22 WTF Vince McMahon Moments

8. Winning The 1999 Royal Rumble

The 1999 Royal Rumble match was focused around McMahon's efforts to ensure that Stone Cold had "no chance in hell" of winning the Rumble for a third year in a row. He therefore placed Austin as the #1 entrant, offered a $100,000 bounty to whoever eliminated Austin, and entered himself into the Rumble as #30. However, Commissioner Shawn Michaels reversed this and made McMahon #2, leading to an unforgettable Rumble match which saw Vince and Austin battling all over the arena, as well as Austin being temporarily taken out of commission by the Corporation. Vince and Austin were the final two men, and after The Rock came down to the ring to distract Austin, Vince managed to eliminate him and win the Rumble. Again, this could've so easily been ego-maniacal nonsense, but it was terrific storytelling and a too-good-to-be-true moment.
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Stay at home dad who spends as much time teaching his kids the merits of Martin Scorsese as possible (against the missus' wishes). General video game, TV and film nut. Occasional sports fan. Full time loon.