Shawn Michaels has been on the WWE payroll longer than any other performer on this list. Even now, with HBK technically retired, Vince McMahon still has him under employment as a WWE ambassador. Even when Michaels went out with an injured back in 1998, for four years McMahon kept paying him. Why does the chairman hold Michaels in such high regard? Perhaps it was the fact he was the greatest in-ring worker ever to wrestle on WWF shows, more likely it was the fact that HBK sought McMahon out and made the effort to create a personal friendship. This led to an understanding and creatively inspirational relationship which aided the WWF immensely - many of Michaels suggestions went on to inspire the Attitude Era design. D Generation X wasn't a Vince McMahon creation, it was a Shawn Michaels creation. The ultimate showing of the star's loyalty came at Survivor Series 1997 when he willingly 'screwed' Bret Hart for McMahon. That proved when it came down to it, Michaels would always side with Vince over the boys in the locker room. His loyalty is purely WWF and he was also the biggest WWF name of the Monday Night Wars not to abandon ship to WCW (albeit he did make some noises about it). Nash, Hall, Hart, they all went, but Shawn Michaels remained true to Vince McMahon.
