9. Shawn Michaels
The Heartbreak Kid Shawn Michaels has been under WWE contract for more than two decades now. He's been resigned twice in that time, yet on both events Vince McMahon has held him on an agreement. Why? Essentially out of admiration and appreciation for Shawn.
The primary occasion of this return in 1998 when Shawn went out with a back damage. He was away for a long time and was resolved that he'd never return, yet Vince continued sending a pay check. That comes from Vince and Shawn's quite undeniable fellowship. Without a doubt, the WWF would utilize Shawn in character parts on a couple events, yet basically Vince was paying Shawn to sit at home.
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