1. Triple H
He was loved and popular as the leader of DX, but he turned against DX and changed his attitude. This was a new, more sadistic Triple H. He took out many superstars with his anger and an assortment of weapons, especially that sledgehammer.
2. Vince McMahon
Vince was still the bad guy in the Steve Austin feud. And just when he appeared to have a change of heart, he turned against the fans. He was hated until Triple H came along and became even more hated than him.
3-tie. Ernest Miller
The Cat annoyed millions of fans with his egotistical attitude and constant dancing.
3-tie. Big Bossman
Everyone hated the Bossman. He made everyone mad in 1999. First he killed Al Snows dog, leading up to a long, boring feud between the two. When that ended, Big Bossman exploited the cancer of Big Shows dad. His attacks were ruthless and sick and upset everyone.