10 Times WWE Royal Rumble Winners Risked It All Before WrestleMania
1. Vince McMahon - 1999
It should've been three Royal Rumble wins in a row for 'Stone Cold' Steve Austin, but instead we got the absolute worst winner in Rumble history...
The Austin-McMahon rivalry was the talk of the industry in 1999, so having the two of them be the first participants in the Royal Rumble match made sense. Vinny Mac was so determined not to let Stone Cold win that he issued a $100,000 bounty for the man who eliminated his nemesis. McMahon had even tried giving himself entry number 30, but Commissioner Shawn Michaels had bumped him all the way down to two instead.
With the enemies fighting all around the arena, they were eventually the final two entrants. Thanks to a distraction from The Rock, the Chairman threw Austin 3:16 over the top rope and won the Rumble. Why was this allowed to happen? The biggest star in the industry, on his way to winning a record-breaking third match in a row, beaten by a former commentator and businessman... welcome to 1999.
Everybody knows that we got The Rock vs. Steve Austin at WrestleMania XV; the journey was even more convoluted though. McMahon decided to give up his match, until contract expert HBK came to the rescue again, informing the Chairman that the runner-up would take his place instead. A match was set for St. Valentine's Day Massacre: In Your House inside a steel cage.
After some shenanigans, the two finally entered the cage and the bout was on. Enter, Paul Wight. The future Big Show ripped a hole in the ring and came to Vince's aid, right up until he threw Austin straight through the cage and out onto the floor. It was over and Stone Cold was on his way to WrestleMania again.
The swerve for the sake of it, giving a non-wrestler one of the biggest wins of the year, was not worth the tedious journey. Austin was robbed of his title match in 1997, so got some revenge here, going on to beat The Rock and raise the gold at the Granddaddy of Them All once again.
Interestingly, this was also the final In Your House event to take place.