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#5 The Infamous Montreal Screwjob
A controversial moment that brought a career-defining shift in Vince McMahon's role in the business was the Montreal Screw Job.
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A moment where the Boss intentionally manipulated the outcome of the bout, and changed it in order to let HBK walk out of Canada as the WWF Champion.
Since Bret Hart was already transitioning to WCW back then, the Hitman refused to drop the title in his hometown to HBK which led to Mr. McMahon to plan a shocking finish to the night.
While WWE acknowledges the moment now, the ending possibly propelled Vince McMahon to unimaginable heights, as he went on to become one of the greatest heels in the business, and was hated in abundance.
A moment of such magnitude might never be replicated again and will forever remain the most popular and shocking moments in the company's history that Mr. McMahon can never erase.
