2. The Montreal Screwjob

After two decades, the Montreal Screwjob remains an intensely controversial development in wrestling history. With Bret Hart on his way to WCW, the WWE Champion was unwilling to drop to the title to Shawn Michaels. What was Vince McMahon to do?
The choice to “do business for” was morally dubious at best. Michaels had betrayed Hart's trust and doing the job in his home country could tarnish 'The Hitman's' legacy. Nonetheless, in the heat of the Monday Night War, it is also understandable why McMahon would feel compelled to take extreme measures to protect his top championship and his company.
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Maybe McMahon could have done business more nicely. The choice he did make kept the title safely in WWE’s possession. Moreover, The Screwjob generated buzz that led to the creation of the Mr. McMahon heel character, not to mention setting up The Rock’s iconic turn at Survivor Series one year later.