WWE: 10 Greatest Moments Of Austin Vs McMahon Feud

9. St. Valentine's Day Massacre

On Valentine's Day 1999, the WWF put on a pay-per-view called St Valentine's Day Massacre. The show would be headlined by a Steel Cage Match between Austin and McMahon, with McMahon's WWF Title shot at WrestleMania on the line. Heading into the event, I remember wondering just how the match was going to go. Vince has always been in great shape, but come on... he was in a Steel Cage with his most-hated rival, who, on top of having a chance to beat the life out of him, could also win a main event spot at WrestleMania in the process? It wasn't a matter of if Austin would win. It was more of whether or not McMahon could make it last more than five minutes. As is the case with every match Vince has ever participated in, this was more entertaining than it had any right being. Everyone got a sick joy out of watching Austin destroy McMahon, get ready to leave the cage, go back in, destroy McMahon some more, get ready to leave the cage, go back in, and so on. When it looked like things were about ready to end for ol' Vince, we got the WWF debut of Big Show, then going by his real name, Paul Wight, fresh off of a very successful run as The Giant in WCW. Wight popped up through the canvas and went after Austin right away, tossing him into the side of the cage time and time again. Finally, he threw Austin into the cage with such force that the panel popped open completely, and Austin fell to the ground as the winner, while a dumbfounded Vince looked on. It wasn't exactly a five-star classic, but it did what it was supposed to do. It provided an entertaining beating, got Austin to the main event of WrestleMania 15, saw the debut of a new main event player, and had Vince wanting revenge yet again.