The dumb thing about the night after wrestlemania is that the fans were clamoring for a Triple H vs Austin title feud.
Either Austin should've stunned Vince or Triple H should've made the save. Trying to make Undertaker the face of the company before the Invasion was a mistake.
Also you're right. Rock should've had a long reign after Backlash but they were so hellbent on getting a Triple H over, were him and Steph even dating in real life then.
If so, the answer to OP's question is Triple H and Stephanie on and offscreen killed the Attitude Era inadvertedly.
Yeah, Undertaker and Kane are not who you fukking build the company around. They were always popular but never centerpiece popular. All-Stars, but not franchise players, basically. And Benoit and Jericho were kept under the glass ceiling for so long that nobody bought into their pushes.
As great as 2000 was, all of the stuff that's been plagung the product for the last 15 years got their start that year. Particularly the second half of the year after King of the Ring.
One constant from 97-99 is that you saw the elite midcarders get elevated, even while the main eventers were doing their thing. In '97, it was all about Bret/HBK but then Austin got elevated to their level. In 98, while Austin/Undertaker/McMahon was the main thing going, Rock and Foley rose up too. And then in '99, HHH got the push and Rock reached a new level as an elite babyface too.
In 2000, that stopped. Yeah, Kurt Angle won the strap but he was treated like a complete joke, and then Benoit and Jericho just remained stangant in the mid-card. Like the other guy mentioned, even after Rock came out on top in KOTR 2000, HHH remained the centerpiece of the shows and that took the energy out of things.