#6 The Montreal Screwjob
Next on our chronological countdown is the most infamous moment in kayfabe breaking wrestling history. Back in 1997, the WWF had its back against the wall. Ted Turner's WCW promotion had lured away many of WWE's top stars with more money, a less exhausting road schedule and creative control.
In order to ensure that the top star of the era, Bret "The Hitman" Hart, would remain with WWE, Vince McMahon offered him a twenty million dollar twenty-year contract. In the contract, Hart would wrestle for roughly five more years before retiring to become a trainer and backstage official.
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However, McMahon soon realized he could not afford the lucrative contract. He persuaded Bret to break the contract voluntarily and even suggested the Hitman call WCW and see if they wanted his services.
Bret Hart did just that. It so happened that WCW was going to be legally allowed to announce Bret Hart's signing on air on November 10's edition of Monday Nitro. The only problem was, Bret was still the WWF World Champion.
Hart refused to do the job to HBK at Survivor Series on November the 9th, saying he did not want to lose in his home country of Canada. What followed was Vince McMahon conspiring with referee Earl Hebner to take the belt off of Bret without his knowledge. The Montreal Screwjob effectively smashed kayfabe into pieces and changed McMahon from a simple announcer to the vilest heel villain mastermind in wrestling history.