#2. Vince McMahon and The Montreal Screwjob
Bret Hart spat on Vince McMahon's face after the main event of Survivor Series 1997 while the face of the company wrote "WCW" in the air to indicate his move. There's not much that we can say that already hasn't been said about The Montreal Screwjob, but the fallout from it was perhaps the best thing that could have happened to McMahon and WWE.
Bret Hart was leaving WWE after Vince McMahon couldn't honor his lucrative long-term contract. WCW, who was splashing big money on the biggest names was willing to pay Hart what he wanted, so McMahon allowed his biggest star at the time to leave.
The controversy of the finish and Vince McMahon's interview justifying it made him the biggest heel in all of wrestling, and it helped create the "Mr. McMahon" character. Had there been no Mr. McMahon character, 'Stone Cold' Steve Austin and The Rock would never have reached the heights that they did in the Attitude Era.
It remains one of the most controversial moments in WWE history, but the decision that Vince McMahon made ended up benefiting him in the long run.