Well IceSpear and MTTreasurer ability to accurately forecast elections is quite stunning. For instance, they were one of the few people to call NV-SEN properly.
idk, IceSpear whiffed big time on KY-GOV (although, to his credit, he was happy to eat crow for that).
Santander seems to have led a pretty eventful life, although it's hard to tell how much of it is kayfabe. Afleitch is also a good answer due to his long and difficult-to-predict political and religious journeys. TJ is fairly reticent about his personal life these days but he's moved around a lot.
IceSpear did kinda vanish though after that race.