The Undertaker hasn't got the longevity to turn heel, nor would anyone really want to boo him, in my view. I doubt the Undertaker makes it to WrestleMania 30, and he'll only have two matches at best - one at WM 28, one at WM 29. This just doesn't give him any real time to become a believable heel, or to recover from it. Suppose he comes back after the Elimination Chamber PPV this year. How can he really become a believable heel in a few short weeks? I mean, sure, he could show up and attack Punk or a hypothetical face Jericho or something like that, but would you really but it? With only a few weeks to turn heel and build a feud, when for years the Undertaker has been billed as a transcendent figure whose heel/face alignment is superseded by his legendary aura, I just don't believe that he can really become a proper heel. If he had months to do it, maybe. However, even under those circumstances, I still don't know that it's a good idea.
For one, how many people really want to boo the Undertaker at this point? He's been overwhelmingly cheered for years now. I just can't really see the crowd turning on him no matter what he does. Furthermore, considering it won't be long before he bows out and finds himself in the Hall of Fame, I don't see the sense of this idea when he'll want to enter the Hall with all of his current prestige intact. Ultimately, I just don't feel this would be a wise decision at all, not with all the constraints surrounding it. Best to keep the Undertaker as is and continue booking him in big time WrestleMania matches for the next year or two before he finally decides to hang it up.
For one, how many people really want to boo the Undertaker at this point? He's been overwhelmingly cheered for years now. I just can't really see the crowd turning on him no matter what he does. Furthermore, considering it won't be long before he bows out and finds himself in the Hall of Fame, I don't see the sense of this idea when he'll want to enter the Hall with all of his current prestige intact. Ultimately, I just don't feel this would be a wise decision at all, not with all the constraints surrounding it. Best to keep the Undertaker as is and continue booking him in big time WrestleMania matches for the next year or two before he finally decides to hang it up.