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Undertaker already beat Triple H at Wrestlemania XVII, and it was actually a really good match. I think Undertaker even offered Triple H the opportunity to end his undefeated streak, but Triple H refused. Shawn Michaels always puts on a good show, but there's one person that you're forgetting that Undertaker still hasn't faced at Wrestlemania, and that could be a possible opponent for next year, if Undertaker still hasn't retired by then; Chris Jericho. The guy is just as good, if not better, than Shawn Michaels.
That battle was around 8 years ago, and that was when HHH was quite convincing. Compare to HHH nowadays, who's winning championships because he's the son-in-law of Vince, and has waived credibility. I can't say HHH is a bad wrestler, but he has decayed from his moment at Evolution. Plus, he's not a good face; he's better as a heel.
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They've given Randy Orton more than five years to "polish his skills," and even though he's now a main-eventer, that doesn't disregard the fact that he absolutely sucks. It just goes to show that you don't have to be a good wrestler to make it in the business. Just look at guys like Hulk Hogan or the Ultimate Warrior. They sucked, and yet, they headlined Wrestlemania VI together. Go figure.
Bolded your statement just because you don't have to quote Hogan or Warrior for that. John Dinner is doing the same thing, over, and over, and over again. But that doesn't take the point that DiBiase Jr. isn't ready to make that step. Though, if his mic skills improve by the year, he'll be set for a championship instead of being Taker's last match.