots to be pretty close, but I'm going with Wand. I feel like he had better wins, made more money, and was more popular. He fought to a draw with CroCop in a fight he clearly won, Moved up and fought a 300 pound Mark Hunt on short notice and should of got the W. Beat Hendo fairly one sided the first fight. Rampage 2x, Arona, Saku 3X, Jardine, Cung Le, Bisping, Brian Stann. They both fought anyone and everyone. My vote is Wanderlei SilllllVVAAAAAAAA