#1 Shawn Michaels
It's no locker room secret that Shawn Michaels back in the late 80s and early 90s was literally untouchable from a booking standpoint and a financial one. Vince loved Shawn, and Shawn loved the love. Vince literally put all his eggs in one basket with Shawn, backing him in every decision, most notably the Montreal Screw job.
However, Shawn constantly pushed his luck and knew he could do what he wanted. The one golden rule of professional wrestling has always been to NEVER break kayfabe, regardless of whether you're in front of twenty people or a three million-strong TV audience, always stay in character.
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Infamously known as the Madison Square Garden incident, Michaels, Hunter, Nash & Hall would break kayfabe and hug each other in front of a packed crowd. This moment was so significant as it showed the adoring wrestling public that wrestling truly isn't real. On the flipside, Titus O’Neil was handed a suspension after he playfully hugged Vince McMahon during Daniel Bryan’s retirement ceremony on Raw and has been effectively buried ever since.
For Nash & Hall the repercussions were irrelevant because they were already on their way out, but for Michaels & HHH they'd have to stay and face the consequences if any. But as we all know when you're the apple of the boss's eye, there is no such thing as consequences.
If he wanted to, Shawn could have called himself the boss at times, the way he saw himself as above his peers. You only have to read the various accounts from ex-wrestlers who have come out and talked about how Shawn constantly abused them backstage, without any official intervening. Shawn not only broke the rules, he made the damn rules.
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