The bit that makes the hypothetical so silly is that GSN kicked off their $100k Pyramid just before a tournament period in which the eventual winner bogarted the winner's circle in much the same way as that butthead kid in kindergarten who would take all the good blocks, leaving nothing for you. She had been after the big prize seven times, shooing away those pesky interlopers, working on it until she won (and the pressure was off a little bit in the second half, because she was going to be back anyway.)
There's a stable of about twenty or so Pyramid regulars from that time that I would trust to help me get to the top of the Pyramid, so picking one is both (say it with me) silly and hypothetical. I'm not going to say "Der, William Shatner! Derp!", but I also think that I would have more than one chance at the money, because I'm decent at the main game.