When you get the nickname "The Cerebral Assassin" it's because you're considered a smart guy. He's also pretty smart because he realized the "Greenwich snob" gimmick really wasn't going to get him far and he had to be a more normal guy, so that led to DX Triple H and the rest is history. The gimmick really isn't that of an intellectual on the surface, but in the way he was booked throughout the years he certainly portrayed the role of an intelligent wrestlers. It's not like he was out there playing a dummy. Now that he's Chief Operating Officer Triple H he's in another role where he is portrayed as a smart guy who has everything going for him in life. It's a natural heel gimmick that he's yet to embrace although when he does he'll get a lot of heat for it. If you question why he's #1 on the list, just think about this: He dumped Chyna and married the boss' daughter Stephanie McMahon. That's the smartest move that anybody could make.