#9 Don’t Like Benoit: Triple H
While Triple H got his start on the national wrestling scene as an up and coming heel for WCW, make no mistake about his allegiances. He turned down a big money offer to re-sign with WCW in favor of getting more opportunities to hone his craft, and more room to grow as a star under the WWE banner. It would turn out that he picked the right side, as Helmsley not only became a top shelf star with WWE, but WWE would end up winning out in its competition with WCW, ultimately buying out its rival.
Chris Benoit came to WWE before WCW went out of business. According to Chris Jericho, Helmsley's reaction to Benoit was that he was “OK” as an in-ring talent. Jericho immediately dismissed the comment as biased against anyone from WCW and protective of his spot. Regardless, the read on Benoit bespeaks The Game’s disdain for him. We can only assume that he resents Benoit all the more for the way his life would ultimately go.
The Benoit family tragedy was a black eye for WWE as a company. On top of that, it all but erases some of Helmsley's best performances opposite Benoit—particularly at WrestleMania 20—for WWE’s refusal to acknowledge them now.