#1 The Montreal Screwjob
If you're a wrestling fan and don't know what the Montreal screwjob is, then you've probably just started watching wrestling. The incident that took place at Survivor Series 1997 in Montreal is still debated and talked about to this day. It was a highly publicized incident, and many believe it was this moment that the Mr. McMahon character was born.
Vince was seen for the first time to be more than 'just the announcer,' as he called for the bell to allow Shawn Michaels to 'beat' Bret Hart for the WWF title. Bret had refused to drop the title, promising to hand the belt over the next night on RAW. The only problem being, Bret was not contractually obligated to be at RAW, as he had signed with WCW.
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Perhaps, fearing a repeat of a WWF belt being thrown in the garbage - as Madusa, formally Alundra Blayze did on Nitro when she went back to WCW - and giving WCW ammunition to make Bret's run successfully at a crucial time, Vince took no chances. It stunned and angered the parochial Hitman crowd, the WWF attempted to cover themselves on TV, saying Bret had tapped out, JR presented an interview with Vince, sporting a black eye thanks to Bret.
It was amazing to see, for around two-three months, air-time given to a wrestler who was no longer even with the company. Even to this day, the screwjob finish is used, particularly in Canada, and fans to this day in Bret's homeland ridicule Earl Hebner - the referee gave the unfortunate task of officiating the match - Vince and Shawn Michaels with chants of "you screwed Bret."
The significant aspect is, of course, that Vince realized how disliked he could be by the fans, at a time when the Federation was lacking main event heels, and lead to a huge feud with Stone Cold Steve Austin which reshaped the landscape of the Monday Night Wars.