2007
Winner – The Undertaker
Who should have won – Shawn Michaels
Reason – If you knew that HBK was going to challenge John Cena for the WWE Championship at WrestleMania 23, and you knew that match was going on last, why would he not win the ultimate prize to get there first? Instead, they gave it to The Undertaker only for him to challenge for the lesser of the Two World Championships and then they put that match on 4th.. I simply don’t understand the booking there.